Comedy and music usually go together like kumquats and mayonnaise. Very few artists can meld the two disciplines into a harmonious act and sustain a career. Former Seattleite Reggie Watts, though, is one of the most luminous luminaries of what we'll call—just this once—chucklesonics.

You may remember Watts's massive Afro, full beard, and expressive vocals at the front of Seattle quartet Maktub, which flourished from 1996 to 2007. They excelled at buttery, uplifting funk and R&B with occasional forays into rock. Maktub's music is straightforward, sincere, and accessible. Similarly, Watts's 2003 solo album, Simplified, drips with earnest, heartfelt sentiments framed in a conventionally sensitive R&B-loverman/soul-singer context. Nothing in these romance-and-dance-oriented recordings hints at the hilariously absurdist humor that's sprouted forth in copious quantities since Watts moved to New York City in 2004 to focus on comedy.

"[New York] was a good change of pace, because I felt like I kind of maxed out in Seattle," Watts says in a phone interview. "I wanted a new location that was more entrenched in the tradition of comedy. So New York was the way—still is. I wouldn't be where I'm at without it. There's no industry in Seattle for comedy, really. It's one of those weird catch-65s."

Watts's New York connection started when he began writing songs for the band Soulive; he'd do standup sets before the group would play. His initial break came when he performed at a comedy night thrown by Eugene Mirman and Bobby Tisdale. They dug him and Watts felt accepted. There was no turning back after that.

Watts's stunning act relies on spontaneity and wit, of course, but also his deep, wildly diverse well of musical knowledge, which enables him to inflate the conventions of several genres to ludicrous dimensions. (His favorites include the Smithereens, the Smiths, James Brown, Bauhaus, Soundgarden, and Ministry; he also got into drum 'n' bass, triphop, and acid jazz in the 1990s and was classically trained on piano and violin as a child in Montana.) Watts coaxes maximal laughs through the exaggerated stressing and extrapolating of musical and lyrical minutiae—plus the sort of inventive beatboxing that could give Jamie Lidell night sweats. And it's all stream of consciousness.

"I'm chicken-winging it," he says. "The only structure is I know I can do something on the keyboard, I can do something with my looping machines, and I can do something with the microphone. I know I can start on any one of those or not use one at all the whole time."

You can witness Watts's improvisational brilliance on several YouTube videos from his appearances at international comedy festivals and on Conan O'Brien's TV show, and on his Why Shit So Crazy? CD/DVD. The breakout cut from that sporadically riotous album, the vicious hiphop-cliché deconstruction "Fuck Shit Stack" (3.25 million views and counting on YouTube), was cowritten with New York playwright Tommy Smith; they also collaborated on the viral video "What About Blowjobs?" and the long-form multidisciplinary presentation DISINFORMATION.

"What makes [Watts] stand out is that he has the Line 6 sampler, and he's able to play it like Jimi Hendrix played a guitar," Smith says. "Is this comedy? I've always seen it as pulling a Guy Debord—Reggie is using the venue of comedy to do a situationist performance-art routine."

Smith's perspective is indicative of how Watts's art works on multiple levels. His routines range from utterly silly to slapstick to starkly serious and highbrow. Key to his appeal is his ability to shift personae on a dime and his on-point mimicry—and sending up—of numerous personality types. Of comedy's two main modes—escapism and enlightenment—Watts's seems more slanted toward the former.

"My favorite comedy is both," he contends. "But escapism can be a form of enlightenment. It's about attaining a better perspective on life. If you escape and turn around and look at where you escaped from, you have a better idea of where you came from. I think the enlightenment is in the laughter. I think all laughter is enlightenment."

Watts admits that the most defining trait of his act is absurdity, and he ranks as a master of that worthy condition. "You can't take life too seriously because the universe is far too silly of a place," he says.

Is the absurdity a Montana thing? "It's definitely not a Montana thing. I think it was just me loving silly shit. Monty Python's Flying Circus really opened my eyes. Seeing Monty Python and the Holy Grail opened my eyes to abstract absurdism. Silly for silly's sake—putting so much effort into a stupid idea. That's brilliant. That's where I fell in love with that whole idea."