Friday Night Comedy! with Steve Gillespie at Gambit Brewing in St Paul

Join us for this special upcoming edition of Friday Night Comedy! at as we're bringing in national headliner , who's released three Top-10 albums, appeared on Conan, was named a finalist on CMT’s Next Big Comic, and has opened for such big names as Dave Attell, Tom Segura, and Gilbert Godfried.

Also joining in on the fun will be Twin Cities favorite Shyloh Blake, who recently finished 2nd place in the 2025 Funniest Person in St Paul contest. Shyloh is known for telling funny stories about navigating life’s awkward moments…which for her are most moments! She was highlighted in the “Next Up On Stage” series on MNComedy.com which noted, “Her quick wit and warm delivery make Blake an instant hit!" She was also a finalist in the Funniest Person contest at MOA's House of Comedy!

Host and producer is a bona fide licensed therapist and standup comic who gives audiences a sneak peek into the inner-workings and often hilarious experiences of a mental health professional. He's co-founder of and produces shows as well as .

Here's what previous audience members are saying about Gambit Brewing Friday Night Comedy shows:

"Cool, unique room. Great talent!"

"Great comedy! We'll be back!"

"Love the comedians!"

"So fun! Want more."

"Super fun, comic variety is great, friendly environment!"

"Hilarious!!! A must see!"

"Good flow, headliners were great."

Gambit serves up fresh, delicious food and drink options. In addition to their assortment of award-winning craft beers, they also offer up seltzer cocktails, housemade root beer (hard or N/A), THC Fruit Punch, N/A beer, and more. They also bake their own gourmet pizzas (you gotta try the Curd is the Word - pepperoni + cheese curds!), craft hot dogs, empanadas, and a giant Bavarian pretzel. Munchies for sale included a dessert pizza, cookies, and popcorn!

Get your tickets now and we'll see you at Gambit. 🎤😂 🍻🍹🍕🌭🥨

Also check out other Comedy events in Saint Paul, Contests in Saint Paul, Entertainment events in Saint Paul.