wo years ago, comedian Gabe Dinger placed third in Portland’s Funniest Person contest at Helium Comedy Club. Last year, he was second. This year, everyone told him it was his time.

He placed third.

"After the competition, I got so many messages from people as if a family member had just died," Dinger says. "They were like, 'Hey, are you OK? How are you doing?'"

Dinger claims he felt quite all right. He may not have earned the crown, but he figures a trilogy of top-three finishes at least makes him the MVP of Portland comedy. It's a role that Dinger, with his low-key but nimble observational standup, has played for a while. A Portland native who grew up on Southeast 122nd Avenue with a motorbike-riding dad and a churchgoing mom who predicted The Simpsons would fail ("she has a very bad barometer for comedy," Dinger says), he's been doing standup in this city for nearly a decade. He's a fixture at open mics—he tries to hit three a week—and at Helium. He's appeared at the Bridgetown Comedy Festival since that now-venerable fest launched in 2008, and he's active in improv, performing with all-dude troupe Whiskey Tango. All of which makes the 31-year-old something of an elder statesman in a standup landscape crowded with wide-eyed newbies—some of whom, to Dinger's frustration, are in it more for the scene than the craft.

"There are a handful of people now who don't really want to do comedy," he says. "They like the idea of going to a bar and having a group of people be like, 'Hey, you're here!'"

Ten years ago, Dinger says the local comedy landscape was "the Wild West." Boozers jeered at comedians, who in turn threw things at the audience. Dinger fondly recalls the time Richard Bain aimed a Rice Krispies treat at a table of hecklers, only to have it land on a ceiling fan and fly off onto an innocent woman (she ate it). As a 21-year-old managing a Blockbuster store—he started working there while still a Risk-playing, pot-smoking teen—his first standup stint came at a comedy club in Beaverton. Attendance was sparse, mostly sots fueled by free drinks from the club's owner—"a pushover alcoholic," Dinger says. But with jokes about Valentine's Day, venereal disease and masturbation, he earned laughs.

"My first time went extremely well, which I think helped the next six months that went extremely terribly," he says. "When I look back now, I'm amazed I had the confidence to keep going."

Today, Dinger's standup has an easy assurance to it, with bits about how Portlanders treat the sun like a deadbeat dad and the occasional mildly scatalogical aside.

It's far removed from the material of his early career. Take, for example, the jokes he brought to the Oregon State Maximum Security Prison when he performed for a room full of orange-suited men with life sentences. "No one could pass a background check but me and one other comic. I was very green at the time. I was 23, and I looked like a baby," says Dinger, who still has the same youthful face and mop of dark hair. His most successful joke that day? That he looks like a lesbian from behind. "It makes me cringe thinking about it," he says. "It got laughs, but they were all in a very good mood. They were one of the most gracious audiences I've ever been in front of."

Unlike other once-local comics, Dinger says he has no interest in abandoning Portland. Life is good, he says: He works part-time at the cafe Crema, and he plans to record his first comedy album this fall.

"The whole idea that comics have to be brooding and upset and miserable in order to be funny, I don't buy that at all," he says. "I think comedy is based in frustration, not so much in misery, and I don't think any amount of happiness will ever take frustration away."