John Caparulo at Comedy Key West

John Caparulo Live at Comedy Key West

Comedy Key West welcomes nationally recognized stand-up comedian John Caparulo for a multi-night run bringing his razor-sharp humor to the southernmost comedy club in the country. Performances take place Thursday, May 28 through Sunday, May 31, 2026, with shows beginning nightly at 8:30 PM at 218 Whitehead Street, Unit 5, Key West, Florida.

Known for his unmistakable Midwestern delivery, fearless honesty, and expertly timed punchlines, John Caparulo has built a loyal following through decades of club, television, and festival appearances. His career launched in the late 1990s in Cleveland and Pittsburgh before gaining national attention after a breakout performance at Just for Laughs Montreal. That momentum led to appearances on The Tonight Show with Jay Leno, Jimmy Kimmel Live, The Late Late Show, and more than 150 episodes as a panelist on Chelsea Lately.

Comedy Key West offers an intimate setting where Caparulo’s dry, no-nonsense comedic style thrives. Seating is first come, first served, and early arrival is encouraged for preferred seating. A two-item minimum applies during all shows. Guests attending as part of a group are encouraged to coordinate seating arrangements in advance.

Due to mature themes and language, all performances are ages 16 and up. Audience members are asked to keep conversations to a minimum during the show to maintain the best possible experience for performers and guests alike.

This limited engagement is an ideal opportunity to catch one of stand-up comedy’s most recognizable voices live in Key West.

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