Every year—world-changing catastrophes aside—there's always at least one new comedy festival in Portland. The town is ripe for it. And while the entertainment ecosystem is slowly building back better, one festival that looks particularly promising is Rip City Comedy Fest.

The brainchild of local booker Joe Bukowski and stand-up James Bosquez, Rip City unfolds May 4-6 and promises a wealth of interesting comedy names, like Amy Miller, Blair Socci, Curtis Cook, AJ Wilkerson, Pallavi Gunalan, and pro skater turned podcaster Jason Ellis. There's also a night of unreleased video from Lance Bangs on the schedule—that you will not want to miss. 

Spread across four neighboring Southeast Portland venues—the Get Down, Funhouse Lounge, Rogue Eastside Brewing, and Helium Comedy Club—Rip City both spotlights screwball local showcases and invites some equally inventive ones from out of town.

The upstart fest presents an opportunity to see performers work traditional stand-up material—perhaps supporting Miller's Live! show (Get Down, Fri 9:30 pm) or on Curtis Cook's Best of the West (Helium, Sat 4 pm)—then pivot into a totally different creative mode for the more gameshow-like events.

"You're not just gonna do your stand-up, you have to be able to riff," Bukowski told the Mercury.

For instance, you could see your favs interrogated about things Kate Murphy and Ben Harkins found from Googling their names on the Weird Show (Rogue, Sat 6 pm).

Femmes the Rules (Rogue, Thurs 7 pm) is a show hailing from LA where a woman or non-binary comedian monitors a cis man comedian during his set and may assign arbitrary rules he has to follow. Imagine your average dude comedian having to refrain from discussing his wife or girlfriend—sounds delicious

Everyone Hates You (Get Down, Fri 11:59 pm) promises to emotionally scar comedy guests Nariko Ott, Courtney Byrd, Jordan Casner, and Devi Kirsch as they roast battle one another. Eventually, one battered champion stands to face the might of the show's hosts, local devastators Bryan Bixby and Tory Ward. 


Though in its fledgling year, every show on Rip City Fest's schedule has a name you want to see or juicy premise, promising "oh snap" ramifications. That's due largely to the combined comedy scene knowledge of the fest's planners.

"He knows a lot about the planning side, and I know a lot about the comedy side," Bosquez said of his collaboration with Bukowski. A great local comedian in his own right, Bosquez was one of this year's Undisputable Geniuses of Comedy. He also hosts a semi-regular show at Helium called the Transplants, which spotlights excellent comics who just moved here. "Transplants notoriously don't get as much stage time," he explained.

The self-deprecating Bukowski described their partnership as "a couple of servers from Helium Comedy Club—just doing their own thing" then slowly revealed a long history of his own event management: years interning on the Vans Warped Tour street team, managing a Roller Derby team in St. Paul, and recently starting up a side hustle of planning shows for comedians he liked. "I'm just a guy with funny friends who wants to help them do shows in a fun way," he said.

When the two began to plan the festival, Bukowski applied a liberal amount of DIY elbow grease. "I drove around to different venues," he said. "I just went over and talked to them, instead of waiting for an email."

"That's how he got a lot of sponsors," Bosquez pointed out. Among others, New Deal Distillery and nearby bar the High Dive signed on to support.

The venues, which are all semi-walking distance from one another, are mostly places Bukowski has booked at before. Rogue is where he first started putting together bills in Portland. Helium is the main day job for both he and Bosquez. The Get Down is where they first put on a non-Helium event. 

"It actually works for a comedy show," Bosquez said of the Get Down. "The ceilings are lower. Good views from everywhere. Also, it feels like a secret place. If you walk past it, you wouldn't even know it's there."

Rip City's schedule of 13 shows feels ambitious for its first year, but Bosquez and Bukowski described the momentum build, which grew as they planned. More guests wanted to jump on. Those names brought others.

One of the festival highlights is definitely Lance Bangs Presents (Get Down, Sat 6 pm), which promises unreleased footage from the filmmaker's vault and stand-up from Miller, Casner, Shain Brenden, and others. As a filmmaker, Bangs has shot music videos for an exhaustive list of your favorite musicians and that work is easily eclipsed by the comedy specials he directed for your favorite comedians, but he's most commonly associated with Jackass. So unreleased footage? Yeah. You want to see that.

And nothing beats the Rip City closer: Miller's irreverent Midnight Ma$$ (Funhouse, Sat 11:59 pm). Some will fondly remember the show from its Portland days; the format is loosely organized around Catholic mass structure, with the wry Miller (who grew up fundamentalist Christian) presiding over a court of dynamic fellow comedians.

"Having that as the last show is so cool," Bukowski said. "The romantic in me really wants to connect the new comedy shows happening now with the old shows that inspired this generation of comics."

Rip City Fest will be held at the Get Down, 615 SE Alder; Funhouse Lounge, 2432 SE 11th, Rogue Eastside Brewing, 928 SE 9th; Helium Comedy Club, 1510 SE 9th; May 4-May 6. Schedules, tickets, and weekend passes can be found at ripcityfest.com.