Lil Chuck Boston

05/29/2026

🩷 Holy S**t Improv features some of the best best comedy talent out of LA 🌴 Fast, funny, silly, smart and as consistently hilarious as any written show. So good, you won't believe it's improv!

The Holy S**t cast will be: Ryan Gaul, Corin Wells, Casey Feigh & Anna Bezahler

🗓️ Thursday, June 11 @ 7:30 PM
Get tickets at LilChuckBoston.com

Holy S**t Improv Lineup: Ryan Gaul, Corin Wells, Casey Feigh & Anna Bezahler Get Tickets Holy S**t Improv Holy S**t Improv features some of the best best comedy talent out of LA. The Holy S**t cast will be: Ryan Gaul, Corin Wells, Casey Feigh & Anna Bezahler Thursday June 11th | 7:30 PM Get Tickets

05/22/2026

The doctor arrives to the Lil Chuck! 🎤

Dr. Kojo Sarfo is a comedian, content creator, author, and mental health nurse practitioner with over 6 million followers, 150 million monthly views across social media platforms, and a mental health workbook featured on NBC’s Today Show. His work blends neurodivergence, mental health, and cultural identity into comedy that is equal parts hilarious and uncomfortably real. This tour is where the doctor finally takes his own advice and tells the truth!

Get tickets at LilChuckBoston.com

05/20/2026

Sober & Curious Boston is coming to the Lil Chuck!

is a nonprofit creating community and connection through events and experiences without the pressure of alcohol, welcoming anyone who is sober, sober curious, reevaluating their relationship with drinking, or simply looking for something different. All are welcome.

🗓️ Thursday, July 30, 2026 | 7PM
🎟️ Get tickets at LilChuckBoston.com

05/18/2026

🚨 Big Grande is coming to the Lil Chuck! 💜

Big Grande has been bringing their brand of rapid, honest, and wild live shows to sold out crowds around the country, hell, the continent, for over a decade. Join them for a show that leaves you laughing (hopefully) and them sweating (definitely).

Big Grande’s podcast, The Teachers Lounge, gained a fervent following on The Earwolf Network before they began selling it directly to fans. You can find it, along with their four episode live improvised comedy special, sketches, animated content, merch, and more at biggrandewebsite.com.

Individually, you’ve seen them on The Other Two, Brooklyn 99, Paranormal Activity: Next of Kin, Superstore, Comedy Bang Bang, Son of Zorn, Bless the Harts, Playing House, and of course, Last Call with Carson Daly – as well as behind the camera on Lights Out with David Spade and Netflix: After Party.

🗓️ Wednesday, June 10 | 7PM & 9PM
Get tickets at LilChuckBoston.com

03/23/2026

🔥Coming to Lil Chuck at the Charles Playhouse THIS WEEKEND: Alaire Thomas is a NYC-based comedian, podcaster, and content creator with 2M+ followers, known for her hit podcast Yap & Strap and relatable, feel-good content. Now she’s hitting the stage for her debut comedy tour, bringing real-life stories and big laughs.

🎤 Don’t miss it: March 26 | 7PM

03/23/2026

You’re invited to SlapSchtick’s third annual Passover seder! And by seder, we mean sketch and improv show themed around all things Passover! Come for the brisket*, stay for the comedic takes on everyone’s favorite Exodus story.

🗓️ Thursday, April 16 @ 7:30 PM
📍 Lil Chuck at the Charles Playhouse

“Matzah Mia: Here We Go Again” is a 90-minute 2-act show full of cutting-edge improv structures and brilliantly funny sketches that everyone will enjoy, regardless of religion or ideology!

The show is exactly one week after Passover ends (and exactly one day after your taxes are due), so you can't possibly have anything else going on! Join the cast of SlapSchtick at Lil Chuck on Thursday, April 16th, at 7:30 p.m. Moshe’s granddaughter sees all of our shows, plus your ailing Bubbe already bought tickets for herself, so the least you could do is come keep her company!
Grab your tickets before they’re gone!

*Brisket will sadly not be provided.

199-Seat Live Comedy Theatre located beneath The Charles Playhouse in Boston, hosting the Best in Live Stand-up, Improv, & Theatrical Comedy.

01/22/2026

This weekend is the LAST performance of The Naked Magicians before they set off on an epic North American tour.

After 4 months in Boston, you have one more chance to see the naughtiest and funniest magic show on planet earth. Only at Lil Chuck!

You can wear clothes, but they wont...

Get tickets at LilChuckBoston.com

12/03/2025

🎄Looking for a new holiday tradition in Boston? Improv Asylum presents ‘Twas, a laugh-out-loud, family-friendly comedy inspired by the classic poem “‘Twas the Night Before Christmas” playing throughout the holidays every Saturday and Sunday in Boston’s Theater District at Lil Chuck at The Charles Playhouse.

Get tickets at LilChuckBoston.com

11/26/2025

Our incredible 'Twas cast is ready for all you turkeys to join them at the Lil Chuck THIS WEEKEND! 🦃 ➡️🎄

Saturdays | 🕰️ 3:00 PM & 5:00 PM 🗓️ 11/29 - 12/27
Sundays | 🕰️ 3:00 PM 🗓️ 11/30 - 12/28

Tickets on sale now at LilChuckBoston.com!