Portland is a city where you can find a drag queen hosting a screening of Singin’ in the Rain at the art museum, a weekly comedy showcase in a Southeast Portland clown-themed bar at midnight, and an improv theater in NE that’s been doing shows every Sunday for years without anyone outside a three-mile radius catching on. This is a comedy city. It has always been a comedy city. It just does its comedy the Portland way. locally, independently, and just slightly off the main road.
In 2026, some genuinely large names are putting Portland on their tour routing, and the Arlene Schnitzer Concert Hall. the beautiful downtown venue everyone just calls “the Schnitz”. is where most of it lands.
Chelsea Handler Opens the Season Right
June 12 at the Schnitz: Chelsea Handler brings The High and Mighty Tour. Handler is having a real career moment. simultaneously sharper and more relaxed than she’s been in years, and her current live show reflects that. Portland audiences, who according to Willamette Week have a documented preference for comedians who don’t sand down their edges, are the right crowd for her. The Schnitz is the right room. Plan accordingly.
August: Ali Wong Comes to Town (Twice)
The summer highlight is almost not fair. Ali Wong. who is currently operating at the intersection of stand-up celebrity and genuine cultural moment. is playing Portland two nights in a row at the Schnitz. Friday, August 7 and Saturday, August 8, both at 7 PM. Her official tour page already flags Friday as “Few Tix Left,” which means the window is closing faster than you’d think. If you’ve been telling yourself you’ll catch Ali Wong the next time she comes around: this is the next time, and Portland is getting two nights of it.
Tickets are available now for the Saturday show. That one is not background noise. It is, by the general consensus of everyone who has seen her current tour, worth it. She is performing at the peak of her powers right now, and that’s not nothing.
Fall: The Moda Center Gets Involved
September brings Josh Thomas to the Newmark Theatre on September 18 with Jiggle, Jiggle. Thomas. Australian comedian, creator of Please Like Me. has a specific and intensely devoted following. People find him through the show and never really leave. His live performances have the same quality as his TV work: funny in ways that occasionally catch you off guard.
October is when Portland comedy scales all the way up. Matt Rife brings his Stay Golden World Tour to the Moda Center on October 10. This is arena comedy at full volume. Rife’s audience is enormous, devoted, and loud in exactly the way an arena crowd should be loud. If you’ve only seen clips online, the live version at the Moda Center is a different thing entirely. One week later, Daniel Sloss plays the Newmark Theatre on October 18 with his BITTER tour. Smaller room, completely different energy, no less worth your time. Then the month closes with Laura Ramoso at the Schnitz on October 22 for The Calm Down Tour. Ramoso is one of the fastest-rising voices in stand-up right now. A good time to see her before the venues get bigger.
November: Something Small and Wonderful
The year ends at a completely different scale. Davide De Pierro at the Alberta Rose Theatre on November 4. The Alberta Rose is a 350-seat room in NE Portland. exactly the kind of venue Paste Magazine’s Portland comedy guide was writing about when it described the city’s love of non-standard spaces. De Pierro in this room is the show that sells out quietly and gets talked about afterward.
Everything above is at ComedyCalendar.com.
