The Unstoppable Funniest Five

Funniest Five 2025 (Nathaniel Perales)

Here are Portland’s funniest five comedians, according to their peers.

The country’s a circus, under new management from the carnival barker-in-chief. There’s just one thing to do: Send in the clowns.

Comedy as we know it goes all the way back to the vaudeville tents where some of television’s foundational comedians—the Three Stooges, Milton Berle and William Frawley among them—rubbed elbows with contortionists, cabaret dancers and sideshow spectacles. Sure, George Carlin convinced a generation that comedy should reflect truth, but sometimes the truth is so strange it sounds like fiction.

For example, Ally J. Ward’s sex-positive humor once landed her in a more adult version of the “two prom dates problem.” While Ward was performing as the token woman on an otherwise all-male lineup, who should pop up in the audience unexpectedly but both of her dominatrixes? Ward worried what would happen to her until she learned how the dommes bonded over brainstorming ways to humilate her.

“When I asked them if they thought of any new punishments for me, they told me watching all those men perform comedy was punishment enough,” Ward says.

This year’s Funniest Five comedians in Portland, chosen in our annual poll of more than 100 comedians and show producers, have embraced the ridiculous. Each is distinctive in style and delivery, but have things in common. They’re all students of the past 35 years of standup—Maria Bamford and Patton Oswalt, come get your kids—without absorbing any mean streaks. They take comedy seriously as an art form, even if their approaches to their crafts are different. After all, comedy is a big tent.

If he hadn’t gone out to open mics, then Rachelle Cochran and David Tveite might have completely different lives. Tveite pursued poetry before he was on Last Comic Standing, and Cochran attended Catholic school near the Oregon Country Fair and seems to have found herself through comedy. Will Lampe and Lee H. Tillman could have retired during the pandemic but kept telling stories. And if Ally J. Ward let shame hold her back, she wouldn’t have been named Portland’s Funniest Person.

None traveled the same road to the stage, but all started on their comedy journeys and kept going even when there were offramps to quit because they felt they needed to make people laugh. What they riff on and skewer at Revolution Hall on Feb. 7 is still anyone’s guess, but one thing’s certain: Even if these comedians don’t let you forget your troubles, they’ll seem less daunting after you’ve laughed about them. —Andrew Jankowski, Assistant Arts & Culture Editor

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