2026 Gambit Brewing Funniest Headliner Contest: Prelims Week 1 (June 2nd)

Join us for the 2nd annual Gambit Brewing Funniest Headliner contest, featuring 20+ professional standup comics battling it out over 3 weeks for a $1,000 grand prize. The best part?? YOU decide who advances and who wins!!

Prelims are free admission ($10 donation at the door suggested) and take place on June 2nd and . The Top 3 scores from each night will advance to the , where audience members will use electronic scorecards to determine the winner of the $1,000 prize! Join us each week and don’t miss your chance to be a part of Twin Cities comedy history!

See the full lineup of comics for June 2nd, including headhosts and bios, below!

* has established itself as a go-to destination for standup comedy in Lowertown St Paul, hosting Friday Night Comedy shows; the Funniest Person in St Paul and Funniest Headliner contests; a weekly open mic; plus a variety of themed shows (e.g. Pride Comedy Night, Valentine's Dinner + Comedy, NYE Comedy, fundraisers, and more). Find out why our audience members are calling Gambit “a cool, unique room” with “chill vibes and good beer”, “fantastic friendly staff”, “great comedy”, and “incredible talent” (quotes from audience feedback forms)!

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Host or Publisher Jesse The Shrink