Of all the challenges Conan O’Brien faces on his nationwide “Legally Prohibited From Being Funny on Television” tour (translating his talk-show aesthetic into a live comedy performance; avoiding coming off as a sore loser), the biggest challenge might be self-inflicted: having to step onstage every night in the wake of his opening act, Reggie Watts. Watts, a star of New York’s alt-comedy scene, is the kind of comedian who tends to close shows. His sets are loud, disorienting bouts of improvised anti-comedy. He is, in many ways, the opposite of O’Brien, as both a performer and a being. O’Brien is gangly and pale; Watts is chubby and dark. O’Brien has an ironic post–Tonight Show beard and that signature little flip of orange hair; Watts has a huge asymmetrical Afro that blends into a beard as thick and dark as good-quality garden loam. O’Brien approaches comedy, famously, as a writer, spending hours preparing each moment onstage. Watts improvises his act so thoroughly that, if a hard-core fan were ever to request a favorite old bit, Watts would probably have no idea what he was talking about. Over the past seventeen years, Conan has established himself as one of America’s most stable comic voices. Watts builds his comedy out of radical instability: He switches so fluidly among different accents and personae (soprano, baritone, Californian, Cockney) that it’s hard to tell what the real person even sounds like. Conan, in other words, is a recognizable type of comedian: a subspecies of the genus Letterman. Watts is like a character Conan might have invented—half-man, half-astral-funk Muppet.
more from Sam Anderson at New York Magazine here.