PEACE OUT: Portland’s Funniest Person Steven Wilber.
IMAGE: Daniel Cole

Over the past few years, Portland has grown into a hotbed of standup comedy nights, but it still doesn't have the paid gigs needed to carry a large roster of working comics. For that, there are basically two choices: Los Angeles or New York City. Already, stalwarts like Ron Funches and Ian Karmel have departed to Southern California for a network television sitcom and late-night writing gigs, respectively. Shane Torres, Portland's Funniest Person in 2013, chose New York.

Now, Steven Wilber—winner of Portland's Funniest Person 2014 and a previous WW Funniest Five comic—is following the trend and migrating to Los Angeles in October. Last month, he visited the City of Angels and almost didn't come back. "But I wanted to have a goodbye show," he says.

Before his big sendoff this Thursday, Wilber told Willamette Week what he really thinks about Portland comedy.

WW: Los Angeles is a pretty big move.

Steven Wilber: It's scary. I'm feeling better about it now, but you're always afraid that you'll go down there and instantly you'll be peeing in a bag on the streets or something.

Have you already done work in L.A.?

The first time I went was September or late August of 2014, shortly after I won the [Portland's Funniest] contest. And then I went down in April of this year. [I do] the same type of shows there that I do in Portland, like a small black-box theater or a bar.

I think meeting people at festivals, like people who come up for Bridgetown, helps because everybody runs a show down there. If you know enough people, at least you can get some stage time. It's much easier to get your foot in the door with somebody who knows you, rather than just cold-calling people, and it just springboards from there.

Are you going down there with a job in hand?

No. I'm just using the "heat" that I got from doing Just for Laughs [in Montreal]. I was told that if I stayed in Portland, that good will would sort of fade away. It's a good time—I don't have a job, or a girlfriend, or a lease. It's a good time to cut and run if you have to.

You were named a "New Face of Comedy" at Just for Laughs this year. Has that put more pressure on you?

When I move to L.A., I'm definitely going to feel the pressure of trying to keep afloat in this sea of talented comedians. The fears are like, where am I going to live, how am I going to eat, and will I just get lost in obscurity down there?

I felt a lot of pressure that whole year [after winning Portland's Funniest Person]. It's like you are calibrating the audience to have this expectation, and they're like, "We'll see about that," and I hated that. It was a great opportunity. It helped me get into festivals and stuff, but I hated the pressure.

What was comedy like in Portland when you got here?

I didn't start until 2011. I didn't know there was comedy here, and I think at that time there really wasn't. There was Augie Smith, and I think Gabe Dinger was around.

I did it as a personal challenge to myself. I went to school for film, but I also liked making comic books and cartooning and writing. I was just in a real funk, and standup is like the scariest thing. I was like, if I could do that I could do anything. The first open mic I did was Boiler Room.

Do you feel like the scene here is good for developing young comics?

There's its share of in-fighting, or little clique behavior, but nowhere near some of the other scenes I've witnessed. I think Ian [Karmel] and Ron [Funches] and Sean [Jordan] and Shane [Torres] and Bri [Pruett]—all these people who I looked up to when I was starting—they were so great and nice, and just not dickheads to younger comics.

Portland is a good incubator for talent. It's open to weird stuff. It's open to whatever type of standup you want to do. You're not going to get swept up in politics. And you can get onstage for five minutes almost every night of the week.

How did other local comics react when you announced you're going to L.A.?

A lot of congratulations. It's weird to be congratulated for going to sleep on an air mattress in a guy's living room.

SEE IT: Kick Rocks, Steven Wilber!: A Comedy Good-Riddance Show is at Hollywood Theatre, 4122 NE Sandy Blvd. 9:45 pm Thursday, Sept. 24. $10.