Reggie Watts is at Helium tonight and tomorrow. He'll be joined by the marvelous Ron Funches and Ian Karmel. For a little primer on Watts, check out my piece in this week's print edition. For the story I spoke with Watts, who was in Montreal at the Just For Laughs Festival at the time. We talked his recent rise, his origins in comedy and more. Find it all after the jump.

TONIGHT: Reggie Watts @ Helium w/ Ron Funches & Ian Karmel

TONRY: HOW LONG HAVE YOU BEEN HEADLINING, DOING A FULL HOUR? IS THAT A NEWER DEVELOPMENT?

WATTS: This tour that I'm going to do in August is the first 'official' headlining tour.

YOU WORK PRIMARILY THROUGH IMPROV. HAVE YOU HAD TO CHANGE THAT AT ALL? HOW HAVE YOU GONE ABOUT BUILDING THAT HOUR?

I don't really build it. It's just, kind of, me getting better at filling up an hour of improvising. That's mainly what it is.

IT HASN'T FUNDAMENTALLY CHANGED HOW YOU APPROACH THINGS?

It's just all a cumulative experience. It's weird. It's just kind of a natural evolution, like growing from a teenager to a young adult. It's happening, but you kind of don't notice it. Now suddenly I'm doing an hour and I'm like, 'oh, I don't even remember when I was doing shorter sets.'

HAVE YOU EVER GOTTEN INTO TROUBLE IN AN HOUR?

Not so much lately. But I have in earlier days when I was just starting to try to do hours. I would definitely get fucked up a little bit, or I would just lose track of the energy or people would get annoyed.

DO YOU EVER CROSS PATHS WITH TRADITIONAL COMEDIANS WHO SCOFF AT WHAT YOU DO? I KNOW THEY HAVE DISDAIN FOR A LOT OF PROP COMICS AND MUSICAL ACTS...

I haven't had anyone come up to me in my face and say something. Most cats are cool. They're really cool because I'm lucky to be doing what I'm doing in that circle and what I do is very very different from most people in that circuit. So for them, there's nothing really threatening about it. I'm not stealing they're material. I'm not stealing ideas. They're not threatened by me in that way. It's great 'cause everyone can just chill and not worry about shit.

WHAT IS YOUR RELATIONSHIP WITH PORTLAND? I FEEL LIKE THERE WAS A TIME WHERE YOU WERE POPPING UP AROUND HERE SOMEWHAT OFTEN.

I really like Portland a lot and I was considering moving there for awhile. I spent a lot of time there and dreamed of moving there. I may move there one day.

ARE YOU STILL HOMELESS, JUST FLOATING WHEREVER THE WORK TAKES YOU?

Now I have a place in Williamsburg, an apartment with stuff in it. And I have keys to it. So I'm not really floating around. I have a home base. But I also have a girlfriend who lives in Belgium so I go back and forth between Belgium and New York.

WHEN CONAN'S TOUR CAME ALONG, WERE YOU WORKING OR PLUCKED FROM SOMETHING ELSE? WHAT WERE YOU UP TO BEFORE HE CAME KNOCKIN'?

It's more of that evolution. Because I'm improvising it can lead me anywhere, so it was surprising, but it was a nice step to get on.

WHAT DID SEEING CONAN PERFORM AND GETTING TO KNOW HIS TEACH YOU?

He's inside of these Big Show situations. In music I've played, on occasion, I've opened for some big bands. I've played stadiums. I've played in front of like twenty-to-thirty-thousand people, more as a musician. But comedy's a bit more personal. Also in comedy, playing to like two-thousand to five-thousand people is huge for comedy. The scale is different. So it's not going to be constant with that scale, doing what I do.

WAS THERE ANYTHING YOU COULD PICK OUT OF HOW HE DID IT THAT YOU LEARNED WATCHING HIM?

What I do is kind of what I do. The good thing about it is it's not really a lot you can change. You just line up and get ready to go.

WHEN YOU FIRST TRANSITIONED FROM MUSIC TO COMEDY DID YOU TRY OTHER FORMS? WERE YOU EVER DOING MORE TRADITIONAL, PRE-WRITTEN MATERIAL?

I started comedy in High School, so it was kind of pickup up where I left off. I was improvising and doing characters, mixing music and stuff. It was kind of stuff that I was already developing.

WELL SURELY THE LOOPING PEDAL DIDN'T EXIST WHEN YOU WERE IN HIGH SCHOOL?

There was no looping equipment at all back then.

BUT IT WAS ALL IMPROV, EVEN BACK THEN? YOU NEVER SAT DOWN AND WROTE?

Things become structured as I improvise over and over again. I could definitely create a show over time. But I never sat down and wrote it out. It was just kind of muscle memory, back in the day. Now I kind of leave it up to total improvisation, unless I'm not feeling connected, and then I can kind of go back on other bits I've done before.

ANY WRITING IN OTHER PARTS OF YOUR WORK? OR IS EVERYTHING YOU DO SIMPLY GOVERNED OR DRIVEN BY IMPROVISATION?

I just kind of go through the day and just kind of riff on it and it kind of filters down into that end product experience on stage. Sometimes occur to me live, on stage, and sometimes stuff that I've thought would be fun to do on stage I'll actually remember when I'm on stage, which is nice. It's really just kind of noticing stuff and just letting it float around and seeing what happens when I get up on stage.

I IMAGINE WHEN YOU GOT UP ON STAGE AND NO ONE KNEW WHO YOU WERE. YOUR CAPACITY TO SURPRISE THEM WAS REALLY ABUNDANT. I WONDER HOW IT'S CHANGED FOR YOU NOW, WITH PEOPLE COMING KNOWING WHAT—OR AT LEAST WHO—THEY'RE GOING TO GET?

It feels like I still have that surprise element to it because those people who know I'm improvising never really know what I'm going to do—because I don't. But I still run into plenty of audiences I've never seen, which is nice.

IT MUST HAPPEN AT THE OLD SCHOOL COMEDY CLUBS WHERE THEY JUST WRANGLE PEOPLE IN THE DOOR.

I love that. I just think it's fun. Especially in the traditional comedy club where a bunch of people get together like, 'let's go see some comedy!' And I come up and I love playing the stand up at first. I'll do stand up-like stuff, full out and I love that. That's my favorite. Then I'll totally flip it.

WHEN YOU TALK ABOUT TRADITIONAL STAND UP, A LOT OF COMICS WOULD SAY IT'S ABOUT SHARING PARTS OF YOURSELF OR BEING HONEST, AND I THINK YOUR ANGLE IS INTERESTING—SURELY IT'S THE OPPOSITE, BEING ABOUT CONFUSION OR MISDIRECTION OR SOMETHING COMPLETELY DIFFERENT. AND I WONDER IF YOU HAVE AN IDEA OR A MEANING OF WHAT YOU THINK COMEDY IS OR REPRESENTS?

Comedy is a subjective thing. I think it's just the ability to reflect something or project something to people that shows the ridiculousness of situations—especially small situations. Or it can be a large scale concept. But it's really that ability to get people on board with something ridiculous to show how the things that they thing of that are serious or mundane are just stupid and overinflated. It's nice to be able to work with very little and make a huge thing with something so small.

SO THE IDEAL WOULD BE FOR YOU TO LOOK OUT AT AN AUDIENCE AND SEE THE GEARS IN THEIR MINDS TURNING?

Yeah, basically. When you feel audiences reacting to what you're doing and they're laughing, like laughing hysterically, out of control, or just if a couple people go off the deep end and can't stop laughing, it's a really nice thing.

Laughter, in a weird way, is kind of like an orgasm to a certain extent. Being funny is this ability to kind of give joy to people, or realizations to people. It's a nice release for everybody. It's a release for the comedian because they're like, 'oh, Ok well I'm funny. What I'm doing is funny.' Then I get to laugh and forget about shit for a little bit. It's nice.

IT'S KIND OF KIND OF A CLICHE, THE IDEA THAT COMEDY COMES FROM A DARK PLACE. IS THAT SOMETHING YOU SUBSCRIBE TO?

I love mixing in really dark, weird stuff into what I'm doing. But I'm not really one of those people who comes from a dark sensibility or a life that I've had that's been kind of dark. It's mostly that I see ridiculousness in all things and you can create ridiculousness in potentially dark situations.

I READ IN THE NY TIMES THAT YOU WERE ON A QUEST FOR $1 MILLION IN THE NEXT TWO YEARS IN "PURSUIT OF WIDER TECHNOLOGICAL AMBITIONS." HOW'S THAT GOING? AND CAN YOU EXPLAIN WHAT THOSE TECHNOLOGICAL AMBITIONS ARE?

It's definitely true. I'd like to gather the resources to try out things technologically. Most of it's just sound stuff, just like being able to create great sound in a room, holographic sounds, imagery. Visual elements as well. experimental film techniques. Basically I want to create a laboratory to just exercise ideas that I'd like to experiment with.