Bill Squire returns with his boldest hour yet in Lil’ Stinker, a comedy special that proves no topic is too messy, awkward, or outrageous to laugh about. Filmed live at The Brothers Lounge in his hometown of Cleveland, Squire leans into his reputation for being both “too woke” and “too offensive”—a contradiction he wears proudly. With sharp storytelling and unfiltered honesty, he dives into the contradictions of modern life, the absurdity of human behavior, and the strange comfort of finding humor in places we usually avoid.
Equal parts biting and self-aware, Lil’ Stinker is a fearless set from a comic who thrives on walking the tightrope between provocation and relatability. For anyone who enjoys stand-up that’s unapologetic, unpredictable, and just a little mischievous, Bill Squire’s Lil’ Stinker is not to be missed.
Bill Squire: Bill Squire is an American stand-up comedian, writer, and radio personality based in Cleveland, Ohio. He’s best known as a co-host of The Alan Cox Show on WMMS, a popular afternoon radio program where he brings sharp humor, quick wit, and offbeat perspectives.
On stage, Squire’s comedy blends personal stories, absurd observations, and unapologetically honest takes on relationships, family life, religion, and everyday struggles. His style mixes storytelling with a dry, slightly self-deprecating delivery, making him relatable and consistently funny.
Squire has released several comedy albums and specials, including “Just Say Your Jokes,” “Decaf Please,” and most recently “Lil’ Stinker” (2023), which showcases his evolution as both a writer and performer.
He’s also known for his sketch work, YouTube sketches, and contributions to the Cleveland comedy scene, where he’s considered a staple performer.
