Cassandra Simpson has been performing as a stand-up comedian in Springfield for three years. For two of those years, she was the host for The Wakery’s open mic, but that gig came to an end when the venue closed its doors in August of 2025. The end of the downtown venue left aspiring local comics with even fewer options to test their material in front of a live audience in a town with already scarce resources in that area.
“I like to renovate my house and use power tools and get into trouble,” Simpson said, “and it just came to me: What if I make my own venue for comedy shows?” She decided to remodel a trailer into a one-of-a-kind mobile performance space to hitch onto the back of her car, creating opportunities for comedy, karaoke and other kinds of small-scale live shows anywhere she decides to park the rig. Think of it as a sort of food truck – but for comedy. She calls the project Rolling Laughs, and it made its public debut May 16 when she pulled up at the Enos Park Neighborhood Garden Open House and Resource Fair that Saturday morning.
“I’ve just been test-driving it around because I’m not familiar with pulling a trailer,” said Simpson, who was a finalist for best comedian in Illinois Times’ “Best of Springfield” in both 2024 and 2025. She is currently working with Lincoln Library, Downtown Springfield, Inc. and other organizations to arrange future events.
The Enos Park event is family-oriented, which means the Rolling Laughs mic was open primarily to children. “Anyone’s allowed to come and check it out but we were only going to let kids come up to the mic. And if they don’t know any jokes, my daughter, she’s 10, will be hosting with me.
I didn’t want to open it up to adults, because at open mics, you never know what the material is going to be like,” Simpson explained.
The original idea for Rolling Laughs was to work with local bars, restaurants and retail stores to help businesses bring in customers by hosting events. However, businesses have been slow to embrace the concept so far.
“It’s been veering off to more public, family-friendly organizations,” Simpson said. “I’m offering comedy or an open mic or karaoke. My original vision isn’t really happening quite yet.”
Upcoming appearances by Rolling Laughs include the “Rock & Rolling Variety Show” July 7 in Lincoln Park, a collaboration with Lincoln Library to launch its summer reading program. The show will include karaoke, lip syncing, jokes and more. Simpson also has a pop-up comedy show scheduled for July 17 at The Shed in Pawnee.
Follow Rolling Laughs on Instagram @rollinglaughsvenue and on Facebook at Rolling-Laughs for more details on future events.
Scott Faingold has been an instructor at University of Illinois Springfield, founding editor of Activator magazine, a staff reporter for Illinois Times and co-host of Old School Bleep, a music-centered podcast. He can be reached at scottfaingold@gmail.com.
This article appears in Summerguide 2026.
