Like a lot of comedians, Gabe Dinger knew from an early age what he wanted to do with his life.

He wanted to work at Blockbuster.

A miserable student—he ditched class so much he got sent to an alternative high school in "almost Gresham," near where he grew up—Dinger dropped out his senior year to live the dream of generous overtime pay and five free rentals per week.

"I was making more money than my teachers were," he says. "I was kind of like, 'Why do I need school? I love working here. I'll become a district manager. Boom! I got the job thing figured out.'" Somehow, though, that plan didn't quite work out. After a few years, he got fired on a "technicality."

He kind of, sort of, stole the store's copy of the Beverly Hills Cop trilogy. "I was devastated," Dinger says. "I had dropped out of high school to work at this place!"

Left floundering at age 21, he found his way to comedy soon after. It's a wonder someone with the name Dinger—"a German word that means 'whimsical erection,'" as he puts it—didn't realize his true calling sooner. He always knew he was funny, but only because he had to be. It was a defense mechanism, a way of deflecting taunts aimed at a kid who, well, has a euphemism for an erection as his last name.

It took a dare to get him onstage—from another comic he drunkenly heckled at a Beaverton open mic—but the moment of clarity hit him immediately.

"I remember grabbing the microphone, finishing that first line and getting that laugh, and it was almost like everything stopped," he says, "and I was like, 'Oh. This is why I'm Gabe Dinger.'"

A decade later, Dinger, 32, still looks more like a teenage video-store clerk than a grizzled standup vet. He's grown a mustache, but it can't hide his baby face—or, as he calls it, "nice-cop face"—and his squinted eyes make it seem like he's at least a little high all the time, which usually has a 50-50 chance of being true. It's a look that fits his comedy: casual and conversational, like a guy you end up talking to on the MAX, or who keeps you hanging around the counter at the convenience store after you've already made your purchase.

In truth, Dinger is about as "old hand" as Portland comedy gets. He's a regular at Helium and Bridgetown, neither of which were around when he started. He went on the road early, and learned how terrible it is touring the Midwest in the winter. (He took up improv so he could stay home during the cold months.) He's played prisons and old-folks homes, and an amateur cage fight in Kelso, Wash., along with such rites of passage as Sketchfest and Bumbershoot. He's shared martinis with Bob Saget, and got "the talk" from Norm Macdonald.

And yet, if you ask Dinger, it wasn't until recently that he actually figured out what the hell he's doing.

"I probably didn't start liking my comedy until four years ago," he says. His early material was almost exclusively about masturbating, because "that's the only honesty you have at that age." The first bit he felt had any worth was about his black stepfather making him watch Roots, and how for years afterward he couldn't watch Reading Rainbow without crying. "That joke alone kept me going for the next three years," he says, "until I wrote another joke that was kind of on that same level."

The jokes come easier now. These days, a lot of them are about Portland—specifically, how much better it is today than when he was a kid. He points out that the city used to be overrun with neo-Nazis, and suggests some "historic" homes are better off being demolished. "The house I grew up in was built in 1908," he said at a recent gig. "It was more spider than house."

"I want to make people not feel like shit for moving here."

GO: Willamette Week's third annual Funniest Five Showcase is at Alberta Abbey, 126 NE Alberta St., on Monday, Nov. 30. 7 pm. $5. For tickets, visit bit.ly/wwfunniestfive.

ezgif.com-crop