Three years ago, Steven Wilber was worn down. He was stuck in an uninspiring administrative job at a collection agency and felt short on creative motivation. So he made himself a promise: seven open-mic nights.
"The idea of standup has always been the scariest thing," says Wilber, 31. "Because it's just you up there, it's all written by you, and you're getting criticized every sentence, instantly. If I just went to open mics and did terrible, then I could do anything."
So he hit the Boiler Room in Old Town. He asked the audience if anyone was unsure whether they were a redneck. He followed with a joke about his dad's penis. He told the story of a sex talk gone awry, which led to his belief that babies come out of a woman's pajamas.
And much like pregnancy—"I have a lot of jokes that involve babies," he says. "And the making of"—once was all it took. He was hooked.
"I was just like, 'OK, I like this,'" Wilber remembers. But then he checks his hubris. "I wish there was a tape or something, because up there I feel like I did OK. I can't imagine that I actually did OK. I feel weird telling people I killed."
As a naturally jokey person, he found standup a good fit. "Some would call it a character flaw," he says. "It's something people have said in the past: 'You're never serious. Can't you just be serious with me? I'm leaving.' That sort of thing."
Wilber grew up in Pomeroy, Wash., a small town in the southeastern part of the state. Pomeroy had no stoplights and consisted mostly of hyphenate businesses—a pizza parlor-laundromat, a pharmacy-RadioShack. Due to its small size, the town also had hyphenate cliques: stoner-nerds, nerd-jocks. Wilber says he was "the poor kid, the smelly kid."
"If I was funny," he adds, "then people would want me around."
His parents had worked as carnies before Wilber was born. "My dad was a pipe fitter, whatever that is," he says. "That might just be a term for gigolo that I'm just realizing now."
He moved to Portland by way of Spokane in 2008, drawn by the bright lights of what a friend's mother said would be the next Hollywood. Things haven't been quite that glamorous for Wilber, who still works an office job and has his sights set on Los Angeles. But he has found standup success here, with awkward rapping and singular mnemonic devices for remembering presidents or the planets. Onstage, he recalls an unassuming high-school history teacher, mildly animated but non-threatening.
In one bit, he expertly deconstructs a recent TriMet safety campaign. "There's [an ad] that says, 'Don't let LOL become DOA,'" he says. "And there's one that says, 'Don't let death metal become death by metal.' And there's one that says, 'Don't let Candy Crush become your body crushed by the weight of a train.'… But my favorite of these ads is one that says, 'Don't let your love for the band Train...become public knowledge.'"
Back in July, these jokes earned him the crown in Portland's Funniest Person contest at Helium Comedy Club. The offers, Wilber says, have been rolling in ever since.