Geoffrey Chadsey is a man in his mid-30s who gets weird looks from supermarket checkers for buying Tiger Beat magazine. He cruises Internet chat-rooms searching for pictures and images of young men in various stages of revelry and undress. No, he's not a congressman. He's an artist, and his interest in the puerile is not what you think.

Chadsey creates large drawings in watercolor pencil. He seeks images from art history, the Internet, family albums and the outer edges of popular culture. Through technique both naturalistic and surreal, he renders witty, disturbing portraits of American men who, in their pursuits of happiness, find something closer to misery.

"If you want to experience a break in reality and feel like an inappropriate adult, buy a teen magazine at a supermarket check-out," says Chadsey, whose work is on view at The Contemporary Museum in "Boys In The Band: Geoffrey Chadsey Drawings, 1998-2006," his first solo museum exhibition.

Chadsey, of course, is not an inappropriate adult. He understands that in a culture dominated by the glorification of celebrity, where youth is simultaneously revered and debased at every turn, an artist has a right, if not a responsibility, to ask viewers to consider the difference between ugly and beautiful, between appropriate and pathetic.

Much of the subject matter in a Chadsey drawing comes from the juxtaposition of faces and bodies from different sources. The Tiger Beat might give him a young face to superimpose onto the body of a drunk man he found in a photo on Google. The face and body may be placed in a room that resembles the artist's studio, and the whole picture may be drawn in colors that appear unnatural, like cartoons. Images from reality turn into something otherworldly. In a series of funny portraits of historical figures, the artist draws Einstein's face on a head groomed with cornrows. George Washington has Beyoncé's hair and holds a guitar that Chadsey borrowed from a friend. (Who knew that the father of our country bore such an uncanny resemblance to Melissa Etheridge?)

So what, exactly, is Chadsey up to? Why, for example, does he draw a picture of two men in a hot tub, and why did he give one of the men the face (but not the body) of Xzibit, the rapper? To begin to answer such a question, one really needs to see the show, but Chadsey's hip-hop images provide some clue as to what he's doing.

"Music is a huge engine of my work," Chadsey remarks to a gallery full of onlookers during a Contemporary Museum walkthrough on a recent Saturday morning. The Brooklyn-based artist, who was in town for the exhibition opening, explains his interest in sampling, the practice in hip-hop and contemporary dance music of taking beats and sounds from one song or composition and placing them in another to create a new work, a kind of musical collage. "When I first heard sampling, I thought it was the most revolutionary thing I'd ever heard."

If his drawings are informed by sampling and pastiche, they are also the products of a photographer's eye. A good photograph turns reality into something personal, specific and universal at once. Chadsey draws viewers into these visual mash-ups, and, to make sense of them, we have to consider issues of vantage point. Where has he placed himself as he views his subjects? How has he positioned the viewer? Should we laugh at the image of the old naked guy who reaches out to us from his bed? Should we view the artist and his creations with disgust?

By trolling popular culture and the Internet for images of young men, Chadsey evokes the malicious stereotype of the predatory gay male. Because he creates art out of this stereotype, the work has a confrontational, political impact.

By mixing images of marginalized gay men with Snoop Dogg, Xzibit and other hip-hop luminaries, the artist pits two stereotypes against one another. The popular conception of the gay lifestyle stands as antithetical to the popular conception of the gangsta lifestyle. In Chadsey's hip-hop drawings, two extremes of masculinity — its depletion and its overabundance — collide to disturbing, stunning effect.

Though black men and gay men have historically been vilified in different ways, they have both drawn the fire of those who demonize their sexuality.

Chadsey uses his brother, father and sisters' faces in many of his drawings to add questions of family to his sociological stew. Where does the author's sense of masculinity come from? Where does a gay man go when he wants to reject the stereotypes that have been presented to him? Where do human beings find examples of love and truth when the popular manifestations prove so elusive, so faulty?

To focus only on questions of culture or to define Chadsey only as a gay artist diminishes the sheer technical skill with which he draws. As striking as his foregrounds are, with their playfully demented central figures, his backgrounds command attention with their subtle, sophisticated beauty. Look at the rugs on the floor and the shadows cast by crests in the sheets on the bed.

The artist jokingly referred to one of his figures as an "effeminate, slightly hostile gay Frankenstein." Geoffrey Chadsey is less mad scientist than alchemist for the way he turns demons into art.

Timothy Dyke is a teacher at Punahou School.