Comedy Key West

Comedy Key West is an entertainment company that specializes in showcasing the best in live stand up comedy and original films in Key West, FL.

The Origin

In 2016, Joe Madaus, with his partner Anne Walters, started Comedy Key West in Anne's fitness studio. The show was called The Downward Dog Comedy Showcase. The first night had thirty nine audience members, fifteen comedians, and ran for a solid two and half hours. After a long, rousing, successful, event, Joe and Anne were promptly told to never come back. With a quick pivot, a week later, they found themselves in the beautiful BottleCap Lounge working with owners Carolyn Sullivan and Carmello Vitale. What started as a five-week experiment expanded into sold-out stand-up comedy shows nearly four nights a week.

During the Covid Crisis, the Club relocated to their current location, which is 218 Whitehead St. Unit 5, where comedy related events happen six nights a week.

Currently, Comedy Key West is the only comedy club in the Florida Keys. We host different headliners every week and serves as a spring board for local comedic talent to express themselves and practice their craft.

Our booker, Tom Dustin, brings many of the best acts in the world to the club to headline Thursday through Saturday.

On Monday, we offer a Paint N Chug with artist Lance Berry where even the most novice painter can leave with a masterpiece.

On Tuesday, we have a show-up and go-up open mic where new comedians and veteran headliners can test their latest material.