The Kafka Challenge: Translating the Inimitable

 

The Kafka Challenge

Translating the Inimitable

Paul Reitter

Paul Reitter is professor of German Languages and Literatures and former director of the Humanities Institute at Ohio State University and the author of The Anti-Journalist: Karl Kraus and Jewish Self-Fashioning in Fin-de-Siècle Europe and many other books. The most recent of his translations is Karl Marx’s Capital.

When I taught German in graduate school back in the late 1990s, my fellow instructors and I often used a line from Franz Kafka’s novel The Trial to illustrate a point about grammar that was also a point about untranslatability.¹ In German, as in English, the regular subjunctive form goes mainly with wishes, counterfactual conditions, statements, and questions, as well as with polite requests. But the German form has an additional function: It can mark speculation—or, really, ambiguity—in a way that’s hard to match in English. Kafka’s line evokes a vivid sense of this gap, which, in the first place, is why we turned to it here. However, we had further reasons for doing that, starting with the fact that untranslatability is one of Kafka’s great themes. 

Untranslatability is also one of George Steiner’s great themes—and one of his central concerns in his commentary on Kafka. It would be hard to think of a literary scholar or critic who has done more to draw attention to this aspect of Kafka’s work, to reveal it as a guiding principle. In his essay “K,” for instance, Steiner cites, at length, a previously underexamined diary entry in which Kafka discusses how for him the German words Mutter and Vater fail “to approximate to” Jewish mothers and fathers. Kafka suggests that his psychic life was shaped by this linguistic misalignment; as a result of it, he “did not always love” his mother as “she deserved” to be loved and as he was capable of loving her. Steiner goes on to read “The Burrow,” one of Kafka’s last stories, as “a parable” of “the artist unhoused in his language,” a point he makes to explain nothing less than “the fantastic nakedness and economy” of Kafka’s prose.²

In After Babel (1975), which appeared more than a decade after “K,” Steiner went further still, deepening his engagement with how “the theme of Babel haunted” Kafka, who felt himself to be caught between the incompatible impossibilities of “writing in German” and “writing differently.” He traces the theme through a number of Kafka’s works, including “The Great Wall of China” and “The Burrow,” that enigmatic late work on the way in which the apt metaphor for verbal communication is less a building of bridges to the world than the creation of structures that seal us off from it.³ “In Kafka,” as Steiner puts it, “speech is the paradoxical circumstance of man’s incomprehension.”⁴ Borrowing a phrase from the historian Gershom Scholem, he elsewhere calls Kafka a “borderline case of wisdom, representing, as no other writer has, ‘the crisis of the sheer transmissibility of truth.’”⁵

Josef K. in the Dock

Against this background, in the late 1990s the prospect of new English translations of Kafka’s novels The Trial and The Castle, the first done by scholars—Breon Mitchell and Mark Harman, respectively, and the first to be based on unexpurgated manuscripts—elicited excitement but also skepticism. There was no shortage of the latter attitude among graduate students of German, and I remember feeling both disappointed and vindicated when Mitchell’s rendering of The Trial appeared in 1998 and I saw that he hadn’t fared much better than Willa and Edwin Muir with the line we enlisted to stress the difficulty of the subjunctive. Our suggestions about its untranslatability had held up. 

If anything, Mitchell’s translation appeared to be less effective than the Muirs’ original English version (1937), which made the line seem all the more well-suited for the role we assigned it. The first sentence of The Trial reads, in German, “Jemand mußte Josef K. verleumdet haben, denn ohne daß er etwas Böses getan hätte, wurde er eines Morgens verhaftet.” (“Someone must have slandered Josef K., for without having done anything wrong, he was arrested one morning.”⁶) The subjunctive form is “hätte,” which, when paired with a past participle (e.g., “getan”), would most often be translated as “would have” or “had,” as in “if he had done something wrong, we would have found out,” or “if only he had done something wrong.” Neither a condition nor a wish nor a request in the case at hand, it signals, unobtrusively but importantly, that we don’t have here an unambiguous statement of fact. Josef K. may have “done something wrong” (“etwas Böses getan”), or maybe not. Maybe the narrator knows but is not saying whether it’s one way or the other, and the more decisive first and last parts of the sentence—“Someone must have slandered Josef K.,…he was arrested one morning” (“Jemand mußte Josef K. verleumdet haben…wurde er eines Morgens verhaftet”)—don’t ultimately make it all clear. 

This element of uncertainty is not preserved in the Muirs’ rendering. Since it turns on a use of the subjunctive that, you could say, lies outside the cognitive field of the English counterpart feature, you can’t keep it without resorting to paraphrase—“even though he may not or would not have done anything wrong”—which still points too much in the direction of guiltlessness. In the Muirs’ translation, Josef K. is thus introduced as someone who was arrested one morning “without having done anything wrong.” He’s presented as a victim, in other words, and Anglophone readers have tended to see the book as being about an innocent man who is arrested and punished by a bizarrely opaque and capricious legal system. This, for example, is how the novel has been portrayed in US legal reasoning, where it has figured more prominently than you might think. According to one estimate, “Since the mid-1970s…Kafka’s name has appeared in more than 400 opinions written by American state and federal judges.”⁷

Mitchell tried to finesse the situation, following the Muirs into the indicative mood but inserting the word “truly” into the sentence, so that Josef K. is arrested “without having done anything truly wrong.”⁸ He’s no longer simply innocent: Mitchell’s translation tells us that Josef K. may have transgressed, just not in a substantial or serious way. In essence, then, Josepf K. remains a victim, only now we have to contend with a distinction that plays no role in the German text: something wrong versus something truly wrong.

So if there is a politics to this particular instance of untranslatability—one that has to do with things postwar critics haunted by totalitarianism prized in Kafka, among them Steiner and Theodor Adorno, things such as developing in readers a capacity to live with doubt, or, perhaps, to understand that interpretation involves overreach and thus guilt—then it is a fragile politics. Necessarily, the political content changes in English, and the consequences for Kafka’s Anglophone reception have been significant. 

The Kafkaesque Untranslatables

In the years after Mitchell’s translation was published, untranslatability won greater prominence as a topic in literary studies, thanks in large part to the work of the scholar Barbara Cassin, whose 1,344-page Dictionary of Untranslatablesappeared in French in 2004 and as an expanded English edition ten years later.⁹ Like Steiner, and Kafka, too, Cassin stopped short of making untranslatability “a criterion of truth.” But her project, carried out with scores of collaborators, certainly thickened the association between untranslatability and semantic depth and heft, since the list of terms included—they are all terms with a place in the history of philosophy—reads like a who’s who of philosophical key terms: e.g., “Geist” and “Dasein.” During this time, as the English retranslations of Kafka kept coming, I continued to think about the translation challenges his works pose, or, as Cassin says with reference to philosophical untranslatables, about how the translation of his works can “create a problem.” It seemed, and still seems, like a productive way to reflect on his writing and the sources of its special appeal. 

Consider what happens when we compare two recent translations of The Metamorphosis—Susan Bernofsky’s, from 2014, and Mark Harman’s, from 2024. The novella begins with Gregor Samsa waking up to find that he has been transformed into a “monstrous insect.” This turn of events clearly comes as a surprise, one that perplexes Gregor, prompting him to ask, “What has happened to me?” But he never follows up on his question, and it’s another unexpected occurrence, which he notices a little later, that leaves Gregor truly baffled and looking for answers: He has overslept. He wants to know how he could have done that, as well as what the best way to respond might be. Here, in Harman’s translation, are a few sentences from this part of the story:

Shouldn’t the alarm clock have rung? He could see from his bed that it was correctly set for four o’clock; surely it must have rung. Yes, but was it possible to sleep through this furniture-rattling alarm? Well, he had certainly not slept quietly, but probably all the more deeply for that. But now what should he do? The next train left at seven o’clock; to catch up with it he would have to hurry like mad, the cloth samples were not yet packed, and he certainly didn’t feel especially fresh and active. And even if he caught up with the train, it would be impossible to avoid a tongue-lashing from the boss, for the office assistant would have been waiting beside the five o’clock train and would have reported his negligence long ago.¹⁰

And here are the same sentences in Bernofsky’s translation:

Could the alarm have failed to ring? Even from the bed one could see it was properly set for four o’clock; it must have rung. Yes, but was it possible to sleep tranquilly through this furniture-shaking racket? Well, his sleep hadn’t been exactly tranquil, but no doubt that’s why it had been so sound. But what should he do now? The next train was at seven o’clock; to catch it, he would have to rush like a madman, and his sample case wasn’t even packed yet, and he himself felt far from agile or alert. And even if he managed to catch this train, his boss was certain to unleash a thunderstorm of invective upon his head, for the clerk who met the five o’clock train had no doubt long since reported Gregor’s absence.¹¹

Right from the start—“Could the alarm have failed to ring?” versus “Shouldn’t the alarm clock have rung?”—we see that Bernofsky opts for a more formal register. Since we are sliding into Gregor’s perspective, and thus getting the phrasing in his head, this makes for a little more wackiness—the monstrous insect with the genteel formulations: “Even from the bed one could see,” “tranquilly,” “rush like a madman,” “thunderstorm of invective upon his head.” Not only is the diction in Harman’s rendering less elevated, but the prose tends toward greater compression—“he could see,” “hurry like mad,” “tongue-lashing,” “would have reported his negligence long ago” versus “had no doubt long since reported Gregor’s absence.” Similarly, Harman’s syntax is a little less complex, and as a result of these differences, the sentences in his translation move forward faster. 

In the German, the repetition of words is more conspicuous than it is in both translations. Kafka uses the same word for “ring/noise” (“läuten”) in three consecutive sentences. Both translators reduce that to two occurrences and the two occurrences of “ja” (“yes”) to one. The word “selbst” is employed two different ways (“himself” and “even”) in consecutive sentences, which makes the repetition difficult to preserve. But, unlike Harman, Bernofsky compensates for that loss by repeating a phrase (“no doubt”) where there isn’t repetition in the source text. Furthermore, she keeps the doubling of the term “ruhig” (“tranquil” in her translation), whereas Harman doesn’t, and in contrast to him she retains all three instances of “and” (“und”) in the last two sentences, thereby reproducing more of the dynamic of prose cycling around. 

The differences with respect to forward thrust and repetition bring us to the key translation challenge: Kafka’s sentences manage to be both recursive and propulsive. Gregor’s thoughts wind around and around, and yet even many of the longer sentences drive forward, since as he repeats words, Kafka takes advantage of resources for compression that we lack in English (e.g., gendered nouns and heavy case inflection make it possible to lean on pronouns without risking confusion). Because the recursive element plays the greater role in producing the atmosphere readers have come to think of as “Kafkaesque,” which is characterized in part by recursive reflection going on where you don’t expect it to (the former traveling salesman wondering in detail about how he could have overslept and ignoring the matter of how he turned into an insect), translators have made conveying it a priority. 

Harman’s bold move in his translation of The Metamorphosis, which he calls The Transformation, is to back away from this priority—not a lot, but perceptibly—and to allow the propulsive character of Kafka’s prose to be brought into English more fully. As a longtime reader of that prose, I had certainly experienced the tension in its sentences between two contrasting, even opposing, kinds of movement. But the tension didn’t come into relief for me as something I was consciously aware of until I thought about how Harman’s translation differs from earlier ones and about the reprioritization—whether intentional or not—his project entails. 

When we compare the versions of The Metamorphosis by Harman and Bernofsky, we encounter another pair of dichotomous tendencies, which is perhaps even more striking. Neither version manages to preserve the full effect of Kafka’s sentences—the translation of his work does indeed “create a problem”—and yet both renderings are excellent: careful, thoughtful, and polished. They give us a Kafka who is recognizably himself. In fact, for an author so much associated with radical singularity, linguistic self-alienation, and Talmudic indeterminacy, or, in a word, untranslatability, Kafka has proven to be remarkably translatable.¹²

Parables Without a Key

The Muirs’ translations are still used, appreciated for what Steiner himself described, in speaking of their version of The Trial, as a certain “freshness of encounter,” by which he may have meant they preserved the antic mood one finds so often in the social world of Kafka’s fiction. But there are now many other successful Anglophone efforts: Harman’s translations of The Castle (1998) and Amerika (2008), Idris Parry’s translation of The Trial (2000), J.A. Underwood’s translation of The Castle (1997), Michael Hofmann’s translations of Amerika (2002) and The Metamorphosis (2007), Anthea Bell’s translation of The Castle (2009), Shelley Frisch’s translation of Kafka’s aphorisms (2022), and Ross Benjamin’s translation of his diaries (2023), to name a few beyond the ones already mentioned. 

Part of what has brought about this situation, I think, is simply that Kafka, an uncompromising innovator with high-modernist aura and a broad readership, has attracted very talented, ambitious translators. Another part is that he maintained diverse allegiances. In this he bears an affinity with Steiner, who was devoted to modernist “Gnosticism,” to use his (Steiner’s) term, and who celebrated Walter Benjamin as a “theologian of language” with an unrivaled eye for the paradoxes of Kafka’s mysticism, yet whose own prose differs so starkly from Benjamin’s in terms of directness and limpidity. There is a side of Kafka that not only draws on the realist tradition of Dickens, Flaubert, Balzac, and Tolstoy, all writers whom he studied attentively, but also tries to streamline it. 

Compare the first lines of the 1912 short story “The Judgment,” which Kafka regarded as his best work, with the opening of Thomas Mann’s novella Death in Venice, which appeared the very same year and lifted Mann out of an extended writing slump. (The two stories have quite a bit in common, by the way, including the theme of deindividuation and the respective watery demises of their protagonists.) With his self-narrative breaking down more and more—he can hardly remember anything by the end of the story—Kafka’s Georg Bendemann hastens to carry out his father’s dramatic judgment: He hurls himself into a river, vanishing without a trace. (Mann’s Gustav von Aschenbach, exhausted by his lifelong struggle to balance the Dionysian and Apollonian tendencies within him, finds himself drawn irresistibly to the formless “liquid element.”¹³) Kafka gives us a series of lean, descriptive sentences with straightforward syntax: They begin with a subject followed immediately or nearly immediately by a verb and contain only a couple of subordinate clauses. Mann’s opening sentences are so full of extended modifiers and internal clauses that an acclaimed recent Anglophone translation simply drops one of those clauses for the sake of getting the sentences into literary English. In contrast to Mann’s fiction, moreover, Kafka’s largely avoids local references and also dialects, two things that can bedevil translators. Whereas Mann cultivated a musical style, at times echoing the rhythms of Wagner’s compositions, Kafka strove, as Mark Anderson has put it, to make his prose “non-musical,” even boasting of his “unmusical” nature in letters to his Czech translator Milena Jesenská.

But in at least one respect, the Kafkaesque itself, or the atmosphere that counts as that, lends itself to translation. It does so because this atmosphere depends, to a large extent, on structural conceits. That this is so should already be clear, in fact. Recall the passage where Gregor realizes he has overslept. Whatever an individual translator’s priorities may be, the basic incongruousness of Gregor’s response to his situation will likely come across in the translation because it is part of the structure of the scene: Again, Gregor puzzles over how he managed to oversleep rather than over the forces that metamorphosed him into a giant insect. Furthermore, the same goes for the strangeness of such an insect engaging not only in thought but in intricate, lawyerly, recursive thought, in which the doubts pile up—and even if x problem were solvable, what about y problem?—yet the most obvious problem is omitted. How can Gregor hope to pack up his samples, catch his train, and carry out his job, given that he no longer has a human body? 

Let’s consider the Muirs’ translation of the passage:

Had the alarm clock not gone off? From the bed one could see that it had been properly set for four o’clock; of course it must have gone off. Yes, but was it possible to sleep quietly through that ear-splitting noise? Well, he had not slept quietly, yet apparently all the more soundly for that. But what was he to do now? The next train went at seven o’clock; to catch that he would need to hurry like mad and his samples weren’t even packed up, and he himself wasn’t feeling particularly fresh and active. And even if he did catch the train he wouldn’t avoid a row with the chief, since the firm’s porter would have been waiting for the five o’clock train and would have long since reported his failure to turn up.¹⁴

As with the first sentence of The Trial, the Muirs are prepared to let subjunctive forms go here—for example, note their “Had the alarm clock not gone off?” as compared with Harman’s “Shouldn’t the alarm clock have rung?” and Bernofsky’s “Could the alarm have failed to ring?” The loss of the subjunctive doesn’t substantially alter the meaning in this case by eliding a crucial ambiguity, but neither is it an unimportant change. Holding a little closer to the German, as Harman and Bernofsky do with the slightly non-colloquial “Shouldn’t the alarm clock have…” and “Could the alarm have failed…,” and as Bernofsky does with “thunderstorm of invective” for Kafka’s “Donnerwetter,” whose non-metaphorical meaning is “stormy weather,” creates an air of linguistic scruple that matches Kafka’s. The Muirs’ “row” doesn’t begin to reproduce the vividness of Kafka’s expression and suggests “quarrel” when Gregor is unlikely to stick up for himself—hence Harman’s “tongue-lashing.” Such translation differences have cumulative effects, making for profoundly different reading experiences, and yet the point still stands: The Kafkaesque is palpable in all three translations. The structural conceits are of course present in all three, and if, as is often the case with first translations of works that become classics, the Muirs’ translation of the passage feels almost a little slapdash compared with the carefully weighed out later versions, it is at least as attuned to other basic elements of the Kafkaesque, such as repetition. 

Another of Kafka’s great themes is paradox—“plenty of hope, just not for us,” “what do I have in common with the Jews? I hardly have anything in common with myself.” And then there are the paradoxes of his work—parables without “a key,” to speak with Adorno, fiction so tied to a Czech-Jewish-German milieu and yet able to resonate with the most diverse audiences, to the point that an early biographer saw fit to describe Kafka as “representative man.” We can add this paradox to the list: eminently translatable, untranslatable.  

 

The Software Essays that Shaped Me

by Michael Lynch, published September 30, 2025

I started reading software blogs before I got my first programming job 20 years ago. At this point, I’ve read thousands of blog posts and essays about software, but only a small handful stuck in my mind and changed the way I think.

1. “The Joel Test: 12 Steps to Better Code” by Joel Spolsky (2000)
2. “Parse, don’t validate” by Alexis King (2019)
3. “No Silver Bullet - Essence and Accident in Software Engineering” by Fred Brooks (1986)
4. “Choices” by Joel Spolsky (2000)
5. “Application compatibility layers are there for the customer, not for the program” by Raymond Chen (2010)
6. “Don’t Put Logic in Tests” by Erik Kuefler (2014)
7. “A little bit of plain Javascript can do a lot” by Julia Evans (2020)
8. “Choose Boring Technology” by Dan McKinley (2015)
9. “I’ve locked myself out of my digital life” by Terence Eden (2022)
10. Bonus: Brad Fitzpatrick on parsing user input (2009)

“The Joel Test: 12 Steps to Better Code” by Joel Spolsky (2000)🔗

Joel Spolsky is the greatest software blogger of all time. His essays have informed so much of my approach to software that it was hard to pick out just one, but “The Joel Test” is my favorite.

The Joel Test is a set of 12 questions that employers can ask themselves to see how well they’re investing in their software team:

1. Do you use source control?
2. Can you make a build in one step?
3. Do you make daily builds?
4. Do you have a bug database?
5. Do you fix bugs before writing new code?
6. Do you have an up-to-date schedule?
7. Do you have a spec?
8. Do programmers have quiet working conditions?
9. Do you use the best tools money can buy?
10. Do you have testers?
11. Do new candidates write code during their interview?
12. Do you do hallway usability testing?

Some of the questions are dated, but the point was never the questions themselves but rather the meta-point of the questions.

Joel was really asking employers: do you respect developers?

The questions all assess whether an employer prioritizes their developers’ time and focus over things like cheap office space and short-term deadlines.

Joel published this article at the height of the dot-com boom, when skilled developers were a precious resource, but not everyone realized it, including developers themselves.

Joel’s blog always presented programmers as rare, delicate geniuses that employers needed to pursue and pamper. I liked that.

Throughout my career, I sought out employers that scored well on the Joel test, and I’m grateful to Joel for giving me the map to find them.

“Parse, don’t validate” by Alexis King (2019)🔗

This essay is about leveraging the type system in Haskell to — wait, wait! Don’t go to sleep.

If you don’t care about type systems or Haskell, I get it. I don’t either. But this essay radically changed the way I think about software. You can use Alexis’ technique outside of Haskell in any language that supports static types (e.g., Go, C++, Rust).

The highly abridged version of the essay is that whenever you validate any data, you should convert it to a new type.

Suppose that your app has a rule limiting usernames to a maximum of 20 alphanumeric characters. The naïve solution would be to define a function that looks like this:

func validateUsername(username string) error { ... }

With the above function, you run validateUsername anytime you receive a username from a user.

The problem with this approach is that your code is unsafe by default. You have to remember to validate every username you receive, so it’s easy to create a code path that accidentally processes a username without validating it. If a nefarious user notices the mistake, they can do tricky things like embed malicious code in the username field or stuff it with a billion characters to exhaust server resources.

Alexis’ solution is to instead use a function like this:

func parseUsername(raw string) (Username, error) { ... }

In the rest of your codebase, instead of passing around a string called “username,” you use a custom type: Username. The only function that can create a Username is parseUsername, and it applies validation rules before returning a Username instance.

Therefore, if you have a Username instance, it must contain a valid username. Otherwise, it couldn’t exist.

You can’t forget to validate a username because untrusted input will always be a string, and you can’t pass a string to a function that expects a Username.

Before Alexis’ essay, I thought type systems were just a fun way to distract language nerds. “Parse, don’t validate” opened my eyes to how valuable compiler features can be in improving an application’s security and reliability.

“No Silver Bullet - Essence and Accident in Software Engineering” by Fred Brooks (1986)🔗

In college, I read The Mythical Man-Month, a collection of essays about software engineering by Fred Brooks, drawing on his experience directing IBM’s OS/360 project.

The essays were hit or miss. Some felt too old to be relevant, even in 2002, but the one that stuck with me was, “No Silver Bullet.”

The essay argues that you can divide software work into two categories: essential complexity and accidental complexity.

Essential complexity is the work that you absolutely have to do, regardless of your tooling and hardware. For example, if you write software that calculates bonuses for salespeople, you have to define formulas for those bonuses and cover all possible edge cases. This work is the same if you have a $5B supercomputer or a $1 microcontroller.

Accidental complexity is everything else: dealing with memory leaks, waiting for your code to compile, figuring out how to use a third-party library. The better your tooling and hardware resources, the less time you spend on accidental complexity.

Given this model, Brooks concluded that it was impossible for any advancement in tooling or hardware to create a 10x improvement in developer productivity:

How much of what software engineers now do is still devoted to the accidental, as opposed to the essential? Unless it is more than 9/10 of all effort, shrinking all the accidental activities to zero time will not give an order of magnitude improvement.

Throughout my career, people have been trying to find ways to eliminate programmers from software. For a few years, no-code platforms generated buzz by promising non-programmers all the powers of a seasoned web developer.

Brooks’ essay always reassured me that the latest buzzword platforms could never replace developers, as the platforms focused on the accidental, not the essential. Even if the platforms could magically create working code from a functional specification, you still need someone to write the spec:

I believe the hard part of building software to be the specification, design, and testing of this conceptual construct, not the labor of representing it and testing the fidelity of the representation.

Modern AI has thrown a wrench into Brooks’ theory, as it actually does reduce essential complexity. You can hand AI an incomplete or contradictory specification, and the AI will fill in the gaps by cribbing from similar specifications.

Even if AI eliminates programming as we know it, Brooks’ essay gives me hope that we’ll still need people to manage essential complexity at whatever level of abstraction that ends up being.

“Choices” by Joel Spolsky (2000)🔗

I said above that it was hard to pick a single favorite Joel Spolsky essay, which is why I’ve chosen two.

“Choices” is about creating user interfaces and the subtle costs of giving a user power:

Every time you provide an option, you’re asking the user to make a decision. That means they will have to think about something and decide about it. It’s not necessarily a bad thing, but, in general, you should always try to minimize the number of decisions that people have to make.

As an example, Joel shares a ridiculous dialog that appears in Windows 98 when you try to search the help documentation:

The dialog infuriates Joel because it interrupts the user while they’re trying to get help, and it asks them to make an uninformed decision about database optimization. Windows was shirking a decision and pushing it onto the user.

Joel’s essay focuses on graphical user interfaces, but I think about it wherever people might encounter my code, including on the command-line or other developers calling functions I wrote. Can I make a useful decision on my user’s behalf while still giving them power over things they care about? There are countless times where Joel’s essay has saved me from pushing a decision onto the user that I could make myself.

“Application compatibility layers are there for the customer, not for the program” by Raymond Chen (2010)🔗

Raymond Chen is one of the longest-serving developers on the Microsoft Windows team. His blog has thousands of informative, entertaining stories about the history of Windows programming, but the one I think back to most is one about compatibility mode in Windows Vista.

A customer had contacted Raymond’s team with this request:

Hi, we have a program that was originally designed for Windows XP and Windows Server 2003, but we found that it runs into difficulties on Windows Vista. We’ve found that if we set the program into Windows XP compatibility mode, then the program runs fine on Windows Vista. What changes do we need to make to our installer so that when the user runs it on Windows Vista, it automatically runs in Windows XP compatibility mode?

Raymond proceeds to characterize the customer’s request as follows:

I normally toss my garbage on the sidewalk in front of the pet store, and every morning, when they open up, somebody sweeps up the garbage and tosses it into the trash. But the pet store isn’t open on Sundays, so on Sundays, the garbage just sits there. How can I get the pet store to open on Sundays, too?

I loved this analogy. The metaphor was so funny that I didn’t notice until just now that Raymond is in the wrong. He’s making fun of a developer whose sin is expecting Windows not to break their app after a single release.

But as is the case with a lot of Raymond Chen’s writing, it’s so funny and sharp that I can look past the flaws.

Even though I disagree with the specifics, Raymond’s post is an excellent lesson in influencing user behavior.

If you want to nudge the user to do something that helps you, think carefully about the path of least resistance from the user’s perspective, because that’s the path they’ll take.

If you show the user that dumping garbage on the sidewalk completely solves their problem, they’re going to keep dumping their garbage on the sidewalk.

“Don’t Put Logic in Tests” by Erik Kuefler (2014)🔗

I’ve always loved unit testing and took great pride in my test code. That’s why I was so horrified when this essay appeared in my bathroom and revealed that I’d been writing awful tests my whole career.

Erik’s essay shows the following unit test, which has a subtle bug:

@Test public void shouldNavigateToPhotosPage() {
  String baseUrl = "http://plus.google.com/";
  Navigator nav = new Navigator(baseUrl);
  nav.goToPhotosPage();
  assertEquals(baseUrl + "/u/0/photos", nav.getCurrentUrl());
}

When I first read the essay, I thought, “That’s exactly how I write unit tests!”

Why duplicate the http://plus.google.com/ string in two places? Create a single source of truth, just like in production code. I did this all the time, adding helper functions, variables, and loops to eliminate redundancy from my tests.

The problem with the approach above is that it masks a subtle bug. It’s actually asserting that the URL looks like this:

http://plus.google.com//u/0/photos
                      ^^
                    whoops

Erik’s essay showed me that I shouldn’t treat test code like production code at all. The two have completely different goals and constraints.

Good test code should be, above all, clear. Test code doesn’t have its own test code, so the only way to verify correctness is by inspection. A test should make it blindingly obvious to the reader what behavior it asserts. In service of that goal, you can accept redundancy to reduce complexity.

“A little bit of plain Javascript can do a lot” by Julia Evans (2020)🔗

As a software engineer, I was embarrassingly late to the web. For the first 10 years of my career, I only wrote code for desktop apps and backend servers. I never bothered with HTML or JavaScript until 2017.

By the time I got serious about learning frontend development, my impression was that JavaScript was a mess of a language, hacked together in 10 days, and it had drastically different behavior in different browsers. If I was going to write web apps, I wanted something modern and sleek to protect me from all of JavaScript’s bile and warts.

So, I tried the popular web frameworks of the day: Angular, React, and Vue. I learned enough Vue to make my way around, but I was still spending an enormous amount of my time on dependency issues and framework gotchas. After all the work these frontend frameworks did to fix JavaScript, web programming still sucked.

Then, I read Julia’s essay and realized I’d been so confident that JavaScript needed fixing that I never gave it a chance.

At the time, I was working on the prototype of TinyPilot, which would become my first commercially successful software product. TinyPilot had a web interface that I was planning to implement with Vue, but Julia’s essay inspired me to see how far I could go with plain JavaScript. No framework, no wrapper libraries, no build step, no Node.js, just regular old JavaScript. Okay, not “old” — more like ES2018, but you know.

I kept expecting to hit some problem where I’d need to switch to some kind of framework or builder, but it never happened. There were still some gotchas, especially around WebComponents, but it was nothing compared to the suffering I endured with Vue and Angular.

I loved being free of the frameworks. When I had a runtime error, the stack trace wasn’t some minified, transmogrified, tree-shakified fever dream of my code. I was debugging my code, exactly as I wrote it. Why hadn’t I tried this sooner?

My biases about JavaScript were wrong. Modern JavaScript is pretty nice. It absorbed a lot of ideas from wrapper libraries, so now you don’t need the wrappers. And browsers got their act together to ensure consistent behavior across platforms and devices.

I haven’t integrated a JavaScript framework or build step into any new project since 2020, and I’ve never looked back. Plain JavaScript gets me 90% of the benefit of frameworks with 5% of the headache.

“Choose Boring Technology” by Dan McKinley (2015)🔗

This is an odd essay to include in this list because I’ve never actually read it.

People have quoted this essay to me, and once I understood the idea, it felt so intuitive that I didn’t need to read it. In my interview with CoRecursive podcast host Adam Gordon Bell, he talked about how there are certain non-fiction books where, once you understand the idea, all you need is the title. “Choose Boring Technology” is that for me.

Dan’s argument is that when you start a new project, you’re tempted to use cutting-edge technology that has lots of buzz. Google just announced a new database that scales to exabytes, and it’s 40% faster than Postgres at 20% the cost. You’d be an idiot to use Postgres when this sexy new alternative is right there!

In practice, the new technology has bugs and weaknesses, but they’re not obvious to you yet; they’re not obvious to anyone yet. So, when you run into them, you’re stuck. Postgres has its issues, but after 30 years in the field, it has battle-tested solutions for any problem you’re likely to encounter.

Dan concedes that you should use new technologies sometimes but only strategically and in limited quantities. He suggests that every business gets three “innovation tokens” to spend. If you want a flashy new database, you’ll have to spend one of your tokens.

Dan’s essay dovetails naturally with Julia’s essay. I wish I’d read either of them before I wasted all that time with frontend frameworks.

“I’ve locked myself out of my digital life” by Terence Eden (2022)🔗

Terence Eden is a delightful and eclectic technology blogger. He writes several new posts each week, but the one that impacted me the most was “I’ve locked myself out of my digital life.”

The article plays out what would happen if lightning struck Terence’s house and destroyed all of his possessions. He keeps his passwords to everything in a password manager, but if all his devices get destroyed, he can’t access his password manager. And he can’t fall back to hardware passkeys because those were in his house, too.

I always felt like I was pretty safe about my data because I store everything on redundant drives, and I have offsite backups on three continents with two vendors.

Terence’s post got me thinking about the many credible threats that could wipe out all of my devices simultaneously: fire, flood, electrical surge, criminal investigation. All of my data is encrypted with passwords that live in my head, so add to that list memory loss, incapacitation, or death.

Online services are bad at helping users recover from disaster. I use several services that assume it’s impossible for me to ever lose my phone, let alone my email account and every digital device in my possession.

Ever since I read Terence’s essay, I’ve been thinking more about which services and devices are critical to me, and how I could recover from a scenario like the one Terence described. The next time I bought a laptop, I set it up at the library to test whether I could recover access to my password manager and critical accounts without any of the devices in my house.

I still could do a better job at digital disaster preparedness, but Terence’s post always echoes in my head whenever I think about how to secure my devices and data. What if everything was suddenly destroyed?

Bonus: Brad Fitzpatrick on parsing user input (2009)🔗

It’s technically not an essay, but there’s a quote from a software interview I constantly think about.

In 2009, as a result of Joel Spolsky’s gushing review, (yes, again with the Joel), I read Coders at Work, a collection of interviews with accomplished programmers.

Brad Fitzpatrick, creator of LiveJournal and Memcached, appears in the book as one of the interviewees. He was only 28 years old at the time, the youngest programmer in the book and also the sweariest and most entertaining.

In response to a question about ethics in software engineering, Brad goes on an impassioned rant about input validation:

I would like to ask that everyone is consistent on their credit-card forms to like let me put in fucking spaces or hypens. Computers are good at removing that shit. Like don’t tell me how to format my numbers.

-Brad Fitzpatrick, in Coders at Work

I think back to this quote whenever I try to paste a phone number into a web form, and it whines that parentheses or spaces aren’t allowed. Or worse, it truncates my phone number because of the parentheses, and also complains that parentheses aren’t allowed.

Whenever I create input fields in my software and think about unexpected characters, I hear Brad Fitzpatrick say, “Computers are good at removing that shit.”

 

The 25 Most Influential Magazine Covers of All Time

NY Times · Michael Snyder · October 1, 2025

T 25

Four editors, a creative director and a visual artist met to debate and discuss the best of print media — and its enduring legacy.

T 25

Four editors, a creative director and a visual artist met to debate and discuss the best of print media — and its enduring legacy.

By Kurt SollerLiz BrownJason ChenJames DraneyMiguel MoralesLaura Regensdorf and

• Oct. 1, 2025Updated 10:58 a.m. ET

Despite all the groaning that “print is dead,” many people seem captivated by magazines lately: When Anna Wintour relinquished her editorship in June of Vogue, which she’s overseen for 37 years, it was national news; a memoir by the former Vanity Fair editor in chief Graydon Carter and a dishy nonfiction chronicle (by the New York Times reporter Michael M. Grynbaum) of Carter’s ex-employer, the luxury magazine publisher Condé Nast, made many summer reading lists. And even if magazines don’t hold the same cultural sway — or profits or attention spans — they once did, it’s undeniable that the people who make them, and the stories and images they’ve made, still have much to show us, not just about how we read and see, but about how we live. This has been true for nearly two centuries: Popular magazines like Scientific American and The Atlantic have both been continuously published since the mid-1800s.

The panel, from left: T’s creative director, Patrick Li; the artist Martha Rosler; the New Yorker editor David Remnick; the editor Adam Moss; T’s deputy editor, Kurt Soller (the conversation’s moderator); and the Oprah Live editor and broadcast journalist Gayle King, photographed at The New York Times on May 19, 2025.Credit...Eric Helgas

A magazine is nothing without its cover, of course. That’s why, for the latest installment of our T 25 series, we convened a panel of experts — Gayle King, 70, who, in addition to co-hosting CBS Mornings, is the editor at large for Oprah Daily, the current version of O, the Oprah Magazine; Patrick Li, 56, T’s creative director; Adam Moss, 68, the former editor of New York magazine and, before that, The New York Times Magazine; David Remnick, 66, the editor of The New Yorker; and Martha Rosler, 82, a New York-based conceptual artist whose work has long commented on and incorporated magazines and other forms of mass media — to choose the most influential magazine covers of all time. Before they submitted their own long lists of at least 10 nominees, I’d told them that they could select one another’s work but not their own. We also decided to limit the conversation to English-language publications, although the unranked list of 25 covers that follows, which we fought over in a Times conference room for several hours on a rainy May afternoon, includes only American publications.

That doesn’t mean we overlooked the importance of British magazines (see all of the panelists’ nominees here, with further commentary), notably the 1990 issue of The Face on which a 16-year-old model named Kate Moss debuted. But it was scrapped in favor of covers that were both more indelible — “I want people looking at this list and going, ‘Oh, yes, I remember that,’ ” King says — and more reflective of a time when magazine covers both broke and drove the conversations of the day, whether in politics, culture, fashion, food, sports or other realms. What you won’t find below, for example, are any Covid-19 covers, in part because, as Remnick says, “at a certain point, you start to reach an image proliferation [online], and so you can’t help but feel that the internet undermines the power of magazines in various different ways.” Also omitted: digital-only covers that have become popular in recent years as magazines have evolved beyond their native format.

Originally, we’d hoped to restrict the finalists to one per magazine, but as we kept debating, it became obvious that some titles had more impact than others — either because they inspired countless magazine editors and art directors, or because they were able to capture and harness a national moment in a way that feels impossible in our more fragmented era, or because they were run by teams of people all willing to court controversy and take the risks necessary to produce lasting creative work. “It’s hard to say they’re influential, but what does influential mean anyway?” Moss asked the group in an email he sent after our meeting. He was defending some 1930s Fortune covers he’d brought up but also, I think, encapsulating the project as a whole: “That was the question we were all grappling with, to little resolution. These don’t clarify our answer, but they’re very cool, and it’s just a game, anyway.” — Kurt Soller

This conversation has been edited and condensed. Though numbered, the entries below aren’t ranked; the covers appear roughly in the order in which they were discussed.

David Remnick: [The nominations] were surprising to me, because there are some that are always listed. It was nice to see things I hadn’t seen before.

Adam Moss: My feeling is some covers are famous for a reason, so we shouldn’t disqualify them.

Patrick Li: I think we’re going to see a lot of provocative images. And that makes a great cover. But now [with technology], if you can imagine that image, you can easily will it into being.

Moss: An amazing cover is [expletive] hard to do, so even if you can imagine an image …

Remnick: I discovered this with politics. You’d think in the age of Trump, the world would be filled with great political images.

Gayle King: You know what I liked about looking at our covers, guys? There were so many where I said, “I almost picked that one.”

Li: Before you came in, Gayle, we were talking about technology and AI and how easy it could be to make some of these images now, like Andy Warhol in a can of Campbell’s Soup [for Esquire’s May 1969 issue]. So how is everything going to change? Can we still rely on the shock of an image to make it one of the best covers? I’m also interested in how these kinds of images represent the brand of the magazine.

Moss: That’s very important, and that comes with consistency, obviously.

1. Muhammad Ali, Esquire, April 1968

Credit...Created by George Lois. Photo by Carl Fischer, courtesy of Esquire

In late 1967, months after Muhammad Ali refused a U.S. Army draft order on religious grounds and found himself excommunicated from boxing for the next three years, he slipped back into a pair of shiny white Everlast shorts. He was on set for Esquire with the photographer Carl Fischer and the art director George Lois — the adman provocateur and freelance art director whose genius for landing a visual punch defined the magazine’s covers in the ’60s. (He memorably put an ironic halo on Joe McCarthy’s lawyer Roy Cohn, among other things.) Here, the goal was to convince the Muslim athlete to assume the role of Saint Sebastian, with Francesco Botticini’s c. 1465 painting of the martyr as a particular reference point. After Ali agreed, they just had to figure out how to realistically stick him with a half-dozen arrows, an effect achieved with a combination of glue and fishing line. Once known for his trash-talking bravado, the boxer had emerged as a celebrity athlete with a cause: “I’m taking a stand for what I believe in and being one thousand percent for the freedom of the black people,” he told the writer Leonard Shecter in the accompanying story. Soon after the issue arrived on newsstands, Martin Luther King Jr. was killed, giving the photograph a prophetic charge. — Laura Regensdorf

The photographer Carl Fischer, creating one of Muhammad-Ali-as-Saint-Sebastian’s fake wounds on the Esquire set.Credit...Courtesy of the Carl Fischer Archives

Remnick: That was one of the great lunches of my life — George Lois.

Moss: I mean, he was fun. He was incredibly, you know, self-regarding, but …

Remnick: And it’s only a very short period of time that he [makes Esquire’s covers], like [10] years or so.

Moss: [Esquire’s editor] Harold Hayes would meet with him over the contents of the issue, and George would say: “I think I could make something out of this [story].” He’d send it back to Hayes, who wasn’t allowed to veto him more than once.

Kurt Soller: And they were such craft projects.

Remnick: If you really had to pick a master of magazine covers … and I think George Lois would rise from the dead and agree with me.

Moss: I agree with David on this, but that’s because Esquire was what I grew up with: I’m highly influenced by the fact that a magazine’s job was to have a point of view; this was the magazine that taught me all magazines ought to.

Remnick: And the timing of the [Ali cover]: He’s been alienated, he’s a martyr, he’s Saint Sebastian —

Moss: It would be a decision [for us to choose this over Warhol in the soup can, also by Lois], which in some ways is the most famous magazine cover of all time.

Soller: But is there something to be said, though, about covers that push the boundaries of good taste? About doing things that you maybe couldn’t get away with today?

2. “If You Don’t Buy This Magazine, We’ll Kill This Dog,” National Lampoon, January 1973

Credit...National Lampoon

A spinoff from The Harvard Lampoon, the university’s now 150-year-old humor magazine, National Lampoon launched in 1970 and quickly distinguished itself with an ethos that people found either amusing or appalling or both. Its most famous cover, for its “Death” issue in 1973, features an uneasy-looking dog, Mr. Cheeseface, with a gun held to his head and the line “If You Don’t Buy This Magazine, We’ll Kill This Dog.” National Lampoon frequently skewered politicians and celebrities — it ran a fake ad for a Volkswagen that floated like a water beetle, with the copy “If Ted Kennedy drove a Volkswagen, he’d be president today” — but here the staff were making fun of themselves as magazine makers. Covers are, after all, about compelling someone to pick up the issue, and why not satirize that with a desperate joke told at the expense of an adorable pet? Ed Bluestone, a stand-up comic and Lampoon staffer, came up with the idea; the picture was taken by the photographer Ronald G. Harris, who said that because Cheeseface is side-eyeing the revolver rather than staring straight ahead, the joke lands. The cover would inspire future magazines, from Spy to George, to keep testing the limits of satire. — Miguel Morales

National Lampoon co-founder Henry Beard, left, with magazine staffers in a still from the 2015 documentary “Drunk Stoned Brilliant Dead: The Story of the National Lampoon.”Credit...Courtesy of the Estate of David Kaestle/Magnolia Pictures

Moss: If you don’t have a reaction to a cover in some visceral, emotional way, it’s not working. So, yeah, sometimes that can be sophomoric — the National Lampoon cover is idiotically sophomoric. Fantastic cover.

Remnick: No dogs were killed in the making of this cover.

King: With the gun issue, I don’t know if you could get away with this today.

Soller: Also, Patrick, in terms of what you were saying about a cover representing the brand of a magazine —

Remnick: For us, that’s changed. There came a time in the early decades of The New Yorker under Harold Ross [who founded and ran the magazine from 1925 to 1951], where the covers were absolutely effervescent of New York and beautifully rendered. At a certain point, William Shawn wanted the covers to be anti-covers.

Moss: One great thing The New Yorker has going for it is that it has an illustrated cover style that’s nearly unique among all magazines at this point. That allows a certain amount of room for an editor to make it their own or for it to play in a moment without actually trashing the brand.

Soller: Is there a New Yorker cover that you all feel rises above the rest? And maybe David doesn’t get to decide on this.

3. “Moment of Joy,” The New Yorker, July 8 & 15, 2013

Credit...Jack Hunter. Cover: courtesy of The New Yorker

In June 2013, a pair of Supreme Court rulings (in Windsor v. United States and Hollingsworth v. Perry) established states’ rights to protect marriage equality, leading to the federal recognition of same-sex unions two years later. To mark the moment, The New Yorker chose an updated version of a cover illustration that the American artist Jack Hunter had submitted to a Tumblr account run by the magazine’s longtime art editor, Françoise Mouly, and her daughter, Nadja Spiegelman. The final cover showed the beloved odd couple of “Sesame Street,” Bert and Ernie, who’ve shared an apartment since 1969, sitting in a darkened living room, Ernie’s head resting on Bert’s shoulder, their silhouettes illuminated by a televised image of the nine justices in black and white. Rather than being explicitly celebratory, the image was muted and domestic. It winked at long-swirling speculation around the characters’ relationship status (“Sesame Street”’s production company’s response, from 2011: “Even though they are identified as male characters and possess many human traits and characteristics […] they remain puppets, and do not have a sexual orientation”) while validating the experience of the many queer couples who’d followed the cases with hope and trepidation. The image was not without its detractors, who claimed the magazine had trivialized a long legal struggle. But for many others, Hunter’s sweet and earnest cover expressed the true impact of the court’s decision. — Michael Snyder

Moss: Bert and Ernie — when The New Yorker is able to do its thing and intersect with something extremely topical …

King: And look at what they’re watching.

Remnick: And Bert and Ernie, that joke had been made for years.

Moss: It’s a perfect New Yorker cover of David’s days, and it’s a beautifully executed picture.

Li: It works on so many levels and it speaks to so many different audiences. It’s really good — and it educates people.

4. Ellen DeGeneres, Time, April 14, 1997

Credit...Firooz Zahedi/courtesy of TIME

The ABC sitcom “Ellen” had wrapped its third season and concern was growing within the network and its parent company, Disney, over a decline in viewership. DeGeneres later recalled Disney chief Michael Eisner proposing a solution: Ellen Morgan, the show’s protagonist, should get a dog. DeGeneres had a better idea, one that would solve the show’s identity problem and her own: She and her on-screen alter-ego would reveal they were gay. Her chosen platform was the cover of Time magazine (which then had a circulation of roughly four million) on which readers saw a beaming DeGeneres and the line “Yep, I’m Gay.” That combination of words — casual, declarative and written in the first person — suggested a future where coming out, even as a TV star, would be much less newsworthy. Unfortunately, the public wasn’t fully there yet, as evidenced by some letters to the editor. “Your report was an affront to decency in general and the troubled family unit in particular. … Shame on you, Time!” read one of them. DeGeneres shared the cover on social media in 2022, on the 25th anniversary of the issue, which by that point was widely understood to have eased the way for others wanting to live more freely. “I remember coming out,” she wrote, before joking, “I don’t, however, remember saying ‘Yep.’” — M.M.

Ellen DeGeneres coming out on the cover of Time became a punch line for late-night show hosts, including Jay Leno.

King: I still like Ellen’s “Yep, I’m Gay,” because saying that publicly was so shocking at the time — that it was the cover — and then she ended up being ostracized.

Moss: And the power of the word “yep” — I want to talk about language.

King: It wasn’t “yay” or “yes,” and it was spelled “y-e-p,” as opposed to “y-u-p.” I liked that.

Soller: Can we talk a little bit about the way a cover itself can create news? You know, this came out and then she came out on her show. When I was growing up, it was like this cover itself was the news. And Gayle, a lot of your covers are from Time.

King: I didn’t mean to do that, but I’m always drawn to their covers: I think they do a good job.

Moss: You think of “Is God Dead?” [in 1966]. They created a moment, rather than responded to a moment. Secularism had overwhelmed America, and Time, like Walter Cronkite, could make a statement, and then it would be true — or seem to be true.

Soller: Patrick, as the creative director here, from a design perspective, what do you think makes a text-only cover work?

5. “Oh My God — We Hit a Little Girl,” Esquire, October 1966

Credit...Created by George Lois. Cover: courtesy of Esquire

In December 1965, nearly a year after the U.S. first deployed combat troops to Vietnam, the reporter John Sack began basic training with the soldiers of M Company in Fort Dix, N.J. He didn’t come back from the experience opposed to the war, but in October 1966, when Esquire published his 33,000-word exposé about his journey with the men through the jungles of Vietnam, the narrative spoke for itself. On M’s first operation, a soldier launched a grenade into a hut and made the company’s first kill. “Oh my God — we hit a little girl,” said one of the men in horror. For the cover, Lois pivoted from his original design and printed that quote in bold white type on a black background. Few magazine covers force the viewer to consider the full weight of words alone. (Time’s text-only cover “Is God Dead?,” which had come out only six months earlier, may have inspired Lois). Here both the line and the styling captured the senselessness of the Vietnam War, while the “we” implicated the reader. It was among the first anti-Vietnam War magazine covers, and while you never see the girl herself, of course, you can’t read it without grieving for her. — Jason Chen

After George Lois, Esquire’s art director, read John Sack’s story about following American soldiers to Vietnam, he scrapped the cover originally planned for that month’s issue and sketched a replacement.Credit...© George Lois

Li: There are so few modern versions of [text-based covers], where it’s so minimal. But, “Oh my God — we hit a little girl,” that was amazing. It’s so indelible, right? Like this idea of the language becoming the image you create.

King: I was very drawn to the words. It made me think, “What is this about?”

Martha Rosler: Apologies, I’m late, the oral surgeon on Thursday told me I’d be fine by Monday.

Moss: I’ve also just come from the oral surgeon — emergency root canal.

Remnick: Blame it on The New York Times.

Soller: You just love magazines that much.

Li: We were talking about text-only covers — of course, typographically, I love seeing that.

Rosler: Me, too. I included a few ridiculous examples. There’s no such thing as most influential: Mostly my question is, will a cover appeal to its self-selected readers, and does it comport with what’s inside the magazine? So my point is that I’m noncompliant.

Remnick: That’s not what your dentist said.

Soller: But there was some overlap between you and Adam, for instance. You both picked Life’s fetus cover — you chose a lot from Life magazine, Martha.

6. “Drama of Life Before Birth,” Life, April 30, 1965

Credit...Lennart Nilsson, TT/Science Photo Library. Cover: courtesy of Life

In the early 1950s, the Swedish photographer Lennart Nilsson made a remarkable claim to the incredulous editors of Life: He was going to document the stages of human reproduction in full color. It took 12 years of experimenting with wide-angled optics and macro lenses, but he eventually made good on his word. In April 1965, the magazine published his extraordinary cover image of an 18-week-old fetus, luminous in its amniotic sac, seemingly floating through space, along with an extensive photo essay. Nilsson had worked closely with a Stockholm hospital, where he had a makeshift studio set up. He’d get a call when a woman had had a miscarriage or came in for an abortion, which had been legally permissible in Sweden since 1938 if the woman’s life was in danger. The photographer would then rush over with his Hasselblad camera. Only one image in the photo essay was of a live fetus in utero. All the others, including the groundbreaking cover, were of fetuses that had been surgically removed. In the 1980s, after learning that his pictures were being used at anti-abortion demonstrations, Nilsson refused to allow them to be republished. He continued to pioneer scientific photography, though, placing tiny cameras in flowers, tracking a coronary thrombosis and shooting close-ups of the H5N1 virus. When asked directly about his views on the beginning of life, Nilsson, who died in 2017, said, “It depends on yourself. I’m just a journalist telling you things.” — Liz Brown

Lennart Nilsson, the Swedish photographer who spent over a decade on his mission to document human life before birth, working in the studio he kept at Stockholm’s Sabbatsberg Hospital in 1965.Credit...Lennart Nilsson, TT/Science Photo Library

King: I remember this, too.

Rosler: That made a huge splash at the time. Also what’s interesting, of course, is that virtually all the fetuses that’re photographed are no longer extant. It was either post-abortion or miscarriage, which was not discussed much because it was a downer. You couldn’t say the word “abortion” in 1965, but definitely this had a huge impact.

Moss: I do think you have to distinguish between those covers that are themselves the thing [like many of Life’s most famous images] and those that are just responding to an incredible moment.

Soller: One of the interesting things about all of your nominees is there are many, for instance, Vietnam War covers. But there’s just one Covid cover, maybe because a lot of that imagery we’d already seen on the internet.

Remnick: There is a lot of Vietnam, but maybe that’s showing our childhoods.

Soller: Well, that was also the heyday of magazines.

Remnick: Watch your mouth.

7. “9/11/2001,” The New Yorker, Sept. 24, 2001

Credit...Art Spiegelman and Francoise Mouly/courtesy of The New Yorker.

On the morning of Sept. 11, 2001, Mouly and her husband, the cartoonist Art Spiegelman, had just left their SoHo apartment when they saw a plane fly into the North Tower of the World Trade Center. Soon after, the couple found themselves trying to distill the violence into a magazine cover. At first, Remnick’s art editor considered the idea of an entirely black cover: What kind of illustration could do justice to the attack? But within days the couple had come up with another idea — Spiegelman suggested some kind of black-on-black treatment, and Mouly mocked up a dark silhouette of the towers set against a slightly less varnished black background. Only in certain light would the lost buildings emerge. Mouly later explained that she’s “always been captivated by how a simple drawing can cut through the torrent of images that we see every single day.” Not only did the cover capture the emotional gravity of the event, but it also encapsulated the collective effort required to produce a magazine in difficult conditions: The magazine’s pre-press manager, Greg Captain, drove 15 hours to the Kentucky printing press to ensure the ink densities achieved just the right effect. — James Draney

The married collaborators behind The New Yorker’s 9/11 cover — the cartoonist Art Spiegelman and the magazine’s art editor, Françoise Mouly, in the former’s SoHo studio in 2003.Credit...Sara Krulwich/The New York Times

Li: The story of this is fantastic. I mean, to me, as a magazine maker, the fact that this went to press days later or something was extraordinary.

Remnick: The first idea was to do all black, and then Francoise and Art conspired on something much more interesting. And accomplished that in a very short period of time.

King: I went back and forth between this one and the Time one where the plane’s hitting the buildings: That still gives me goose bumps.

Rosler: This is about reaction, not about event.

Moss: Reaction is what it’s all about, right? A movement on the part of the editors to encapsulate — to make it make sense for readers.

Li: So what you’re saying is, an extraordinary image is not enough to be on this list?

Moss: My own brief was just, is it one of the all-time great covers? I’m making a distinction between a picture and a magazine cover because a magazine cover is, to me, an editor’s intervention.

8. Eliot Spitzer, New York, March 24, 2008

Credit...© Vox Media, LLC. Artwork: Barbara Kruger. Photo: Henry Leutwyler

When, in March 2008, New York governor Eliot Spitzer was unmasked as Client 9 in a prostitution scandal, Moss, then New York magazine’s editor in chief, scrapped the cover planned for the next issue. Jody Quon, who’s now the creative director of the magazine, reached out to a handful of artists and illustrators, soliciting concepts for a replacement. The winner was Barbara Kruger, whose early start in magazines — she was Mademoiselle’s head designer at 22 — informed her style as an artist: images overlaid with text, typically in red-and-white Futura Bold Italic, which probe truisms of power and gender. Kruger replied to Quon an hour later, amending a portrait of Spitzer (photographed by Henry Leutwyler) with two simple interventions: the word “BRAIN” and an arrow pointing at his crotch. As a Spitzer appointee said of the governor’s undoing in the accompanying story, “I don’t know that we need to overanalyze it. At its base it’s an old story.” — L.R.

Moss: We did a competition: He resigned on a Monday; we had to close the magazine on Thursday night. So we said to five artists and illustrators, make us a cover.

Remnick: This killed me, because I thought I had such a better one. Two magazines with competing dick jokes —

Moss: Once in a lifetime! I had nothing to do with this except to say yes to Barbara Kruger. She said to Jody, “Just give me a picture of Spitzer standing.” When Jody brought it into my office, I said, “OK, stop the competition.”

Li: As a cover, you couldn’t get more immediate.

Rosler: [Kruger] comes out of magazine design.

Moss: It’s not surprising she’s a great magazine-cover maker: She makes art out of the same text-image conversation.

9. Caitlyn Jenner, Vanity Fair, July 2015

Credit...Annie Leibovitz/Trunk Archive

Tabloids speculated endlessly over the changing appearance of Olympian turned reality dad Bruce Jenner in 2014. Tasteless as the coverage of Jenner’s lengthening hair, painted fingernails and shrinking Adam’s apple was, the physical transformation was undeniable, and yet the patriarch of the Kardashian-Jenners wouldn’t confirm anything publicly. By early 2015, there were rumblings of an imminent announcement: A docuseries was in the works, a Diane Sawyer sit-down arranged. But it turned out Jenner had also been secretly meeting with the Vanity Fair writer Buzz Bissinger for a profile. To prevent leaks, the magazine employed intense confidentiality measures, limiting knowledge of the project to eight staffers, isolating work on the story to one offline computer and hiring a security firm to guard Jenner’s Malibu home. The July cover — an Annie Leibovitz photograph of Jenner posed like a classic Hollywood pinup in a white satin corset, for which Lauren Bacall had served as a reference — had the simple headline “Call Me Caitlyn,” written by Vanity Fair’s editor in chief, Graydon Carter. With those three words, Jenner wrested back her narrative, became the face of a movement and ignited a groundbreaking discussion around gender identity. For many, Caitlyn was the first trans person they’d gotten to know. And Vanity Fair proved that not only could a century-old publication still deliver a scoop, it could also lead one of the biggest conversations of the era. — J.C.

Soller: We need to talk about influence more broadly. You think of the Caitlyn Jenner cover, which Gayle chose. That opened a conversation about gender in America that was simply not happening. That’s a different kind of influence than the influence you were talking about, Adam, which is about influence in the making of magazines.

Rosler: This is an incredibly successful cover, don’t get me wrong —

Moss: And degree of difficulty! I was reading about this cover in Graydon [Carter]’s book last night. They heard rumors that Jenner was transitioning and basically made a secret offer: Come out on the cover of Vanity Fair.

King: It was extraordinary at the time. To me, Demi Moore’s pregnancy was one of those, too.

Moss: Absolutely. [Jenner and Moore] are sort of in the same vein — a shocking image that crystallized a new idea, or reveled in one.

10. Demi Moore, Vanity Fair, August 1991

Credit...Annie Leibovitz/Trunk Archive

Demi Moore was pregnant with her second child when she and Leibovitz, at the end of a long portrait session in 1991, decided to try a few shots in the nude. Tina Brown, Vanity Fair’s editor in chief (who’d just had her second child) selected one of them for the magazine’s August cover, and Moore was thrilled. Fresh off the success of “Ghost” (1990), she didn’t anticipate the backlash. Several supermarket chains refused to stock the magazine, citing concerns over exposing “very young children” to the image of Moore, hands placed over her left breast and under her belly. The actress would soon be hit with criticism after criticism: for demanding a fair wage on her 1996 film “Striptease” (industry leaders dubbed her “Gimme Moore”); for her shaved head in “G.I. Jane” (1997); for her marriage to a younger man, the actor Ashton Kutcher, which prompted tabloids to scrutinize every inch of her for signs of cosmetic surgery. After many years of this, Moore’s Oscar nomination for the 2024 body-horror film “The Substance” felt like something of a vindication. As does the fact that, in the decades since this cover appeared, countless women, famous and not, have paid homage to Leibovitz’s image, whether in magazines or on social media. There’s no longer any question of whether a pregnant body can be seen as sexy — or seen at all. — M.S.

British press coverage of Demi Moore’s 1991 Vanity Fair cover.Credit...Clive Dix/Shutterstock

Soller: As someone who books a lot of covers — it’s so hard to get people to do anything these days. Like the idea that you could even get somebody to do this, or get Caitlyn to come out …

Rosler: It’s funny that all of the ones we’re talking about are women. These are about women and women’s rights. I’ll just leave that there.

King: You didn’t see pregnant women in the nude doing that [back then] —

Rosler: Pregnant women were always concealed, with their empire tops.

King: You weren’t trying to flaunt your baby bump, that’s for sure.

Remnick: That term is … so People magazine.

Soller: No one chose People magazine, which I thought was interesting.

King: I almost chose Mia [Farrow, in 1974], the first one.

Moss: It’s a new era of celebrity culture!

11. Yoko Ono and John Lennon, Rolling Stone, Jan. 22, 1981

Credit...Annie Leibovitz/Trunk Archive. Cover: © 1981 Penske Media Corporation

In the early afternoon of Dec. 8, 1980, Leibovitz, on assignment for Rolling Stone, visited John Lennon and Yoko Ono in their Upper West Side apartment’s sunny morning room. The ensuing photo shoot, as Lennon told Leibovitz after seeing some test Polaroids, “captured our relationship exactly.” Just hours later, Lennon would be killed by Mark David Chapman outside the couple’s building. So, when the Jan. 22, 1981 issue of the magazine was published, its cover portrait instantly became an elegy for the star — and the countercultural era he and the Beatles represented. It depicts Ono, fully clothed, lying on a white carpet with her nude husband curled up around her. Leibovitz intended the picture as a visual echo of the image of the couple kissing that had been used for the cover of Lennon and Ono’s album “Double Fantasy” (1980). And though Rolling Stone’s editor in chief, Jann Wenner, had originally wanted to feature Lennon alone, the musician had insisted on being photographed with his wife. Today, Leibovitz’s portrait endures as a testament to the musician’s singular devotion to Ono and a monument to the vulnerability inherent in any creative partnership. — J.D.

Moss: For its moment, this was a gigantic cover. Lennon had died, you know, a minute and a half before this. And the coincidence [was] that it was going to be on the cover anyway, because they had just released an album together. I worked at Rolling Stone at the time as a fact-checker, so I kind of remember that.

Remnick: Whatever became of Rolling Stone years later, Jann Wenner’s insight, which he deserves enormous credit for, is that the counterculture was the culture in the ’60s. And Lennon dying was the end of something. This image encapsulated that relationship [with Ono], which had special meaning if you were a Beatles fan: a kind of child nestling up to its maternal/lover figure. And then everybody was complicit in it: Leibovitz, the photographer; Lennon; Ono, who herself is a conceptual artist. It’s a very deliberate image. It was huge in the moment and hasn’t left many minds since.

Li: I’d also like to point out that there are no cover lines.

King: I bet they had cover lines before he died.

12. Madonna, Interview, June 1990

Credit...Herb Ritts/Trunk Archive. Cover: courtesy of Interview

The June 1990 cover of Interview landed in the middle of Madonna’s controversial Blond Ambition tour, capturing what was fast becoming her signature onstage move. The previous month, in Toronto, the pop artist had gotten a warning from local police: “If I touch my crotch during the show, I’m going to be arrested,” she was filmed telling her dancers backstage in her 1991 documentary, “Madonna: Truth or Dare,” defiant in her platinum ponytail and pointy Jean Paul Gaultier corset. (She went for it anyway, without consequence.) On the newsstands, that stereotypically macho gesture felt less transgressive, with Madonna, shot by Herb Ritts, playing a vintage cabaret performer in beaded false lashes and a clownish polka-dot bolero. The magazine added a slim red exclamation point after the singer’s name — emphasizing her shock value — and in the accompanying interview the star told the writer Glenn O’Brien, “I do think someone is protecting me. I don’t know if it’s an angel. It could be the Devil.” During another performance around that time, she told the crowd, “What’s the big deal? You can get upset when I try to grab your crotch. When I grab my crotch, it just means: ‘This is my space.’ ” — L.R.

Madonna, in her Jean Paul Gaultier cone corset, performing in Toronto in 1990 on her Blond Ambition tour.

Moss: I would separate out the fact that it was Madonna and look at [this cover] in the context of, “How do you do a superstar?”

Li: I just like the purity of this — at the height of Madonna’s powers, it’s pretty remarkable. I ended up having a lot of crotch-grabbers on my list. But I couldn’t ignore [the creative director] Fabien Baron’s Interview — I’m not sure how influential it is design-wise, but for me it’s absolutely one of the most memorable covers.

13. “Cosby: The Women; An Unwelcome Sisterhood,” New York, July 27-Aug. 9, 2015

Credit...© Vox Media, LLC. Photo: Amanda Demme

One after another, each woman, dressed in black, took a seat, placed her hands in her lap, and looked into the camera. It was the spring of 2015, two years before #MeToo took over Twitter, and Quon had hired Amanda Demme to shoot an extraordinary series of portraits. For decades, stories about Cosby drugging and assaulting women had circulated in the entertainment world, but the TV star, comedian and Jell-O spokesman’s power was so absolute that it was hard to envision they’d ever break through to the public. And yet after a short riff by the comic Hannibal Buress about Cosby’s history made the rounds on the internet, something shifted: Women were coming forward with harrowing accounts, and instead of other people ignoring or dismissing them, they were actually listening. Quon wanted a cover story that focused not on the famous assailant but on these women. It was an immense undertaking in terms of managing logistics and building trust, but 35 out of the 46 who’d spoken publicly agreed to participate, and the magazine soon scheduled shoots in Los Angeles, Las Vegas and New York. Demme had the idea of showing the subjects against a stark background, though it wasn’t until she, and later the art department, saw the portraits en masse that the final image came into being: a tableau of four rows with an empty chair at the very end — both a symbol of those not pictured and an acknowledgment that the reckoning had barely begun. — L.B.

The photographer Amanda Demme (in hat) on set with some of the 35 women who’d accused Bill Cosby of sexual assault and agreed to appear on the cover of New York.Credit...Courtesy of Amanda Demme

Remnick: I can tell you, as a magazine editor, [it’s incredible] to get all these people together and to accomplish this. And the strikingness and the multiplicity of the people; if it had been a Barry Blitt drawing, it would not have the same effect.

Moss: This was [all] Jody Quon, who is just amazing. You know, there was some conversation about Bill Cosby’s history, but Jody and the photographer, Amanda Demme, and a reporter, Noreen Malone, went and tracked down every woman who had allegations against Cosby and managed to convince 35 of them to pose for the cover.

King: But did you do it at one time or in pieces?

Moss: They did it in groups. To me, what’s so amazing about this cover — and what I love the most — is the empty chair, which represents the entire #MeToo movement that was to come.

Soller: How did that chair come about?

Moss: It came about for two reasons, one of which we should always talk about, which is the logistical: It evened out the line. Also, the photographer had the metaphor in mind.

Remnick: There are a lot of great New York magazine covers: There was the flood [and blackout, after Hurricane Sandy, in 2012], a simple helicopter photograph —

Soller: The Iwan Baan? That’s my favorite —

Remnick: And a lot of very funny things that New York has done over time, and even consumer-y things that have a certain flair. And I’m not saying this in a competitive sense, but I fell backward in my chair when I saw [the Cosby cover], because it encapsulated the moment and the crime and the outrage and the subsequent solidarity like nothing else I’d seen.

14. “View of the World From 9th Avenue,” The New Yorker, March 29, 1976

Credit...Saul Steinberg, “View of the World From 9th Avenue,” cover of The New Yorker, March 29, 1976 © The Saul Steinberg Foundation/Artists Rights Society (ARS), New York. Cover reprinted with permission of The New Yorker. All rights reserved

The 1970s were a good decade for New York City maps. In 1972, the Italian designer Massimo Vignelli and his associates distilled the jumble of subway routes into tidy colorful lines — an ordered landscape that didn’t always correspond to the reality above ground. Four years later, the Romanian-born American artist Saul Steinberg brought his imagined slice of Manhattan to the cover of The New Yorker. Like the Vignelli map, “View of the World From 9th Avenue” was all the more legible and beloved for its geographic inaccuracies. The hand-drawn scene looks west over a few fastidiously detailed city blocks. But after the Hudson River comes a nearly featureless expanse, save for a smattering of names (of airport hubs, cowboy states), a narrow strip of Pacific Ocean and distant doughy lumps (China, Japan, Russia). Here was Steinberg’s genius at work, zeroing in on a familiar phenomenon — in this case, New York’s collective myopia. “That was his goal,” said Mouly of Steinberg’s commissions for The New Yorker, which published its first drawing of his in 1941: “To make images so iconic that they live on in our brains as units of thoughts.” A contributor to the magazine for nearly six decades and a lodestar among subsequent generations of artists (the cartoonist and illustrator Liana Finck dubbed him “the winking philosopher”), Steinberg remains best known for his gently skewering “View,” reproductions of which have been hung on countless Manhattan walls — and lots of other places, too. — L.R.

The artist Saul Steinberg, photographed, with some of his drawings, by Neil Leifer in 1978.

Rosler: There’s the incredibly popular poster. Now you look at this and you go, “Eh, I don’t know.” You think, “What’s the point?”

Remnick: The point remains the point — about provincialism in New York. And it’s relevant to the recent elections.

Rosler: The ones we’ve chosen are reflective of the taste of today, which is about flatness.

Remnick: I would argue that Saul Steinberg, as a graphic artist — and I can say this, I promise you, apart from The New Yorker — is superior to anyone in what he was doing. In terms of drawing, his language is distinct. His style is lasting. There’s a craziness to it. It doesn’t feel dated. I wish he would be resurrected from the dead and start doing it all over again.

King: For me, though, guys, I like a cover that when you look at it, you know instantly what it says and what it means. I don’t want to have to translate, read or get an explanation. This one wouldn’t make my list.

Remnick: That’s like saying, though, “I wouldn’t want to look at Hieronymus Bosch.” You look at the detail and the little narrative interplays and that has immense meaning.

King: In a painting! But if I’m walking and just looking at the newsstand …

Moss: Well, The New Yorker, of course, doesn’t have to worry about that.

Remnick: By the way, neither does anybody else. Because these days the newsstand is nearly a memory.

Li: If we go back to the idea of influential, this really talks to me. It’s quintessentially The New Yorker. And it literally visualizes The New Yorker, all New Yorkers, as the center of the universe.

Moss: It’s practically a mission statement for the magazine.

15. “Aviation as Seen by Monkeys,” Fortune, January 1931

Credit...Neal Bose © 1931 Fortune Media IP Limited. Used with permission

In 1930, several months after the stock market crashed, Henry Luce launched Fortune. It was hardly an auspicious moment for a lush new magazine devoted to the machinations of American corporations, but the media magnate insisted there was a ready audience. Until then, business publications had been trade journals filled with dry statistics. Luce, who’d co-founded Time seven years earlier, understood that the movement of capital was of great interest to those moving it — and that a magazine itself could be a status object. Some 30,000 people subscribed to the inaugural 184-page issue, all willing to pay a dollar (nearly $20 today) per issue. Here was a publication about money that itself felt like money, with its thick paper stock, grand proportions (11 by 14 inches) and vibrant illustrated covers commissioned from artists (Antonio Petruccelli, Ervine Metzl) and displaying railroads, smokestacks, steamships and other emblems of enterprise with glorious creativity. In Neal Bose’s January 1931 cover, a classic example of the magazine’s sensibility, a troupe of monkeys scramble to catch a glimpse of a then-novel phenomenon: an airplane soaring overhead. As the years passed, styles changed, but Fortune held onto its aesthetic mission: In July 1965, Walter Allner, the publication’s Bauhaus-trained art director, designed the first magazine cover using computer graphics. Its depiction of ascending arrows was less whimsical than the monkeys, but the image nonetheless conveyed energy and delight — a far cry from the cold graphics and interchangeable portraits of CEOs and other power players that peer out from most business publications today. — L.B.

Henry Luce reading the May 1938 issue of Fortune, a magazine he launched in 1930.

Rosler: The Fortune cover [Adam] chose was fabulous.

Remnick: And their format was the size of a bedsheet.

Moss: When you find them in a flea market or something, they’re so satisfying. The [1930s] era of the magazine was just a sequence of fantastic covers. This one is very clever — aviation must’ve seemed so peculiar at the time.

King: But, Adam, without cover lines, I don’t know what I’m looking at or what it means.

Moss: I’ve looked through every one of the early Fortune covers, and they’re just delightful, most illustrating an industry, some new, some in transition. They’re so radically different from what Fortune covers became, what all covers — except, in a sense, The New Yorker — became.

16. Marilyn Monroe, Avant Garde, March 1968

Credit...The Last Sitting ® 1962 © Bert Stern Trust. Cover: courtesy of The Herb Lubalin Study Center at The Cooper Union

When the American photographer Bert Stern and Marilyn Monroe met in the summer of 1962 for a Vogue feature, he was more interested in the woman than in the clothes. A suite at Hollywood’s Hotel Bel-Air served as the set, and he brought along a suitcase full of necklaces and scarves — accessories that suggested easygoing spontaneity when compared to the magazine’s chosen dresses and furs. (A second day of shooting with some of those items followed.) The resulting portraits were luminous and unguarded, rare qualities (back then and especially now) when it came to celebrity subjects. Monroe reviewed a number of the contact sheets, striking out frames with an orange X, though she died by overdose before the issue was published. The roughly 2,500 photos from “The Last Sitting” defined Stern’s career but left him unsatisfied: “They never quite communicated the dazzling image of Marilyn that existed in my mind’s eye,” he explained in a 1968 issue of Avant Garde, a short-lived magazine edited and published by Ralph Ginzburg in collaboration with the designer Herb Lubalin. (The latter’s slanted logo gave rise to a typeface of the same name.) A forerunner to zine culture and art-book publishing, Avant Garde offered Stern another chance to get it right by running “The Marilyn Monroe Trip,” a collection of experimental, acid-colored serigraphs, based on his original images, that brought the screen star into the pop-psychedelic era. By contrast, the cover struck an unassuming note, with kraft-style paper in lieu of the usual glossy stock and a palette of umber tones informed by the Southern California landscape: Marilyn Monroe, a natural beauty at last finding her light. — L.R.

An interior spread from the March 1968 issue of Avant Garde, for which Stern turned pictures from “The Last Sitting” that he’d originally shot for Vogue into acid-colored serigraphs.Credit...The Last Sitting ® 1962 © Bert Stern Trust. Photo: courtesy of The Herb Lubalin Study Center at The Cooper Union

Li: In terms of the art of magazine-making, this is an important cover. The silk screen of Marilyn on kraft paper is by my favorite designer, the legendary designer and magazine maker Herb Lubalin. It’s a very short-lived publication [just 14 issues between 1968 and 1971]. They probably spent all their money on this cover.

Moss: I agree — beautiful.

17. Produce, Gourmet, May 1969

Credit...Ronny Jaques/Gourmet © Condé Nast

Gourmet, the self-described magazine of good living, was established in 1941, a time when Americans would soon be forced to ration staples like sugar and coffee, and few were fussing over haute cuisine. That didn’t stop the founder and publishing veteran Earle MacAusland from selling his vision of food as fantasy, which, in the midst of wartime deprivation, clearly appealed to readers. By the early ’60s, the magazine, under the eye of its executive editor Jane Montant, had distinguished itself with its rich photography and focus on travel, both of which come to life on the magazine’s May 1969 cover. Shot by the British photographer Ronny Jaques, it shows a stone ledge running along a sky-scrimmed reflecting pool — part of the 1,900-year-old remains of the Roman emperor Hadrian’s villa complex near Tivoli — lain with immaculate produce, from crisp green beans to bright red tomatoes to Rosa Bianca eggplants, all of which gleam like mythological spoils. The setting was Italy, but the style recalled that of the Dutch masters. Along with the rest of the issue, which included writing by the chef and author James Beard, the cover helped create an era — one we’re still in, as a quick scroll will attest — where food was serious, seductive and a marker of status. — M.M.

Li: This is a whole category that we here at T love, the adulation and the still life of beautiful living and food. And this is such an improbable picture of produce among the ancient ruins, clearly styled to perfection. It’s just a great synthesis of the purpose of Gourmet magazine.

Soller: Also, Instagram wouldn’t exist without this. The idea of the veneration of food.

King: I always thought Martha Stewart had the best covers in the home entertaining space.

Li: Well, this is just so much earlier, right?

Rosler: And this is for the aspiration and consumption of luxury: It’s a worthy subject at a time when that was a relatively new idea.

18. “Planet or Plastic?,” National Geographic, June 2018

The image inside the iconic yellow frame is simple and familiar — an iceberg rising out of the ocean — but then comes the chilling double take: This is actually a gargantuan plastic bag. The Mexican artist Jorge Gamboa first created the photo illustration in 2017 for a group show at a Mexican college; later that year, it won a prize at a Bolivian design biennial. Afterward, National Geographic published it on its cover to mark the launch of its #planetorplastic campaign to reduce single-use plastic. Within a day of Vaughn Wallace, the magazine’s photo editor, sharing the cover on Twitter, it had gone viral. The clever optical illusion also delivers a primal shock: This could be a still from a horror movie, one in which an ordinary plastic bag has taken on monstrous force — a mutant of our own making. In 2018, when Gamboa’s “Iceberg Plástico” was published, the magazine reported that 18 billion pounds of plastic were entering the world’s oceans per year. Today, the global conservancy group Oceana estimates that figure to be 33 billion. — L.B.

The Mexican artist Jorge Gamboa’s process shots of plastic bags for his photo illustration “Plastic Iceberg,” which previously appeared at the 2017 Bolivian Biennial poster competition.Credit...Jorge Gamboa

Rosler: There was one [National Geographic cover] that I thought all of us would pick, and therefore I didn’t: The Afghan girl with the green eyes [from 1985].

Moss: I like this better, though: It’s conceptual.

King: This one makes you think; I’d never seen it.

19. Sheryl Lee, Lara Flynn Boyle and Peggy Lipton, TV Guide, Sept. 8-14, 1990

Credit...TV Guide/Everett Collection

In 1990, the most-watched shows on television were “Roseanne,” “The Cosby Show” and “Cheers.” With the surreal, operatic “Twin Peaks,” which premiered that April and combined neo-noir and psychological horror, the director David Lynch, along with co-creator Mark Frost, forever transformed a TV landscape awash in sentiment and moralizing. And while the show never quite achieved mass popularity (after 36 million people watched the two-hour premiere, its ratings faltered), it had its claim on the culture. When three of the show’s female stars appeared on the digest-size cover of TV Guide on the eve of its second season in September 1990 — in a stacked, slightly gauzy composition photographed by Mario Casilli that nodded to the homecoming queen portrait of Laura Palmer that appears in the show — it was the ultimate expression of the experimental crossing over into the mainstream. At the time, TV Guide had the third-largest circulation of any publication in the country (with 15.8 million readers in the first half of that year), and this magazine of channel listings had created something beautiful, poignant and weird: Lynchian, in other words. Now, the cover also harks back to a time when watching just about anything was a more collective experience, and one very much buoyed by print, whether TV Guide or its glossier counterparts. The next month, the women of “Twin Peaks” made the cover of Rolling Stone. — J.C.

Li: This, to me, is this synthesis of transgression and normalcy. This idea of David Lynch’s “Twin Peaks” characters on the cover of the most mass magazine out there. How weird and how perfect.

Remnick: Was “Twin Peaks” a big ratings success?

Moss: For an ambitious, arty show, it was.

King: It wasn’t fringe! People loved “Twin Peaks.” That [1991] finale, people went nuts to see it.

Moss: For a person who just loves all kinds of magazines, it’s gratifying to see TV Guide on this list.

20. Michaela Bercu, Vogue, November 1988

Credit...Peter Lindbergh, courtesy of the Peter Lindbergh Foundation, Paris. Cover: © Conde Nast

For 17 years, Grace Mirabella ruled Vogue as editor in chief, and her covers dependably featured a big-haired, big-eyed model with a Mona Lisa expression and cheeks only slightly less painted than her lips, carefully framed on a white studio background and often shot by Richard Avedon. When Anna Wintour, who replaced Mirabella in the summer of 1988, debuted her first issue in November, she obliterated her predecessor’s visual legacy with a single image. Gone were the famous heroines (Isabella Rossellini, Paulina Porizkova), and in their place was the 18-year-old Israeli model Michaela Bercu, her spontaneous smile so wide she looked like she was squinting, her wavy blond hair swept across her neck, because the Peter Lindbergh photo had been taken outside. The details have become fashion lore — that Bercu, as styled by Carlyne Cerf de Dudzeele, wore stonewashed $50 Guess jeans with a $10,000 haute couture bejeweled Christian Lacroix jacket because the piece’s matching skirt didn’t fit; that Wintour’s cover presaged “high-low” long before Karl Lagerfeld for H&M; that the magazine’s printers called Vogue to ensure the cover wasn’t a mistake. It wasn’t. And the breezy, relatable image, which so firmly set the standard it now appears unremarkable, sent a clear message that a new reign had begun. — J.C.

Anna Wintour at the opening of a Metropolitan Museum of Art’s Costume exhibit in 1988, her first as Vogue’s editor in chief.

Remnick: Anna Wintour’s first Vogue cover …

Li: That declaration of high and low. This was an influence … is an influence.

King: Because I just look at it and I go, “OK, 1988.” Is the model a name we know?

Li: Not really.

Soller: And we can’t avoid the elephant in the room …

King: Anna?

Soller: She still works there — her influence.

Moss: If it really was such a great departure, which I didn’t know, that’s amazing. You’ve convinced me.

King: But if it wasn’t Anna Wintour’s first cover, would we pick it?

Remnick: It graphically broke away from the kind of highly stylized society —

Rosler: She’s smiling —

Remnick: She’s wearing jeans.

21. “Boy With Baby Carriage,” The Saturday Evening Post, May 20, 1916

Credit...The Saturday Evening Post and cover illustration licensed by Curtis Licensing

Norman Rockwell’s first cover illustration for The Saturday Evening Post, “Boy With Baby Carriage,” depicts a stern boy dressed up in dapper attire pushing a pram past two other boys in baseball uniforms. One of the players tips his hat, flaunting his leisure, while the other looks on, gaptoothed and amused. Previous Post covers often featured idealized portraits of women at leisure in sterile poses easily mistaken for advertisements. This one showed the dynamic friction of urban life in the United States, injecting an element of narrative realism into the magazine’s style. Rockwell biographer Deborah Solomon ranked it among the artist’s most “psychologically intense” works. Look again at the faces: The boy pushing the carriage is weighed down by his responsibilities; the jeering kids, meanwhile, aren’t necessarily bullies. The illustrator, who was 22 when he sold the image to the Post, went on to produce hundreds of their covers, which all told a story while straddling the line between everyday life and nostalgia. (Think of the bare-bottomed young patient inspecting his local doctor’s framed credentials in 1958’s “Before the Shot”). But “Boy With Baby Carriage” set the Rockwellian tone, evolving the look of magazines and, arguably, America’s imagination of itself. — J.D.

The illustrator Norman Rockwell with his frequent model Billy Payne, who informed the look of all three boys depicted on the May 20, 1916, cover of The Saturday Evening Post.Credit...Courtesy of the Norman Rockwell Museum Collection, Stockbridge, Mass.

Remnick: It’s interesting. We now publish Kadir Nelson, a Black artist who celebrates and explores Black life and history in ways that remind me of Norman Rockwell to some degree. And we really should represent Rockwell — his imprint on magazine covers, which is obviously before our time, lasted for 40 or 50 years.

King: That’s not my favorite cover, but I like anything Norman Rockwell.

Remnick: The classic is the Thanksgiving one [from 1943], which gets played with a lot.

King: But this one’s his first. I like that.

22. Reverend Dr. Martin Luther King Jr., Ebony, May 1968

Credit...Ebony © 1968 1145 Holdings LLC. All rights reserved

Founded by the businessman John H. Johnson in 1945, Ebony would become one of the most popular magazines among Black Americans, long ignored or maligned by other national publications. Given this, the magazine’s initial aim of showing “the positive everyday achievements from Harlem to Hollywood” was political in its own way, but beginning with the Civil Rights Movement, it increasingly covered history and politics head-on. After the Reverend Dr. Martin Luther King Jr. was assassinated on April 4, 1968, Time didn’t put him on its cover. Life did, but only afforded him seven of its 100-plus pages. And The Atlantic, a magazine founded by abolitionists, hardly mentioned his passing. Ebony, by contrast, chose a spare photo of King, his hand under his chin, for its May 1968 cover. The picture had been taken by Moneta Sleet Jr., a longtime staff photographer whom Coretta Scott King reportedly requested document her husband’s funeral. (Sleet’s picture of the widow holding her daughter during the service won him a Pulitzer Prize.) Inside the issue, the magazine ran two features on King and included the conclusion to the prescient “I’ve Been to the Mountaintop” speech he’d delivered the night before his death — “I may not get there with you. But I want you to know tonight, that we, as a people, will get to the Promised Land!” — turning Ebony’s pages into an instrument of mourning, a memento that kept his image and final words alive. — M.M.

John H. Johnson, left, Ebony’s publisher and editor, and Ben Burns, its executive editor, at the magazine’s Chicago office in 1946.Credit...© Wayne Miller/Magnum Photos

Remnick: [It comes up] anytime Ebony is discussed — it’s a pretty classical cover. It might not be the greatest, but its timing was …

King: It is iconic.

Remnick: Life magazine was, for the midcentury, the magazine of imagery. It was the magazine that every middle-class American would get. But there were other formations of it, obviously: Ebony and Time magazine also held central places in the imaginations of their readers.

23. Brandi Chastain, Sports Illustrated, July 19, 1999

Credit...Robert Beck/Sports Illustrated

When the U.S. faced China in a packed Rose Bowl stadium for the final match of the 1999 Women’s World Cup, mainstream media was starting to grasp that there was a growing and enthusiastic audience for women’s sports. An estimated 40 million people were watching the television broadcast, and the photographer Robert Beck was in the stadium to take pictures for Sports Illustrated of the crowd, which included President Bill Clinton in a V.I.P. box. After the goalless game went into overtime and then a penalty shootout, Beck, despite not having credentials to be on the field, slipped through the stands to get a closer vantage point just as the shooters were lining up. It was a 4-4 tie when Brandi Chastain’s shot sailed past the goalkeeper Gao Hong and into the net. The crowd exploded and an ecstatic Chastain ripped off her shirt, displayed her sports bra and dropped to her knees. That’s when Beck took his shot. Certainly, in the era of lad mags, readers were used to looking at barely clothed women. This, though, was a complete departure from the usual commodified female form: Chastain had taken her shirt off to celebrate. Plenty of soccer players had done the same before her, except they weren’t women. So not only did Beck’s photo capture an astonishing moment in women’s sports — it offered a generation of young girls seeing Sports Illustrated a new vision of themselves. — L.B.

King: I like the bliss, the joy, the fact that she took off her top.

Remnick: We’re light on Sports Illustrated. There was a period where Neil Leifer and a couple of sports photographers took astonishing boxing photographs.

King: Where you can see the sweat coming off their faces.

Remnick: I think it’s great to have women in sports, too, on this list.

King: You just don’t know if this is the right one?

Remnick: The Sports Illustrated ones I’m going to think of are very male, to be honest with you.

King: That’s what I think is fun about this.

Remnick: Sure, and this was an iconic sports moment.

24. “Women in Revolt,” Newsweek, March 23, 1970

Credit...Courtesy of Newsweek

Newsweek harnessed the force of the women’s lib movement with this March 1970 cover, featuring a photo-illustration of a woman tinged in revolution-red, her raised fist busting through the ring of the female gender symbol, an ancient astrological symbol for Venus popularized by the Swedish botanist Carl Linnaeus in the 18th century to help him differentiate between male and female plants. Above it was the line “Women in Revolt,” a characterization that, as it turned out, also applied to the Newsweek staff. On the day the issue was released, 46 female employees, having held covert meetings in the office bathroom and at a nearby restaurant called the Women’s Exchange before seeking the help of the lawyer Eleanor Holmes Norton, announced that they were filing a lawsuit against the magazine for gender discrimination. In those days, women at the magazine were secretaries, fact-checkers or mail girls (Nora Ephron had been one for the editor in chief Osborn Elliott in 1962) while men were writers and editors. In an exception that proved the rule, the “Women in Revolt” cover story had been written by a woman, Helen Dudar, though she wasn’t a staffer but a freelancer — and the wife of a Newsweek editor. The cover, then, was immediately linked to an instance of feminism in action. And in addition to changing things at Newsweek — Lynn Povich, who went on to write a book, “The Good Girls Revolt” (2013), about the case, was named its first female senior editor in 1975 — the suit precipitated similar ones against Time Inc., Reader’s Digest, The New York Times and other press outlets. — J.C.

The lawyer Eleanor Holmes Norton (at table second from right) and some of the Newsweek employees she was representing at the 1970 press conference at which they announced their lawsuit against the magazine for sex discrimination.Credit...Barton Silverman/The New York Times

Remnick: Ms. magazine had a number of good covers, particularly early on. The first one [in 1972], with the [woman resembling a] multi-armed Hindu goddess, is very memorable to me, but now that might be an image that’s overused.

Rosler: I like [the Newsweek image] better actually.

Remnick: And it was 1970, two years before Ms. started.

Rosler: And it’s important.

Soller: Because of the lawsuit …

Moss: I just think it’s more successful.

25. “The Doe Eye,” Vogue, January 1950

In the 1930s, Vogue moved away from illustrated covers, eventually adopting its now-familiar formula: a photograph of a model or celebrity (or several) layered over or under the slender serifs of the publication’s nameplate. But for its January 1950 issue, Alexander Liberman, Vogue’s art director and an accomplished multidisciplinary artist in his own right — he loved Modernism — oversaw an image by Erwin Blumenfeld that reduced the face of the supermodel Jean Patchett to its most minimal. A shadowed green eye, an arched eyebrow, cherry-red lips and a birthmark were made to float over a white void in an abstraction of the so-called doe-eyed look. Before emigrating to New York to escape World War II, the German-born Blumenfeld had spent his formative years in Amsterdam, where he threw himself into the Dada movement, making drawings, photographs and collages that combined political commentary with a humorous approach to the human form. In one 1932 work, he cut the eyes, mouth and nose from a black-and-white photo of a woman and shifted them around the frame. With his Vogue cover, produced almost two decades later, he took that idea (moving Patchett’s birthmark from the upper right to the lower left side of her face) and made it feel fresh, opening new possibilities for fashion photography experimentation. — M.S.

The photographer Erwin Blumenfeld’s image of Jean Patchett before he obscured much of her face for Vogue’s January 1950 cover.Credit...© The Estate of Erwin Blumenfeld 2025

Moss: I looked at old Vogues and Harper’s Bazaars and threw some in because I thought we should be talking about fashion covers, because they’re so crucial to the magazine medium.

Soller: So are we going to include this one?

Moss: I vote for the [1940] Vogue bathing suit one.

King: Me too.

Li: For me, the Blumenfeld.

Rosler: Yeah, this is timeless.

Moss: Martha thinks this is timeless — all right.

Kurt Soller is the deputy editor of T Magazine.