The good looks of playboy have always extended beyond the pictorials. Art has been central to the spirit of the magazine ever since Hugh Hefner launched it in December 1953; Salvador Dalí, Alberto Vargas and Patrick Nagel are just a few of the game-changing artists whose work has adorned its pages. Soon after Hef published our first issue, another cultural juggernaut began to emerge in the United States: pop art. As both the magazine and the movement evolved, it was perhaps inevitable that their paths would cross. “America’s prince of pop”—as playboy christened Andy Warhol in 1967—had a nearly 30-year relationship with the magazine. Here, we revisit playboy’s history with Warhol and three other heavy-hitting artists associated with the pop movement: James Rosenquist, Tom Wesselmann and Keith Haring. Several of the pieces shown here, from Polaroids to prints, have never before been published.


ANDY WARHOL


Warhol’s first Playboy commission came in 1961: a painting that ran in Show Business Illustrated, a short-lived Hefner publication. By 1967, when his first playboy piece appeared—a double silk screen of a female torso—Warhol was a full-blown pop-art phenomenon. He also provided the artwork for a 1969 playboy profile of him. Created on a copy machine, the pieces were “perhaps the most extraordinary self-portraits that he ever made: a group of seven death-mask-like images,” writes curator Charles Stuckey in our January 1990 retrospective. Warhol’s only playboy pictorial appeared in 1974; Instant Warhol begins by introducing the “lensman who seldom goes ahunting without his trusty Polaroid.” Shown above with said camera, Warhol arranged the images into photo collages. The Polaroids of actresses Patti D’Arbanville and Dominique Darel are outtakes, unpublished until now.

Talk about triple-strength star power: In the January 1984 playboy, infamous author Truman Capote memorialized playwright Tennessee Williams, and Warhol, art royalty at that point, illustrated the remembrance. He submitted two silk-screen prints built on outtakes from the portrait session for Williams’s April 1973 Playboy Interview, including the purple-and-yellow version shown here. The black-and-white photo it’s based on appears in the magazine for the first time. For the main image, Art Director Tom Staebler selected the more dynamic red- and blue-hued piece, a color scheme echoed two years later in Warhol’s most famous work for playboy: his Rabbit Head, which graces the January 1986 cover. “I’ve got bunnies on the brain,” Warhol said at the time.


James Rosenquist



“I’m the one who gave steroids to pop art,” remarks James Rosenquist in his memoir. Indeed, his 16-by-seven-foot, two-canvas Playmate as Fine Art—named after the 1967 article it appears in—is on the small side for a Rosenquist; no wonder playboy described the erstwhile billboard painter as “one of the principal detonators of the pop explosion.” With its depiction of glistening strawberries and cream, a wire basket, breasts and a pickle, Playmate tells a beguiling tale; in 2009 The New York Times homed in on its “basketball-size areolas.” Rosenquist’s diptych was displayed at the magazine’s 25th anniversary party in the Chicago Cultural Center, where Hef, July 1977 Playmate Sondra Theodore and others celebrated.


Tom Wesselman



Wesselmann supersized a pair of luscious lips for playboy’s January 1967 feature The Playmate as Fine Art. “I chose to do a huge cutout mouth in order to isolate and make more intense the one body part that has a high degree of both sexual and expressive connotations—but then painted a mouth with low degrees of each quality, to keep it, like the Playmate, somewhat glossy yet inviting,” he said. The oil painting, Mouth #8, sold at auction in 2010 for $1.9 million. 


Keith Haring


Haring rose to prominence in the 1980s as a muralist with a gift for bridging low and high art. His colorful graffiti-style pieces often tackled social and political issues—AIDS, drugs, inequality. playboy published several of his illustrations in 1986—in fact, works by both Haring and Warhol appear in that year’s January issue. Haring could be said to have picked up the pop mantle from Warhol, whom he considered a friend and mentor. “You see,” Haring says in his authorized biography, “whatever I’ve done would not have been possible without Andy. Had Andy not broken the concept of what art is supposed to be, I just wouldn’t have been able to exist.” Haring’s playboy illustrations accompanied both fiction (a comic story by Robert Sheckley) and nonfiction (a profile of self-help marketing genius Tom Peters). The magazine commissioned but never ran Bunny #2, also known as Bunny on the Move; it appears in our May/June for the first time in playboy’s editorial pages. 

A pop-out from the pop artist: playboy gave readers a Christmas treat in December 1986—an exclusive Haring-designed ornament printed on pre-cut paper. The same year Haring opened his famous SoHo store, Pop Shop, to bring his art to the public.