People will react to a man in a pink dress carrying a boombox down 14th Street NW in three ways. Some will pretend it’s something they’re used to seeing. Others will laugh. But most will just smile nervously, as if they suspect they’re being surveilled.

“There’s something liberating about making art that at the end of the day a lot of people are going to think is bad,” says Jeffry Cudlin, the man in the dress. Cudlin’s 14th Street jaunt was part of his tour last Friday of Washington art galleries, each of which he tried to turn into a dance party.

Cudlin, who writes art criticism for Washington City Paper, intended to make a video of the gallery tour as part of his upcoming show, “By Request,” which opens later this month at Flashpoint. For the exhibition, Cudlin asked seven local arts notables to complete surveys about art, art spaces, and themselves. Then, seven local artists created works that draw from survey data. In an intentionally egomaniacal twist, each of them must also depict Cudlin. It’s all supposed to say something interesting about celebrity—a challenge in a post-Warholian art world, but by no means the least of Cudlin’s worries.

For one thing, pink leopard-patterned dresses don’t come in his size. As Cudlin gyrated to a Grace Jones tape inside Conner Contemporary Art on Florida Avenue NE, the dress frequently rode up to reveal his ass. “Extra-large doesn’t mean 6-foot-4 man,” Cudlin laments.

Cudlin in drag is meant to be an impersonation of Philippa P.B. Hughes, the local art-events planner behind the Pink Line Project. Hughes rides a pink scooter, so Cudlin had to ride one, too—something he’d never done until Friday. His pink helmet barely fit over his blond wig. Riding just a few feet to 14th Street’s Curator’s Office, Cudlin nearly hit a tree.

Over the past few months, Cudlin has lost 30 pounds, had his legs waxed, and learned to dance in heels in the name of bad art. Watching him nearly grind on Curator’s Office director Andrea Pollan and a pair of surprised interns in Hemphill Fine Arts, I had to admit: The freckly giant is pretty sexy.
“He moves that cassette like a weapon, doesn’t he?” said one onlooker.

Hughes insists that Cudlin’s dress wasn’t quite accurate—it’s too short. “I’m just summoning the fantasy of the sexual-libertine Philippa,” Cudlin says, after a pause adding, “which doesn’t really exist.”

The most common complaint passersby had was that Cudlin, despite his wig, fake breasts, and clear high heels, just didn’t look enough like a woman. Cudlin’s red goatee and thick arm hair were popular targets.

“He should have shaved his arms!” a man standing outside a liquor store yelled at Cudlin, who says he wasn’t going for verisimilitude. Rather, he wanted to present a superficial image of Hughes.

“You already know I’m a guy in drag,” Cudlin says. “Why does having a goatee wreck that?”

Photos by Darrow Montgomery.