Cupid's Caloosa Comedy Nights with Headliner Rob Churchill

A question we often get at Caloosa Comedy is, "When is Rob Churchill going to headline?" We now have the answer. February 12-14, Rob Churchill is FINALLY headlining the club he started!!

Headliner Rob Churchill

Rob Churchill is a stand-up comedian who blends sharp observational humor with confident crowd work and a high-energy stage presence. Drawing from real life, relationships, and the absurdity of modern living, Rob’s comedy is honest, fast-paced, and relentlessly funny.

A favorite with live audiences, Rob knows how to read a room and elevate every show—whether he’s headlining, hosting, or featuring. His natural charisma and fearless approach keep crowds engaged and laughing from the first joke to the last. Rob Churchill is a comic who brings big laughs, strong connection, and a memorable performance every time he hits the stage.

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Host or Publisher Rob Churchill