Comedy Key West
218 Whitehead St. Unit 5
Key West FL 33040
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.
On a chilly October evening in 2007, Boston Headliner Tom Dustin and Joe Madaus were playing softball at Teddy Ebersol field in Boston, Massachusetts. Tom was the commissioner of the Boston Comedy Softball League and Joe sucked at pitching. Between innings, Tom made some very witty cracks about Joe's failure at throwing a softball and they both laughed. Tom laughed louder. Then Tom said, "Madaus, I'm not going to mess with you anymore."
Joe said, "Why not, Tom?"
Tom said "because you shouldn't kick a dog that doesn't bite." And they became instant friends.
Soon after, Joe moved to Key West to work on a TV show and Tom crushed his gigs across the continent and was the first American to win the Great Canadien Laugh-Off.
In 2016, Joe, with his partner Anne Walters, attempted a five week experiment and 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, sweaty, but successful show, Joe and Anne were promptly told to never do that type of thing again. With a quick pivot, a week later, they found themselves performing again in the beautiful BottleCap Lounge, thanks to Caroline Sullivan, who thought it be fun to have locals tell jokes once a week in her room. After a few shows, Joe realized the club was going to need some world-class talent to come to Key West if it was to make it past week five, so he called his old buddy Tom to see if he'd come down.
At first, Tom ignored the calls. "Who the hell is Joe Madaus?" Tom said, looking at his phone. "Is that the kid who couldn't pitch a strike in softball?"
After much convincing, Tom came down to Key West to be the first headliner in the fifth week and after his joke, the room vibrated off its foundation with the roar of laughter. The baby, named Comedy in Key West, was born. For three years, Tom sent some great acts while Joe hosted most of the shows. It was in 2019, that Tom took the plunge and moved to Key West full time.
During the Covid Crisis, the Bottlecap closed and Comedy Key West relocated to our current location, 218 Whitehead St. Unit 5, where comedy related events happen six to seven nights a week.
Comedy Key West is the only comedy club in the Florida Keys. We host different headliners every week and serve as a spring board for local comedic talent to express themselves and practice their craft.
Now, Tom brings many of the best acts in the world to the club to headline the club and Joe still sucks at pitching.
Check out our calendar for a complete list of events!