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Kickstand Comedy co-founder Dylan Reiff has watched some of his hilarious peers’ careers balloon from local humor staples into career professionals employed by some of entertainment’s biggest names. But for his group’s own success, he’s surprised that what started as a DIY space a decade ago in the basement of a Hollywood District bicycle shop would not only survive the pandemic and an earlier city-ordered shutdown, but thrive in a building all its own.
“It’s a really cool thing to see a community continue to grow and change and evolve,” Reiff tells WW via telephone. “I am blown away that it’s grown into what it is. It’s a very cool thing to see a DIY space turn into a community space that’s still really thriving.”
The nonprofit comedy venue and education center celebrates 10 years strong with a slew of shows that began Nov. 30 and will wrap Dec. 21, both at Kickstand Comedy’s venue on Southeast Hawthorne Boulevard and at the Clinton Street Theater. For instance, the Mega-Aardvark—a super-sized edition of regular improv show The Secret Aardvark hosted on Thursday, Dec. 12—saw Kickstand attempt to break a record for most improv comedians on one Portland bill. It’s not clear what the record was before the show, but Reiff says 115 comedians performed together in around two hours’ stage time.
“It’s cool to have a place where all those types of performance can come together,” Reiff says. “As an improviser, it’s fun to watch standup, and as a standup, it’s cool to watch improv and see how those different tools can cross-train or what serves you and how you want to grow. It’s been cool to have a hub.”
The Clinton will host two shows on Friday, Dec. 20, while Kickstand headquarters will also host two on Saturday, Dec. 21. Holy Shit Improv at 7 pm will feature Los Angeles comedians Casey Feigh, Rekha Shankar, Ronnie Adrian and Will Hines alongside house troupe the Kickstand Cvlt. The 9 pm show, Earthquake Hurricane, was Kickstand’s first-ever standup show; see original players-turned-hometown legends Alex Falcone, Bri Pruett, Katie Nguyen and Anthony Lopez return to share the stage with Imani Denae, Steven Wilber, Ben Harkins, David Seung and Kirsten Kuppenbender.
“It’s a real testament to the vibrancy of Portland comedy,” Reiff says. “We are here because both performers and audiences have believed in the mission of creating undeniable Portland comedy.”
On Saturday, Shankar and Adrian will host Kickstand’s BIPOC-focused series Mosaic Improv featuring Naomi Dixon, Breezy Núñez-Webb, Mary C. Parker, Eric Simons, Chris Williams and August Wygal at 7 pm. That night’s 9 pm show, Hi(nes) I’m(prov) to Meet You—Reiff knows this title is a tongue twister—casts Will Hines in a real improv class for fake students, which have previously been characters like William Shakespeare and Batman. Reiff credits the rising popularity of improv performances to podcasts, particularly those focused on Dungeons & Dragons.
“Comedy is undeniably better when you have more personalities and perspectives, and historically there have been a lot of voices that were left out, so our mission is, how can we keep either—whether that’s a cost barrier or gatekeeper barrier, how do we get more people involved in comedy and how do we help give them the tools so they can make the most out of expressing those ideas?” he says.
The pandemic stopped Kickstand from taking over the Old Town venue that once held the Brody Theater, but the comedy- and improv-focused venue now operates blocks from Helium Comedy Club, creating a humble humor hub off of Hawthorne. As of September, Kickstand has spent a full year in the building that once held British footballer pub Toffee Club. Reiff says Kickstand started as a way to help get people into comedy. The goal for the next 10 years is for Kickstand’s management to buy the building. Reiff is stepping away as Kickstand’s artistic director, instead onboarding Kickstand’s new executive director, Paul Stein, who comes from HBO and Comedy Central. Reiff isn’t running right out the door, but he’s admittedly excited for the next era of Kickstand without him.
“He’s kind of the missing piece we’ve always needed to help bring us into this next decade,” Reiff says of Stein. “It’s fun to close a chapter of the first 10 years—can’t believe that actually happened!—and to have a lot of hope for what’s to come, it’s a cool place to be and I’m really stoked.”
SEE IT: Kickstand Comedy 10th Anniversary shows at Clinton Street Theater, 2522 SE Clinton St., 971-808-3331, cstpdx.com.; and Kickstand Comedy, 1006 SE Hawthorne Blvd., 503-719-5685, kickstandcomedy.org. Clinton: 7 and 9 pm Friday, Dec. 20. $20–$25. Kickstand: 7 and 9 pm Saturday, Dec. 21. $20–$40.