Comedy Key West | Doug Benson Live

Doug Benson Live at Comedy Key West – Stand-Up Comedy Event

Comedy Key West welcomes legendary stand-up comedian Doug Benson for two exclusive nights of live comedy in the heart of downtown Key West. Known for his sharp wit, quick crowd interaction, and pop-culture fueled humor, Benson brings his nationally recognized comedy style to the southernmost comedy club in the country for a limited engagement.

Doug Benson has built a career spanning stand-up, film, television, and podcasting. He is widely recognized as the host of the hit podcasts Doug Loves Movies and Getting Doug With High, as well as the creator and star of cult-favorite films including Super High Me, The Greatest Movie Ever Rolled, and Chronic-Con: Episode 420. Television audiences know him from appearances on @midnight, The Trailer Park Boys, You’re the Worst, and as “Judge Doug” on Comedy Central’s The High Court. His live performances combine smart observational comedy with improvisation and audience engagement that make every show unique.

Performances take place at Comedy Key West, located at 218 Whitehead Street, an intimate venue that puts audiences just feet from the stage. Shows are scheduled for Friday, May 1, 2026 and Saturday, May 2, 2026, with two nightly showtimes at 7:00 PM and 9:00 PM. Seating is first come, first served, and early arrival is recommended for preferred seating.

Guests should note a two-item minimum applies during the show. Love Seats are available and are sold as one Love Seat equals two tickets. Due to adult themes and language, this event is restricted to ages 16 and older. To maintain the intimate comedy experience, audience members are asked to keep conversations to a minimum during performances.

Comedy Key West continues to be a premier destination for live stand-up comedy in Key West, hosting nationally touring comedians in a relaxed, high-energy setting that delivers memorable nights of laughter.

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