Kickstand Comedy’s improv teachers have a collective 70+ year of improv experience—from performing at theaters and festivals across North America (Austin, Minneapolis, New York, Chicago, Los Angeles, Toronto, Vancouver BC, etc) to learning at countless schools (Annoyance Theater, Neo-Futurists, The Liberators, Upright Citizens Brigade, iO, Huge Theater, Comedy Sportz, Brave New Workshop, Second City, ColdTowne). We’ve brought the joy and skills learned in class to advertising, restaurants, sign language interpreting, website design, superficial conversations, deeply intellectual conversations, intensely dumb conversations, Nike, pinball throwdowns, TV (IFC’s Portlandia, TNT’s The Librarians), professional DJ gigs, commercials, and bipartisan Thanksgiving dinners. We’ve learned from a murder’s row of improvisors including Will Hines, Susan Messing, Rebecca Sohn, Rich Sohn, Noah Gregoropoulos, Dina Facklace, Larry Arrick, Mick Napier, Laura Doorneweerd, Joe Bill, Bill Arnett, Mike Fotis, Carla Cackowsi, Craig Cackowsi, Jill Bernard, and tons more.

We’ve got tons of improv and life experience for you to lean on and glean from.

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Craig McCarty


Eric Simons

Adam Trabka

Janet Scanlon

Jeff Kelsay




Dylan Reiff is an improviser and creative living in the dream boat city of Portland, OR. Dylan began his improv career after moving to Chicago to study and perform experimental theater with the Neo-Futurists. In the late 00's he began studying improv with the Annoyance Theater. Since Chicago he has studied with The Liberators, Upright Citizens Brigade Theater, and has been lucky enough to take workshops from improv royalty such as Will Hines, Susan Messing, Rebecca Sohn, Joe Bill and many more.

Reiff is the co-founder of Kickstand Comedy Space and a member of indie teams TUNNEL (Stumptown Improv Festival, Out of Bounds Comedy Festival) and Biz Caj (Friday Night Fight Grand Champion).

He has been coaching and teaching in Portland since 2014 and can't get enough of it.