PERHAPS THE LESS one knows about Reggie Watts, the better. Certainly he doesn't mind.

"I just think it's fun," says Watts of taking the stage before an audience that's unfamiliar with his work. "Especially in the traditional comedy club where a bunch of people get together," and here Watts adopts a nerdy vocal affectation, higher and more tightly strung than his deep, relaxing baritone. "Let's go see some comedy!" he croaks.

The table is set. The misdirection may begin. He's going to take the stage impersonating a traditional comedian.

"I'll do stand-up-like stuff," Watts says, back in his own voice. I can hear his grin. "I love that. Then I flip it."

For a lot of touring headliners, appearing before an unfamiliar and perhaps unsympathetic audience can be nightmarish. Especially for more eclectic performers.

Yet there are few stranger than Watts. At times it's hard to know what to call him. He's a stand-up, in that he takes the stage alone and makes people laugh. But measured against American comedic tropes of honesty, voice, and the sharing of self—not to mention the cliché of comedic sensibility having dark origins—Watts is an iconoclast. He didn't have a rough childhood. He doesn't find it hard to communicate offstage. His work doesn't come from pain.

More importantly, he doesn't write jokes. And for every impersonation, non sequitur, or leap of consciousness, Watts is just as likely to start singing.

He'll start with a bass line, humming it into his looping pedal, or maybe a beatbox. Then some "oohs" and "ahhs," perhaps in harmony. It's funk. And continuing in real time, with astonishing breadth and vocal dexterity, Watts layers piece after piece. When the composition is ready for lyrics, Watts' concoction becomes beholden to whatever's piquing his interest that second. It might be lunch. Or, just as easily, leprechauns and magic beans. No matter the subject, nothing is pre-written, musically or otherwise. Like everything Watts does, the songs are improvised.

Ever since he began doing stand-up in high school, Watts has performed off the cuff. His career trajectory—and perhaps his life in general—appears to have been governed by the same principle: Stay in the moment. So far it's worked exceedingly well.

Last spring Watts was selected to open for Conan O'Brien's Legally Prohibited from Being on Television tour. It was a press bonanza. Not long after, Comedy Central released an album and TV special. But to Watts it didn't feel like a wild or lucky break. "Because I'm improvising," he says, "it can lead me anywhere."

From more alternative comedy and performance art beginnings, the ethos has, perhaps paradoxically, led Watts closer to the mainstream, but not yet to the point where he'll be playing to built-in audiences in Middle America. There Watts encounters crowds who've been herded in like cattle. The kind he likes to flip.

And although the upcoming tour is his first as a headliner, Watts says he's evolved to become comfortable coming up with an hour-plus of fresh material for each set—even sometimes twice a night. Nonetheless, while improvising there's no telling where things will end up.

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"I think it's just the ability to reflect something or project something to people that shows the ridiculousness of situations," Watts says of his comedy. "Especially small situations.

"But it's really that ability to get people on board with something ridiculous," Watts continues. "To show how the things they think of as serious or mundane are just stupid and over-inflated. It's nice to be able to work with very little and make a huge thing with something so small."

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In person at the Clinton St. Theater 10/29 & 10/30