After a move to New York, Reggie Watts found inspiration and an audience for his off-kilter comedy-music hybrid

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Reggie Watts performs tonight at Webster Hall (Wendy Lunch Redfern)
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Reggie Watts could just as easily have stayed in Seattle forever.

He’d lived there since 1990, when he moved from Montana for art school at 18. Watts’s king-sized Afro and nonchalant demeanor made him one of the city’s most recognizable and best-liked musicians, and his band, Maktub, was one of its most popular. Sometimes he played solo, interspersing his songs with weird, deadpan jokes.

But Watts was growing restless, both with Seattle and with music; he wanted to follow the jokes. And so he did, moving to Brooklyn in 2004 to pursue a stand-up career. What could it hurt to try?

If you follow comedy even a little, you have some idea how that turned out. Watts’s bizarre improvisatory stage show—you couldn’t really call it a “stand-up routine”—led to an opening slot on Conan O’Brien’s “Legally Prohibited from Being Funny on Television” tour in 2010, and Watts has become a regular guest on O’Brien’s TBS show. Last week, Comedy Central aired “Reggie Watts: A Live in Central Park,” his second special for the network. (The first, in 2010, has the charming title Why S#!+ So Crazy?.) And next month, IFC premieres “Comedy Bang! Bang!,” a bent talk show hosted by Scott Aukerman, featuring Watts as its one-man “bandleader.”

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Watts, the son of a Frenchwoman and U.S. Air Force man, spent a few years growing up on European bases before his family settled in Montana. He left Seattle, he said over the phone last week, to make a hard mark between his music-first career and the comedy he now calls home.

“I spent a long time there, and [Seattle has] changed quite a bit,” said Watts, calling from the road that leads, tonight, to his headlining performance at Webster Hall.

“I think that the arts [in Seattle] became kind of pushed by the wayside a little bit. They want to essentially use the Vancouver model, centralizing the population, bringing back the city center, and building all these glass towers. I still have a few friends that still work out of there as artists, but it just doesn’t have that raw kind of feel anymore when I go there. I would probably move to Portland before I move [back] to Seattle.”

New York since 2004 has had a more wide-open feel.

“New York changed a lot, too, but it kind of dips around. It changes so quickly that you can find a place that you can hold on to—or if it disappears, you can always find a new place. I felt like you can sustain things here a little bit more easily. I had heard about Invite Them Up, [with] Eugene Mirman and Bobby Tisdale, in the East Village, and I saw Stella, and all of the ex-State members were doing theater at the same night. That's my brand of humor; that's what I crave. So I just knew that was the only place to really do it. That’s the only time you’re going to get the real experience, and also the potential of actually going somewhere with it if the right people see you.”

Comedy albums were formative for Watts.

“Eddie Murphy’s Raw, and Bill Cosby, or just watching specials on HBO like George Carlin, that was all a part of my upbringing. So yeah, it was important. Or even like David Cross’s Shut Up You Fucking Baby and a couple of the other albums on Sub Pop.”

The fact that Cross’s album—as well as titles by Eugene Mirman, Patton Oswalt, and Flight of the Conchords—was on Sub Pop proved crucial. The association made sense—those comedians all had an indie-rock sensibility—but it also worked as a bridge to comedy from the music side. Watts wasn’t the only musician to realize, These guys are doing what I’m doing, except they’re being funny.

“That just seemed to make sense, because in Seattle, seeing “Eightball” comics or Dark Horse Comics making a statement the way they did, and just underground culture [generally], it kind of made sense: kind of punk-rock company on a semi-punk rock label.”

It’s not like Watts has stopped singing entirely, of course. His stand-up act features a handful of songs—some fan favorites (“Fuck Shit Stack” from Why S#1+ So Crazy?, “Having Sex” from the new one—you see a pattern, yes?), some improvised on the spot, music and all. And like fellow comic Aziz Ansari, Watts has close ties to the DFA Records family: He was part of the “choir” for LCD Soundsystem’s final show at Madison Square Garden, and sang on the 2008 single “Spaghetti Circus” by local house duo Still Going.

“I was jamming with some musicians—essentially, the DFA house band. We started a band called Tippy Toes and we would play improv gigs at the Lucky Cabin, which is no longer in Williamsburg. That led to the attention of Liv [Spencer, half of Still Going], who asked me to come over and improvise some vocals. It only took a couple hours. It was in a big loft space right above the hipster mall in North 5th Avenue and Bedford.”

That versatility will be on display on IFC’s cable-TV adaptation of Scott Aukerman’s podcast, “Comedy Bang! Bang!” which premieres on June 8.

“The music for all the play-ins and play-outs [is] improvised in real-time,” said Watts. “The production crew really picked up on the sensibilities of how the podcast is run, which is generally Scott and a bunch of guests in a room around microphones, just free-forming all sorts of chaotic things. So the crew got used to being loose and doing things on the fly. I’m interested in seeing the reaction. It’s a talk show but it’s definitely very psychedelic and assertive and goes all over the place, kind of a mixture between ‘Pee-Wee’s Playhouse’ and ‘Mr. Show’ and ‘Between Two Ferns.’”

It’s also one of the first times—maybe the first time—a TV show has been inspired by a podcast.

“Unless you want to follow the trajectory of shows like ‘Amos ’n’ Andy,’” Watts offered. “Yeah, it started with radio. But podcast essentially is the new radio—like, on-demand radio. I think there’s differently a precedent. More traditional comedians might not embrace [the Web] as much, because they want to keep the jokes to themselves and do [them] live when they’re doing their proper shows. But a lot of my friends embrace the Internet. You [can] strike up a cyber-personal relationship with your fans. Someone’s like, ‘Great show last night,’ and I can immediately go, ‘Thanks a lot.’ It wouldn’t happen any other way. It makes sense that these larger-scale production ideas are coming from it.”

Watts’ biggest boost, of course, came from a more traditional kind of talk-show host. The Conan O’Brien tour wasn’t Watts’s first time playing in front of huge crowds—that would be when Maktub opened for the Dave Matthews Band at the Tacoma Dome—and he was more nervous appearing on the TBS “Conan” than winning over that comic’s sold-out crowds. Was Watts surprised with the somber tenor of the documentary film of that tour, Conan O’Brien Can’t Stop?

“It's hard with a film like that,” he said. “Conan admits this, and other people have admitted it in interviews: Sometimes it's hard because you're in a down state, but at the same time it's kind of like a privileged down state, but a person feels what they feel no matter what their situation is. So they're trying to capture that. But in hindsight, you've got a show that's doing really well”—here, Watts laughs—“people love him and he seems happy, so what's the deal with this show? You have to look at it like it's a record of how it was at that time. In that way, they succeeded.”

Not that the documentary jibes with Watts’s own memories of the tour.

“I think that it would have been interesting if they’d done another documentary, kind of a flip side documentary of some good times that happened as well,” said Watts. Then he laughed again. His good times, it seems, are just starting.