This essay is excerpted from Andy Warhol: Love, Sex, and Desire. Drawings 1950–1962 published by TASCHEN.

Andy Warhol. Love, Sex, and Desire. Drawings 1950–1962 by Michael Dayton Hermann, Drew Zeiba, Blake Gopnik (published by TASCHEN)

One day, somewhere maybe around the summer of 1952, a rising commercial illustrator named Andy Warhol began to angle for a show of his “real” art in a new avant-garde space in New York. That was the Tanager Gallery, an artists’ co-op that counted several of Warhol’s art-school classmates as members. One of them was Joe Groell, who had also been a New York roommate of Warhol’s. He remembered Warhol approaching him with pictures of boys kissing that Groell found frankly embarrassing. Warhol’s boy-on-boy images “weren’t anything we wanted the gallery to be associated with,” Groell recalled, and he told Warhol the same.

Warhol tried again a few months later. This time he chose to make a cold call, wandering into the Tanager one winter’s day and presenting his portfolio to George Ortman, the member who was sitting the gallery. Ortman recalled being shown a picture of “two male full figures embracing.” He told Warhol there was no chance that such stuff could win a show at the Tanager, adding that the gallery was entirely devoted to abstraction — a lie, actually, but a white one that must have been meant to soften the sting of rejection.

Andy Warhol, “Male Couple” (ca. 1955) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

Sting or no sting, Warhol tried for the Tanager yet a third time, more than half a decade later. In December of 1959, Philip Pearlstein, another former roommate of Warhol’s who had been a much closer college friend, scored a hit with a Tanager show. The day after that show got praised in the New York Times, Warhol spent $300 on one of its pictures and was soon asking Pearlstein to get the Tanager to give him a chance at an exhibition. Yet again, Warhol was offering up gay imagery: pictures of boys “with their tongues in each others’ mouth,” according to Pearlstein.

But despite what Pearlstein described as his own best efforts, the gallery’s “macho oriented” members just could not see their way to showing such work. With the manly abstractionist Willem de Kooning established as the art scene’s “big dog” — in a studio next door to the Tanager, in fact — there was no way they would take a chance on a figurative artist who flaunted his effeminacy.

Andy Warhol (ca. 1957) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc. and Andy Warhol)

Three attempts at showing his “serious” art in a “serious” gallery; three portfolios of gay-themed pictures; three rejections. Warhol’s Tanager flailings have often been billed as the product of a certain cluelessness on his part, and on a gay identity that he just did not have the capacity — or the savvy — to repress, even when art-world success depended on it. But the explanation for Warhol’s triple attempt may be less psychological or biographical than properly artistic. He had good reason to believe that the daring gay imagery he was proposing was where art ought to have been heading at that particular juncture, and that if he only kept pushing his idea long enough, the art world would sign on. He was right, but also 50 years too early.

Warhol came honestly by his belief in the potential of queer subjects. Despite the dominance of abstraction out in the wider art world, the Pittsburgh of his youth had presented him with an artistic cutting edge that was all about figuration and the substantial content it could carry. The local art museum held prestigious annual surveys that favored socially conscious work. The political imagery of Ben Shahn was given especially big play there, and in the 1950s Shahn’s art was widely seen as the model for Warhol’s. Outlines, Pittsburgh’s superb if short-lived contemporary gallery, showed such content-heavy, progressive material as Soviet film and Käthe Kollwitz’s prints of “saddened women wrecked by war,” all meant to advance the founder’s belief that “modern arts, like modern sciences, bear directly on our lives and thinking.”

Andy Warhol, “Unknown Male with Stamps” (ca. 1958) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

The Carnegie Institute of Technology, where Warhol got his art degree, was equally dedicated to the social value and content of its students’ work. Warhol recalled being especially inspired by the art history course taught by a painter named Balcomb Greene, using a textbook that stressed the social functions and meanings of art and that described art history as “cultural and social geography.” Greene had first made his mark in the 1930s with a quite different approach to art, helping to found the American Abstract Artists group and to promote its uncompromising rejection of figuration. By the spring of 1947, however, just as Warhol’s sophomore year was winding down, Greene was turning his back on that past in a series of paintings based on photos of nude women that, as the New York Times wrote, stood as “his answer to the trend back toward the realm of natural appearances.” At almost the same moment that Abstract Expressionism was set to take over New York, and the world, Greene and others were sensing a countervailing tendency that was pushing vanguard art back toward contact with reality. This is the vanguard that Warhol was trying to push still further ahead with the pictures of boys he offered the Tanager.

Already at Tech, Warhol would have got hints that gay culture might be involved in that push. Although Greene himself was straight, his course notes show that Warhol would have heard him lecture on “the homosexual as an artist, and in the art world.” Warhol’s friend and classmate George Klauber was fully out; Warhol recalled that it was Klauber who first introduced him to the gay scene in New York, once the two met up there after graduation. On top of being gay, Klauber was also the most culturally advanced of Warhol’s classmates, fully informed about Picasso, Mondrian, and Proust in a way that his classmates — and professors — might not have been.

Warhol very likely viewed Klauber’s sexuality and sophistication as connected. In The Homosexual in America, a gay confessional published less than two years after Warhol finished at Tech, the author wrote about his community’s sense that “Our gay world is actually a superior one … that homosexuals are usually of superior artistic and intellectual abilities. Everywhere we look, we seize upon outstanding examples of brilliant people, either in our own circles or in the public domain, who are gay, or are supposed to be gay.” In Pittsburgh, Warhol would have found evidence to support such a view.

Andy Warhol, “Untitled (Male Portrait)” (c. 1956) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

Among several gay instructors at Tech, Perry Davis had been both the most openly queer and the most obviously and deeply invested in the latest moves and news of the wider art world. Most weekends, he invited his students to gatherings in his home, where they found support for their most avant-garde, even Dada ideas. At one such get-together, Warhol showed up with his hair dyed emerald, a move all his peers would have read as an obvious nod to a new movie called The Boy With Green Hair, whose title character suffers persecution, even beatings, because of his difference from his peers. In the movie, that queered character woke up one day to find himself altered, and he clearly wished that he were still “normal.” At Tech, Warhol was happy to take on his own alteration: not waking to green hair, that is, but choosing to green it himself; not trying to blend in, but wearing nail polish and a pink suit that would make sure he didn’t. One of his senior-year paintings was a full-frontal self-portrait that depicted him as a grade-school child, entirely naked except for a pair of girls’ Mary Janes and with his pinky stuck far up his nose, in obvious contempt for all the niceties. This was art, queerness, and rebellion all wrapped up in one carefully crafted package.

Warhol’s years at Tech had taught him that, in any modern art worthy of the name, mainstream rejection and avant-garde excellence were supposed to go together. As Balcomb Greene once said, “I advocate arrogance, not arrogance in painting, but complete arrogance,” and he welcomed any social consequences that might follow. (He and his sculptor wife, who dared to call herself Peter, were once arrested for punching a cop during a raid on a speakeasy.) Gays in Pittsburgh knew as much about mainstream rejection, and its sometimes life-or-death consequences, as anyone else, anywhere else. While Warhol was in college, two local judges declared homosexuality to be “society’s greatest menace,” triggering the creation of a vicious new police squad whose only job was to root that menace out — via shootings, beatings, or extortion, if need be.

So as Warhol first made his way to New York, just then emerging as a rival to Paris as the art world’s capital, his head would have been filled with the idea that significant art ought to involve significant, even defiant content, and that the most defiant content of all might involve queerness.

Andy Warhol, “Male Nude Lower Torso” (1956–57) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

Not too long after his arrival, Warhol had found some New York confirmation for a connection between queerness and the avant-garde. In the summer of 1952, he actually won a solo show — his first — thanks to a portfolio of images probably not too far from the ones he first took to the Tanager around the same time, and which he assembled into an exhibition called Fifteen Drawings Based on the Writings of Truman Capote. The gallery hosting his show, called the Hugo, was known for its dedication to the most radical of European modernism, which still had shock value in New York: Bloodflames, a notorious group show at the Hugo, had been reviewed as “the extreme of the extreme” and earned the Times headline “Modernism Rampant.” That “rampant” might as easily have been applied to the gallery’s owner, a wildly flamboyant former ballet dancer named Alexander Iolas, who claimed to have offered Warhol that first exhibition right after spotting him on the street as a kindred spirit. Bringing together radical modernism, blue-velvet walls, and an extravagantly fay owner, the Hugo Gallery that welcomed Warhol’s Capote drawings could only have confirmed the connection he had made at Tech between queerness and avant-garde promise. It’s no wonder that Warhol’s failure to connect at the Tanager, a lesser venue than the Hugo by most standards, might not have completely discouraged him.

In 1950s art circles, it was well established that the inconvenient, even time-wasting labors of commercial art had the upside of letting serious artists get on with their “independent work, free of economic care,” as the catalogue to one notable exhibition put it. In Warhol’s case, even as he made his name and fortune in safely salable illustration, his personal projects were indeed independent, in the extreme, and distinctly uncommercial. If boys kissing boys got him nowhere in public — even his tamer Hugo pictures had barely been reviewed — in private his art went much further than mere osculation. This current volume’s gay imagery, ranging from merely suggestive to frankly pornographic, represents just a small sampling from the many hundreds of queer pictures that survive from Warhol’s 1950s art, and even those represent only a fraction of what he must have produced in the same genre, since we know of several later moments when Warhol destroyed piles of his early work.

Andy Warhol, “Standing Male Nude Torso” (1950s) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

Endless stories have come down to us about the overheated drawing sessions that provided Warhol’s subject matter. “Andy had this great passion for drawing people’s cocks and he had pads and pads and pads of drawings of people’s lower regions,” said a queer friend and assistant of Warhol’s. “They’re drawings of the penis, the balls and everything, and there’d be a little heart on them or tied with a little ribbon. … Every time he got to know somebody, even as a friend sometimes, he’d say, ‘Let me draw your cock.’ … They’d drop their pants, and Andy would make a drawing. That was it. And then he’d say, ‘Thank you.’”

Warhol had begged one new acquaintance to reveal his “big meat” so he could draw it. “And before I knew it — we were all very young and silly — I was sitting with my pants down, with a daffodil wound around my dick. That was my first meeting with Andy.” These accounts, and several others like them that are much less demure, have always seemed to bill Warhol’s dick drawings as the product of an amusing, hands-off voyeurism — as something closer to a sexual and social practice, that is, than to a truly artistic one. There may be some germ of truth in that, but it’s counterbalanced by the real avant-gardist dividends that the drawings paid to art lovers with the sense to understand them — a group that, in the 1950s, may have included Warhol himself as just about its sole member.

Andy Warhol, “Unknown Male” (1950s) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

The 1950s were, after all, the heyday of formalist criticism — of talk that was all and only about such things as color, form, and composition. Novelty in style was the mark of important art. And as critics complained at the time, Warhol’s drawings didn’t have much new to say on that front: Their style had strong and obvious roots in earlier innovations by the likes of Ben Shahn, Henri Matisse, and Jean Cocteau. What the critics were not ready to see — and mostly couldn’t handle even once Pop came along — was that Warhol’s innovation lay in using accepted styles, sometimes almost no style at all, to give a transparent window onto the novel content he wanted to show. Without the distractions of style, that is, Warhol could play a game of show-and-tell that was much more about showing than about how it chose to tell. Just pointing at what matters to you in the world — simple ostension, to borrow a term from philosophy — became Warhol’s radically new aesthetic gambit. It reached its maturity with the uninflected, style-free pointing of his Campbell’s soups and Brillo boxes, but it got its start in the drawings of his gay friends.

Warhol did eventually get to show a sampling, at least, of his queer drawings, in an exhibition called Studies for a Boy Book. The exhibition seems to have been mostly chaste portraits of Warhol’s crushes, with maybe a few nudes with pubic hair and nipples romantically covered in hearts. This was the first of several shows that Warhol received at the Bodley Gallery, owned by a man who had assisted Iolas in mounting the Capote show at the Hugo. Warhol’s Boy Book exhibition ran for just two weeks, in 1956, beginning on Valentine’s Day, which gives some indication of the gay clientele that the gallery appealed to. It showed work by Stephen Tennant, the queer English dandy, and by an artist who did “tender and observant, slightly obsessive paintings of adolescent body builders,” according to a rare Bodley review in the Times.

Andy Warhol, “Seated Male Nude” (1950s) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

The Bodley was just up the street from Serendipity café, a favorite locale for Warhol and the scene’s other “window-decorator types” (that’s what Capote himself called them), and not far from the so-called Bird Circuit of gay bars in the same neighborhood. That did not bode well for the exhibition’s reception out in the wider world. One newspaper gave it a review that counted all of 33 words, four of which proclaimed it to be “in sometimes doubtful taste.” The prestigious Art News magazine gave it one more word than that, while omitting almost all description of what the drawings actually depicted; while a review in the Times, any New York artist’s holy grail, went on for a whole 36 words, but with no more specifics than a nod to the drawings as being “sly” and full of “private meaning” in a Jean Cocteau mode — code, for those few who could read it, for the drawings’ gay slant.

So the lesson that Warhol must have taken from this first “success” at the Bodley, coupled with his multiple rejections at the Tanager, is that an audience for this, his most truly radical work, could be found only within a gay ghetto. And that was simply an insufficient audience for a ferociously ambitious artist like Warhol, especially since the modernist transgression of his gay imagery seemed to be taken, in homosexual circles, as evidence of nothing more than someone having some good, queer fun.

That may explain why, as Warhol ramped up his hunt for fine-art success in the early 1960s, the Pop pictures he devised — still bravely representational and content filled — had only the subtlest traces of gay content. (The Campbell’s soup can, with its fin-de-siècle label, was read by some gays as a camp icon; Warhol included a dishy musleman in a painting not too long after the Bodley showed its bodybuilder paintings.)

Andy Warhol, “Untitled (Feet with Campbell’s Soup Can)” (c. 1960) (copyright © the Andy Warhol Foundation for the Visual Arts, Inc.)

Roy Lichtenstein, Warhol’s colleague-in-Pop, remembered how their new movement was born of a desire to shock, in a buzzing art world where that had become all but impossible: “It was hard to get a painting that was despicable enough so that no one would hang it — everybody was hanging everything. … The one thing everyone hated was commercial art.” So that, of course, is what Warhol and his peers built their revolution around. Yet the one thing “everyone” hated even more than commercialism — hated so much that its shock value was too great to be safely incorporated into the latest vanguard of American art — was gay culture. Only the outrageous, unlikely success of Pop art, and the gradual advent of a full-blown ’60s counterculture, gave Warhol permission to venture into the public homoerotics of films such as Sleep and Blow Job.

“Everybody knows that I’m a queen,” Warhol said. But it took him almost until his death to say it.

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Blake Gopnik

Blake Gopnik was the chief arts critic of the Washington Post between 2000 and 2010 and is a regular contributor to the New York Times. His definitive biography of the artist Warhol...