Freshly Squeezed Comedy New Year’s Eve with Wendy Maybury at Gambit Brewing – Saint Paul, MN

Congrats, your quest to find the perfect New Year’s Eve plans has been completed!! (high-five) Gambit Brewing is one of the most popular destinations in Lowertown St Paul & for good reason: the vibe is unmistakeably chill yet fun; their award-winning, hand-crafted drinks include beers, hard seltzer cocktails, & hard root beer; & their unique variety of gourmet pizzas (pepperoni & cheese curds, anyone??) were recently hailed by the St Paul Pioneer Press.

And then there’s the comedy! Gambit has quickly established itself as a premier destination for live standup comedy in St Paul. Whether it’s their popular Friday Night Comedy shows, St Paul Art Crawl Comedy Night, annual Funniest Person in St Paul contest (featured in the Minneapolis Star Tribune & Pioneeer Press), or weekly Tuesday open mic, audiences have been responding enthusiastically. Here’s what some of our audience members have been saying:

“Cool, unique room. Great talent!”

“Super fun! Friendly environment!”

“Great! Chill vibes & good beer.”

“So FUN! Want more.”

“Hilarious!!! A must see!”

“Amazing, let me know about the next one!”

“Everyone was f***ing great!”

“Very funny. VERY good.”

On New Year’s Eve Gambit welcomes Freshly Squeezed Comedy, the high-energy, wacky standup duo of Lefty Crumpet & Jesse The Shrink. They book, produce, & perform in their own shows throughout the state of Minnesota. Lefty brings his silly songs & Jesse brings his unique perspectives as a licensed therapist (yes he really is a shrink & yes, that probably means he’s analyzing you!).

Joining them for these special holiday shows will be recording artist & headliner Wendy Maybury, whose debut album “She’s Not From Around Here” hit #1 on the Amazon, iTunes, and Spotify Comedy charts. And Funniest Person in St Paul finalist Aron Woldeslassie will also make an appearance!

Whether you want to celebrate early & be home by 10pm or live it up & ring in the New Year at midnight with us (free glasses of champaigne-flavored hard & N/A seltzers will be served to toast with!) we’ve got you covered. 7:30pm or 10pm show, $20 Early Bird tickets or $30 VIP tickets (with preferred seating)…we’re giving you options. Check out the bios of our comedians below & then grab yourself some tickets! Don’t be that person who waits ’til New Year’s Eve – only to find out there’s no tickets left!!

ABOUT OUR COMEDIANS:

Wendy Maybury

Meet Wendy Maybury, a Southern belle from the heart of Dixie who has taken the comedy world by storm. Wendy is a single mother who balances raising her kiddo with a successful standup comedy career. Her relatable experiences as a single parent, combined with her quick wit & Southern charm, have made her a hit with audiences everywhere. Whether she’s sharing stories about her dating experiences or simply observing the world around her, Wendy’s comedy is a mix of humor and heart that leaves audiences in stitches. So sit back, relax, and get ready to laugh along with this hilarious single mom from the South!

Jesse The Shrink
What do you get when you mix a shrink & comedian? This guy! Jesse is a bona fide licensed therapist & standup comic who gives audiences a sneak peek into the inner-workings & often hilarious experiences of a mental health professional. Whether he’s talking about navigating virtual therapy sessions during an apocalypse or just trying to figure out what to tell drunk people he does for a living, one thing’s sure: after hearing his stories you’ll never see therapy (or your therapist) the same again!

Jesse is the producer & host of Jesse The Shrink’s Midlife Crisis Show, the St Paul Comedy All-Stars Show, Friday Night Comedy at Gambit Brewing, the 420 Standup Comedy Show, & the St Paul Art Crawl Comedy Night. He’s also co-founder of Freshly Squeezed Comedy, founder of the Funniest Person in St Paul contest, & runs a weekly comedy open mic at Gambit Brewing. Jesse was a 2024Funniest Person With A Day Job finalist at House of Comedy in Mall of America & has been a guest on the KQRS Morning Show & Tom Barnard Podcast.

Lefty Crumpet
Lefty is a 25-year-old, Minneapolis-based, ethnically-ambiguous, joke-slinging, musical funnyman with social anxiety from Riverside, California. He started doing standup comedy in college & immediately fell in love with the stage. His love of playing music led him to begin incorporating comedy songs into his standup performances. He lifts your hearts and minds with absurd and hilarious jokes and tunes, about various topics ranging from relationships to Doordash.
Lefty was a finalist in the Funniest Person With a Day Job contest at Rick Bronson’s House of Comedy in Mall of America & is co-founder of Freshly Squeezed Comedy. You can find him bringing joy and confusion to crowds all over the Midwest.

Aron Woldeslassie

Aron is a standup comedian, author, and producer based in St. Paul. His comedy comes from a blend of observations on race, relationships, and culture as well as personal stories.

He was featured in the St Paul Comedy All-Stars show and has been a finalist in numerous comedy contests, including the Funniest Person in St Paul (Gambit Brewing), Funniest Person in Minneapolis(Sisyphus Brewing), and Funniest Person with a Day Job (House of Comedy in Mall of America). Aron is also a founding member of The Nordly and Minnesota Tonight and his work has been featured on Minnesota Public Radio, TPT’s Almanac, Mpls/St.Paul Magazine, and other various literary magazines.