Comedy Key West

Comedy Key West: Premier Key West Comedy Club & Live Stand-Up Showcase

Comedy Key West is an acclaimed entertainment establishment specializing in live stand-up comedy and original films in Key West, FL. Its origin traces back to a chilly October evening in 2007, when Boston headliner Tom Dustin and Joe Madaus shared a humorous moment during a softball game in Massachusetts. A witty remark by Tom—“because you shouldn't kick a dog that doesn't bite”—sparked an instant friendship that eventually led to transformative comedy collaborations.

After Joe relocated to Key West to work on television, Tom’s nationwide success—including winning the Great Canadien Laugh-Off—set the stage for an innovative venture. In 2016, Joe, alongside partner Anne Walters, launched a five-week experiment in a local fitness studio with “The Downward Dog Comedy Showcase.” A rapid pivot to the BottleCap Lounge, courtesy of Caroline Sullivan, led to a series of successful performances. Recognizing the need for world-class talent to elevate the local scene, Tom was invited as the first headliner, igniting the birth of Comedy Key West. By 2019, Tom had made Key West his home base, further cementing the club’s reputation.

During the Covid crisis, when the BottleCap closed, the venue relocated to 218 Whitehead St. Unit 5, Key West FL 33040, where comedy events now take place six to seven nights a week. As the only comedy club in the Florida Keys, Comedy Key West hosts a dynamic lineup of headliners and serves as a launching pad for emerging local comedic talent. The current event schedule features celebrated performers such as Mary Mack on March 01, Kurt Metzger from March 02 to March 04, Dwayne Perkins from March 05 to March 08, and more exciting shows including Hemingway in a Funny Way (March 07 – April 25), Chad Daniels (March 09 – March 11), John Caparulo (March 13 – March 16), The Music Comedy Jam! on March 17, Comedy Key West Open Mic (March 18 – March 25), Tom Dustin (March 19 – March 23), Patrick Garrity (March 26 – March 29), Andy Hendrickson (April 02 – April 05), Jim Norton: Now You Know Tour (April 18 – April 19), and Ed Larson (May 09 – May 11). For more details or reservations, contact (305) 985-7370.