A curated guide to celebrity artists

George W. Bush, self portrait taking a shower

Recent revelations that George W. Bush had started painting portraits of himself naked in the shower as a pastime—and the rush by critics and pundits to compare his efforts to everything from outsider art to the work of Pierre Bonnard—got us here at Time Out New York to thinking about other well-known figures who like to make art. Granted, judged on merit alone, most works by celebrity artists would recieve scant attention. But the voyeuristic impulse to check out the artistic dabblings of the famous and infamous is a totally understandable urge. With that in mind, TONY presents this informal survey of art by some of the boldfaced names who’ve tried to follow in the footsteps of Leonardo or Picasso, with admittedly mixed results.

Early self-portrait by Adolf Hitler, done between 1908 and 1912

Art by celebrities could be classified as a subset of outsider art, since most of the practitioners are self-taught. But while technically outsider artists, they enjoy the ultimate insider status—none more so than the political leaders who, like Bush, have taken up the brush. Among this group, the most famous for being an artist is Adolf Hitler, whose career track to mass murder started arguably as the result of his derailed artistic aspirations—which were thwarted, of course, by a decided lack of talent. Case in point is this early self-portrait, depicting the future führer as literally unformed, a blank slate with a featureless face, seated somewhere outdoors on a log spanning a stream or culvert.

A self portrait by Sir Winston Churchill painted around 1920

Winston Churchill, one of Hitler’s great adversaries during World War II, was an avid amateur painter, devoting himself to the craft over the course of his life. This dark, brooding self-portrait dates from the 1920s, a period that marked the beginning of a low ebb in his political fortunes.

Dwight D. Eisenhower, portrait of Mamie Eisenhower

Both as Supreme Allied Commander in Europe during World War II and later in the White House, Dwight D. Eisenhower painted for relaxation; in fact, he and his ally Churchill often spoke of their mutual interest in art. In this portrait, he captures his wife, Mamie, as a benign if fuzzy presence, with a slightly bemused expression on her face.

Muhammad Ali, Mosque II, 1979

The world of sports has produced its share of celebrity artists, including boxing legend Muhammad Ali. He created this scene of a mosque in 1979, the same year he announced his retirement from the sweet science (though he would fight again in 1980 and 1981 before finally throwing in the towel). Although the rendering is naive, the image is a heartfelt testament to Ali’s Muslim faith, which he cited in his refusal to serve in the military during the Vietnam War.

Julianne Moore taken on the set of The Big Lebowski

The most fertile breeding ground for celebrity artists is indubitably Hollywood, if only because film stars can feel anxious sometimes about the cultural importance of their day jobs. Jeff Bridges, though, has made lemonade out of this particular anxiety-producing lemon. For years, he’s been bringing a panoramic Widelux camera onset to capture moments between takes. Fans of The Big Lebowski will recognize the Viking-costumed Julianne Moore from the fantasy sequence after the Dude has been knocked unconscious by a spiked drink courtesy of Jackie Treehorn.

Johnny Depp, Self - hanging upside down

Johnny Depp is either channeling Houdini or German upside-down figurative painter Georg Baselitz in this self-portrait.

Sylvester Stallone, Toxic Superman

While not technically a self-portrait, Sylvester Stallone’s superhero suggests an oddly aggrandized view of himself.

Are you surprised that painting is part of the creative portfolio of noted Renaissance man James Franco? We didn’t think so. But if you’re wondering whether the former Freaks and Geeks star takes himself too seriously or not seriously at all, this graffiti-inspired diptych offers evidence of both.

John Waters, Study Art Sign (For Breeding or Bounty), 2007

Some film-industry folks make plausible contemporary art, and even exhibit in the art world. One of them is bad-taste auteur John Waters, who lately seems to be concentrating more on his artwork than on his filmmaking.

David Lynch, Boy Lights Fire, 2011

David Lynch attended the prestigious Pennsylvania Academy of Fine Arts in Philadelphia, and has regularly mounted exhibitions of his macabre work. His last show was in 2012 at the Jack Tilton Gallery and included this piece.

Dennis Hopper, Fragmented Woman, 1965/2000

Dennis Hopper, the late star of Lynch’s classic Blue Velvet, was no slouch at making art. He was a serious collector, and his own output spanned numerous mediums, including painting, photography, sculpture and video. He was the subject of a 2010 retrospective at Amsterdam’s renowned Stedelijk Museum, which counted this sliced-up photorealist canvas among its offerings.

William Burroughs and Brion Gysin, Third Mind collage, 1965

Though it might appear a bit counterintuitive that celebrity artists would emerge from the ranks of famous writers, the literary demimonde has produced some notable examples. William Burroughs’s forays into collage, for instance, were of a piece with his approach to books like The Naked Lunch, which was written, in part, by randomly cutting and pasting together sections of text. Burroughs was aided and mentored by Beat Generation artist Brion Gysin, who co-created this ripped-from-the-headlines work on paper. Burroughs would later collaborate with such artists as Robert Rauschenberg and Jean-Michel Basquiat, and also expand into painting near the end of his life.

Kurt Vonnegut, Tralfamadorian #1, 1996

Kurt Vonnegut’s drawings and silkscreen prints owed something to the work of Paul Klee, and their sense of dark whimsy was very much in keeping with his writerly sensibility.

Victor Hugo, Ecce, 1854

Victor Hugo’s artistic accomplishments equaled his literary ones. This 1854 ink study, for example, rivals Goya in its unblinking depiction of man’s inhumanity toward man.

Slyvia Plath, Two women reading, left, Nine female figures

Sylvia Plath took art classes while attending Smith College, and she continued drawing and painting throughout her short life. The bright colors in these two paintings, however, seem at odds with her famously tragic end 50 years ago.

Frank Sinatra, untitled abstract painting from 1990

The music business has also birthed its share of celebrity artists. Golden-throated Rat Pack supremo Frank Sinatra, for one, started out by painting clowns and pets, but eventually evolved toward a style of geometric abstraction inspired by Mark Rothko and Barnett Newman.

Paul Stanley, Self Portrait

This self-portrait shows Kiss vocalist and rhythm guitarist Paul Stanley without his signature “star-man” makeup.

Don Van Vliet, Beezoo, Beezoo, 1985

Dada bluesman Captain Beefheart, a.k.a. Don Van Vliet, was a cutting-edge painter as well as a musician.

Marilyn Manson, Hand of glory, 2002

Shock-rocker Marilyn Manson does watercolors when he’s not busy fainting onstage. This one shows a naked woman holding a doll with one arm, while the other seems to be missing its hand.

Charles Manson, Waffen

While Marilyn Manson play-acts at being a cold-blooded killer, there’s another part-time artist named Manson who happens to be the real deal. Plus he has plenty of time to pursue his hobby, since he’s locked up for life. Jail time, in fact, may at least partially account for the prevalence of amateur artists among deranged murderers as a class.

John Wayne Gacy, Pogo the Clown

Besides other dubious achievements, John Wayne Gacy is the person most likely responsible for permanently linking the serial-killer profession to another—clowning. He performed under the moniker Pogo at hospitals and community events in his native Chicago, and the image of him in costume became a chilling leitmotif in his artwork.

Rural scene by Angelo Buono, aka the Hillside Strangler

Angelo Buono, a.k.a. the Hillside Strangler, also indulged in visual expression. This road, for example, is the one that should definitely not be taken.