The Playboy Funnies: Hefner Editing Feiffer

By Paul MortonFebruary 1, 2018

The Playboy Funnies: Hefner Editing Feiffer
ON APRIL 16, 1958, Hugh Hefner wrote a letter from his Playboy offices in Chicago to the cartoonist Jules Feiffer in New York, care of the McGraw-Hill Book Company. Hefner liked Sick, Sick, Sick, a collection of cartoons from Feiffer’s Village Voice strip. He had also read Feiffer’s short story “Passionella,” a satire of celebrity culture, finding it “a really extraordinary modern-day fairy tale.” “Passionella” had originally appeared in the digest Pageant, where it had been advertised as a “comic book for adults.” That phrase, it turns out, is older than we think.

At the time Feiffer was in his late 20s, and still developing his voice. His line was neurotic. His characters had weight, but even when they stood in place they could never stay still. Their shoulders would straighten and then slump a centimeter or two from one panel to the next. He employed a child’s scrawl to represent the grown-up’s id. Feiffer’s strip could be politically charged — he loved to attack middle-of-the-road liberals — but it also indicted the Voice’s hip readers who indulged new sexual mores in order to achieve a facile identity and something adjacent to pleasure. Hefner saw a kinship. “I think much of what you have been doing for The Village Voice is exactly right for us and with even more emphasis on urban living as apart from strictly Village living, work done specifically for us could be a very exciting addition to PLAYBOY,” he wrote.

Hefner gave more details in a subsequent letter. He wanted Feiffer to focus on the same subjects Playboy foregrounded:

the man and his job, his relationship with his boss and associates, the organization man, getting ahead in the world, male and female fashion, dining and drinking, sports cars, hi-fi, jazz, the Beat Generation, psychoanalysis, advertising, MR, the movies, television--all of these are fine subjects for us.

Hefner clarified his wishes in a letter he later sent to Ted Riley, Feiffer’s agent:

These people are not very different from the ones he’s been placing under the microscope so far--their clothes are just a little neater, their shoulders a little more natural--the girls wear sack dresses instead of Chinese earrings and sandals. But they are as sick as anyone in the Village and just as ripe for satire--maybe a little sicker and a little riper.

Hefner, himself an aspiring cartoonist in his youth, had wanted to make Playboy a showcase for cartooning talent comparable to The New Yorker. Still, Feiffer’s work didn’t fit with that of other artists Hefner was recruiting at the time. A typical Playboy cartoon featured an unattractive male and a cartoon version of a Playboy model. If the reader recognized himself, he recognized his imperfect body. On the one hand, the cartoons poked fun at the reader’s low physical status. On the other, they indulged his fantasies, his belief that beautiful women were a right to enjoy as much as good food, books, and music. The magazine’s bullpen in the late 1950s included Jack Cole, most famous as the creator of Plastic Man, and the Mad genius Harvey Kurtzman. Cole and Kurtzman’s lusciously colored cartoons for Playboy indulged their adolescent souls. Their work had little in common with Feiffer’s black-and-white sequential narratives, energetic dialogues, and twisting monologues.

From Hefner’s letters, it seems Feiffer was a hard get. The magazine celebrated a materialist, swinging culture that divorced aesthetics from morality. Feiffer’s work did not. Hefner assured Riley that Feiffer would not have to change his point of view. He only asked that Feiffer agree to not publish at any magazine that could be considered a Playboy competitor. He could keep his strip in the Voice. Feiffer agreed.

The collaboration proved fruitful. Through the end of the 1960s, Playboy would publish dozens of Feiffer’s cartoons, some as short as a page and others stretching to the length of a comic book. Playboy would also publish Feiffer’s prose, including the novel Harry, the Rat with Women, and The Great Comic Book Heroes. The following exchange comes from a 2009 interview I conducted with Feiffer:

[Y]ou were so against everything that Hugh Hefner stood for in that magazine.

Well, apparently. But Hefner was terrific about it. [He didn’t] try to shape me to the demands of his publication as every publication except for the Voice generally did. Whether you were working for Esquire or Harper’s or the Atlantic or The New Yorker they wanted you to be like them, with their sensibility. Hefner, when he sent me back notes, he sent me back richly-detailed notes, panel-by-panel breakdowns of what he liked and what he didn’t like. And it was never to change my point-of-view to his or to the magazine’s. But it was to make my argument stronger by strengthening what he thought was a weakness. And in many cases he was right. 

Do you remember any particular case where he was right?

No, I can’t, but when he was wrong he let me have my way. Or when I thought he was wrong.

Feiffer admiringly quotes a few of Hefner’s early letters in his 2010 memoir, Backing Into Forward. I recently read the entirety of Hefner’s letters to Feiffer, at least the ones that still exist, which are held in three folders with Feiffer’s papers at the Library of Congress. The correspondence begins in 1958 and lasts until 1990, but begins to taper off in the early 1970s. The Hefner of the Feiffer letters — unlike the pompous, pseudo-intellectual bore of “The Playboy Philosophy,” his column which ran in the pages of the magazine through the early 1960s — is lovable and intelligent. He writes Feiffer a moving remembrance of Jack Cole after Cole’s suicide. The letter shows a striking familiarity with the cruelty of the business side of comics, and the terrible pressures of syndication. (This was not long before Feiffer’s own strip would be syndicated.) Hefner grows excited when he learns about Feiffer’s work on Will Eisner’s The Spirit and reveals himself to have been a fan of the comics in his youth. He gets angry at Feiffer for publishing with two Playboy competitors, Ivy Magazine and Madison Avenue, only to be reassured that Feiffer had sold stories to these magazines prior to his arrangement with Playboy. And Hefner jokes about the vast gulf between his and Feiffer’s lifestyles. The affection between the two men, or at least Hefner’s for Feiffer, seems genuine.

As an editor, Hefner focused primarily on diction, dialogue, and narrative. But he also subjected Feiffer’s work to the same preternatural vision that would lead him to reject a photograph of a slightly cross-eyed Playmate. He compliments the “fine variety” with which a character in one of Feiffer’s strips holds his hands while interacting with a woman, and then suggests that in the second to last panel, the man only place one hand on the woman’s shoulder so that it doesn’t appear that he is strangling her. He follows this with, “I hope you can hold the subtle charm of the facial expressions, the reaction and inter-reaction in your finish that you have in this rough.” In the same letter, he encourages Feiffer to maintain his habit of handwriting his own dialogue rather than reverting to type. “[E]ach page by you is something special that draws the reader in. Both words and drawing associate directly and are clearly parts of a consistent, engaging whole.”


On August 1, 1962, Hefner wrote a nine-page letter on a draft of “The Lonely Machine,” one of Feiffer’s masterpieces which would be published in the December 1962 issue of Playboy. (“The Lonely Machine,” unlike most of Feiffer’s Playboy stories, is currently in print in the Fantagraphics collection Passionella and Other Stories.) I could not locate the original drafts Feiffer sent Hefner, but it’s clear from reading the letters alongside the final versions of the cartoons as they appear in the magazine that Feiffer listened to Hefner more often than not. “The Lonely Machine” thus offers an example of two disparate philosophies coalescing in Playboy’s pages.

I’ll begin by summarizing “The Lonely Machine” as it appeared in the magazine.

A lonely man named Walter Fay has been unlucky in his attempts to develop meaningful relationships throughout his life. “By myself I get along fine — but put me in a room with one other person — I become only half of me,” he says. “Put me in a room with two other people – I’m a tenth of me. Put me in a room with a mob and I’m nobody!” He goes to parties even though he tells himself there’s no reason to go. In one set of three panels he calls a girl a “castrator,” a boss a “fascist,” and his family members “sickies.” The problem isn’t him. “If only not being alone didn’t depend on other people,” he says. One day he builds himself a robot, called the Lonely Machine, which provides him with the kinds of relationships he wants. The machine is programmed to respond in stereotypical ways to what one would expect from a mother (“When you’re in trouble who’s the only one you can turn to?”), a father (“Are you sure you’ve made a wise decision, my Walter?”), or a lover (“Machines can’t afford much but you, Walter, deserve the best,” it says after giving Walter dandelions). One day, Walter decides to go out in the world again, with a newfound confidence.

The machine feels neglected and humiliated by this new treatment. “Walter, what was my crime? What was my terrible crime?” It descends into alcoholism. Walter takes a new lover and banishes the machine to the basement. A tossed-off love/sex object, it finds a new, empty life as a dressmaker’s dummy for Walter’s new lover.

Hefner begins his letter about the “The Lonely Machine” by summarizing what he feels is the point of the story. A man who has always been failed by people builds a machine so that he can create a creature without “human imperfection.” Walter gains security “through the constant attention, love and loyalty of the machine.” The fault, of course, isn’t the world’s as much as Walter’s, and once he gets the “inner security” he needs, he can go out into society, “capable of loving and being loved.” Hefner concludes, “[H]is need for the machine — which had supplied all the emotional things he should have received as a child, and didn’t, is at last ended.”

“Told in this direct manner, it is quite warm and charming, and easily understood,” Hefner wrote.

Feiffer was capable of depicting warm and charming stories, and Hefner was correct to call “Passionella” a fairy tale. But “The Lonely Machine” is as savage as any of Feiffer’s plays, novels, or essays. Hefner’s summary misses the tragedy of the Lonely Machine’s fate. Whether intentional or not, “The Lonely Machine” is part of a tradition of science-fiction stories riffing on the Turing Test. Does the Lonely Machine think? Is this machine, which bears no clear gender, human, perhaps even more human than Walter himself? In the final long horizontal panel, divided between Walter walking off with his lover on the left side and the machine standing alone on the right, the narrator says, “Walter Fay never felt disappointed, ignored, rejected or betrayed — or any other feeling again.” Whether the machine feels emotion remains ambiguous in Feiffer’s spacing and pen line. Is the machine miserable, banished to a life without love, or has it instead given up all human emotions, including pain?

Nonetheless, Hefner is on to something with his major criticism of the story. In the original draft, Walter Fay has a failed relationship with a woman before he builds the Lonely Machine. Hefner explains why Feiffer needs to remove this turn in the story.

A woman is only capable of giving a man one kind of love and attention, whereas the machine presumably is able to somehow give him those things that he missed in childhood — mother love and father love, as well as the love of a sweetheart — which fills the void of his early years, as no sweetheart could.

By introducing a romantic relationship early on, Feiffer would be muddying the conflicting urges in Walter’s psychodrama.

But Hefner also thought that introducing a relationship before the Lonely Machine appears would make no sense for another reason. The failure of an early relationship, as opposed to the absence of a relationship, would have taught Walter a very different lesson: not that he needed to create something that gave him the feelings a relationship imparts, but that he should avoid relationships altogether. Hefner suggests a different science-fictional image that would follow such a turn in events: “[H]e might much more logically be expected to crawl into a tiny cubicle, in which all walls and ceiling were covered with mirrors, and hooked up with a p.a. system, that would permit him to talk to himself, and then answer, and thus be wholly self-involved.” This image, we might suspect, would awaken the Playboy reader’s fear that he is nothing more than a masturbator.

Whether or not Feiffer agreed with Hefner’s reasoning, he agreed with his publisher’s conclusion. The final version of the story does not include this plot element. In the original draft, similarly, there was no explanation of how Walter created the Lonely Machine. Hefner suggested giving Walter a basement workshop, as it is something a man would be likely to have. Feiffer followed his advice.

But Feiffer did not take all of Hefner’s suggestions. Hefner was not crazy, for instance, about Walter receiving dandelions from the machine, thinking they would not be the kind of gift a man would want. Instead, he suggests a scene showing Walter and the machine in bed together. The machine would tell Walter, “You’re the best, Walter … you’re the best I’ve ever had.” The panel, for Hefner, would offer a good contrast to a later gag in the story, in which Walter, after he regains his confidence, actually has sex with a woman. His new lover tells him: “Oh, Walter — you hurt me.” The moment satisfies Walter’s ego. “Did I really?” he smiles. Though Hefner doesn’t delve too far into this possibility, these parallel scenes would have added a different dimension to the story: Walter’s relationship with the machine sets him up with all the imagined norms of a heterosexual relationship, which in turn prepares him to experience a male-female relationship while remaining oblivious to complicated realities. Feiffer, however, kept the dandelions, making the story as much about gender as it is about sex. In Feiffer’s version, the machine’s ability to switch between genders allows Walter to escape the trap of masculinity, to be the kind of man who can enjoy dandelions without fearing society’s condemnation.

In any case, Feiffer wrote and drew a new draft and sent it to Hefner. On August 21, Hefner wrote back: “I’m very pleased with the way it worked out, dandelions and all.”


Hefner understood a lot about the male ego, but his letter to Feiffer is oblivious to the concept of gender performance. That’s surprising, given that Hefner, among his other attributes, was a genius camp performer. 

Hefner attempted to keep Playboy’s erotica classy. He presented himself, in his column and on his television show, as an autodidact, a renaissance man fascinated by pop philosophy, jazz music, and the contemporary arts. And yet his analysis of “The Lonely Machine” still holds fast to the ideas that all men have basement workshops and can’t enjoy dandelions. His notes on the story suggest that Feiffer’s cartoons and those of Playboy’s other cartoonists, which to a lay reader seem so oddly placed next to each other, may not have been so different in Hefner’s eyes. “The Lonely Machine,” like the magazine’s other cartoons, is about a small man achieving the status of a Playboy.

And what of Feiffer’s decision to accept Hefner’s criticism and cut the protagonist’s earlier relationship with a woman? “The Lonely Machine” would have been a very different story with that plot element, but not necessarily a worse one. If anything, it would have been more savage. Walter would have been a little closer to Huey, the man-on-the-make of Feiffer’s strips — or to Jack Nicholson’s Jonathan, the evil-eyed, self-loathing lothario of Mike Nichols’s Carnal Knowledge, for which Feiffer wrote the screenplay.

Walter would not, as Hefner hypothesized, have locked himself in a room in a state of complete self-absorption. Rather, “Woman” would have become a symbol in itself, something capable of being repeated, ad infinitum. The ending of “The Lonely Machine” would have been more open-ended. We could imagine a future for Walter in which he leaves his new lover, returns to the Lonely Machine or builds another one, returns again to a human woman, and again to the machine. The story would thus have been a prescient science-fiction anticipation of online dating.

But this version of the story might also have hit a little too close to describing Hefner himself and what he was and was coming to stand for in American culture — a figure who could be warm, charming, and self-aware; a liberal champion of civil rights, gay rights, the First Amendment, and abortion rights; and the leader of a secular faith that demeaned half the human race.

The Walter Fay at the end of this earlier version of “The Lonely Machine” has something in common with Cliff Robertson’s portrayal of Hefner in Bob Fosse’s 1983 film Star 80. Fosse’s film is a biopic about Dorothy Stratten, the Playboy model who was brutally murdered by her estranged husband. Robertson’s Hefner is charming. But he is also a little too cool and self-assured, blessed with a perfect eye, carefully studying photograph after photograph of his models, each of them a lonely machine.


Paul Morton is a PhD candidate in the Department of Comparative Literature, Cinema and Media at the University of Washington. He is writing a dissertation on the Zagreb School of Animation.

LARB Contributor

Paul Morton is a writer based in Seattle, where he obtained a PhD in cinema studies from the University of Washington. His work, which focuses on comics and animation, can be found in Literary Hub, Full Stop, and The Millions. His email is [email protected].


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