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Portland has a new funniest person in town, at least according to Helium Comedy Club.
Ian Yearsley, 25, took the trophy at Helium’s annual Portland’s Funniest Person competition on Aug. 30. He won the title and a $3,500 grand prize, taking out about 250 fellow Portland comedians over three rounds of competition.
Yearsley moved to Portland from Boise, Idaho, last June and has been doing comedy for about five years. This was his first competition in Portland. (Not to be confused with WW’s annual Funniest Five competition, which is chosen through a poll of local comedians and show producers. The reigning champ is Andrea Menchaca.)
Yearsley got the big win with topical jokes, he says, focusing on “politics, sex and drugs.” He’s originally from tiny Crouch, Idaho (population: 154), so he gets a lot of mileage off of jokes about the rural versus urban experience.
“I try to talk about heavy subjects but give a lighter take on them,” Yearsley says. “I don’t like to be really dark; I like to do a bait and switch a little bit.”
Since living in Portland, Yearsley’s favorite comedy mics have been at McMenamins’ Al’s Den, Haymaker, Yamhill Pub and Laugh Basement at the Goodfoot.
Yearsley is succeeding Jordan Casner, Portland’s Funniest Person of 2025. Yearsley’s fellow finalists were Brenden Creecy, Cody Chasteen, Kate Murphy, Skylar King, David Tveite, Grant Leavitt, Cimberly Nickell and Eugene Kailiuli.
Helium is a national chain of comedy clubs. It launched the Philly’s Phunniest Person competition at its Philadelphia location in 2005 to celebrate local talent.
Yearsley says he owes his win to having confidence in himself and his set.
“Confidence, but not in a ‘knowing you’re going to win’ way,” Yearsley says, “but knowing that your set is just about you, and not getting psyched out by who just went before and who is going after.”
