Tom Dustin hosts a show at Comedy Key West, a local business that opened in November 2000. Contributed

Comedy Key West just celebrated three years in business at 218 Whitehead St., a comedy club built from scratch by owners Joe Madaus and Tom Dustin and bar manager Kristen Borowski.

On Nov. 5, 2020, the group of locals opened up their own downtown club, having started out hosting shows at the Bottlecap in 2016. They quickly had sold-out shows and last weekend there was a waiting list to get in.

Dustin, a Boston-bred comic who toured the country for 12 years before landing in Key West, calls it a mom-and-pop shop. Dustin hosts almost every show and books the acts. But he also seats the audience and takes out the recycling.  

After the lights come back up, you’ll see a couple of local comics bussing the tables. Everyone pitches in, Key West local business style.

“I was a road comic sick of being on the road,” said Dustin, an Everett, Massachusetts native who books the acts. “I came down. Fell in love with the island.”

This weekend’s headliner is Ben Bailey, who hosted the smash hit game show “Cash Cab” for more than 550 episodes and won three Daytime Emmy Awards. He’s set to do a 6 p.m. and 8:30 p.m. show both Friday and Saturday plus an 8:30 p.m. show Sunday. 

Bailey, who has done a couple hundred comedy shows this year, has traveled the world over. But this is his very first trip to Key West. 

“[Dustin] just reached out to me months ago trying to figure out a way to get me to the club,” Bailey told Keys Weekly. “I’m psyched to come.”

“Cash Cab” quickly became a must-watch on Bravo but Bailey admits he didn’t see it coming.  

Ben Bailey, who hosted the hit Bravo show Cash Cab, is making his first trip to  the Keys to perform at Comedy Key West, Dec. 1-3, 2023.
Ben Bailey, who hosted the hit Bravo show Cash Cab, is making his first trip to the Keys to perform at Comedy Key West, Dec. 1-3, 2023. Contributed

“Everyone thought it was a dumb idea, myself included,” Bailey said. “People auditioned for the job and walked out.”

But early on, Bailey and the crew felt something click. 

“After three weeks of shooting we had a really good game,” he said. “And then at that moment we said, ‘Oh my God, this could actually be something. That game was really fun.’ The fact that it takes place in a moving cab is pretty unique.”

Comedy Key West was another success story that a lot of people didn’t see coming. 

When Comedy Key West began producing shows at the Bottlecap in 2016, Key West wasn’t known for comedy and plenty of people told Madaus the idea wouldn’t work. 

They started out with only a Thursday night show at the Bottlecap. Now, there are headliner shows four or five nights a week. Something’s on every day of the calendar, like the “Paint ‘n Chug” painting night on Mondays. 

This was a whole new ballgame: a homegrown business that gave a bunch of local comedians a chance while bringing the big names from across the country. 

Doug Stanhope, Joe List, Ari Shaffir, April Macie, Nick DiPaolo, Chad Daniels, Jamie Kennedy, Kevin Farley, Big Jay Oakerson and Nick Swardson are just a few top names that have appeared. 

The tipping point for success was simple, Dustin said: it’s locally owned and operated. 

“They didn’t have boots on the ground,” Dustin said of other clubs that couldn’t stick. “They were just sending comedians in. Joe was here and in the community. I saw the support from the locals. It was something new.”

But in 2020, the Bottlecap’s owners went into a different direction. The Comedy Key West team decided to go all in and rent their own space on Whitehead Street. 

“What makes us successful is support from our local community and the hard work of our team at Comedy Key West,” Madaus said. “If it wasn’t for Tom, Kristen, and everyone else, we wouldn’t have been nearly as successful, if at all, at our new location since leaving Bottlecap.”

Tom Dustin hosts a show at Comedy Key West. Contributed

Comedy Key West’s revolving door of heavy hitters started with Dustin’s pals from the Boston comedy scene. Then word spread of the little club in tropical Key West. The club’s name has recently come up several times in conversations on the Joe Rogan Experience.

“As they got bigger they told their other hugely successful friends that it was a cool place run by comics,” Dustin said. 

Key West gets comedy stars and the headliners get a taste of Key West living. Shaffir strolled into one show minutes before showtime, arriving by bicycle. Soon, he was onstage making the crowd roar. Most weigh in with punchlines about Key West’s defiant roosters and hard-drinking scene.

Comedian Lace Larrabee headlined shows in Key West last year and soon after won big on “America’s Got Talent.” 

[Note: Keys Weekly’s Gwen Filosa does comedy spots at Comedy Key West. She is getting funnier.]

For Dustin, who recently recorded a series of shows at the club for a new special, standup comedy is riding waves of emotions.

“It’s painful, embarrassing, exhilarating and awesome,” Dustin said. “I do it because I still love it. It’s different every single night.”

Steven Crane, a local comedian who appears onstage most nights, said Key West’s nightlife needed comedy.

“It’s been fantastic to have comedy in Key West,” Crane said. “I hate acoustic guitars with a passion. I love going to comedy and hearing different wits, insights and intrigues. Something that’s an alternative to listening to “Sweet Caroline” playing on acoustic guitar every 30 minutes.” 

Borowski, a longtime comedy fan, has been to the big clubs in cities like her hometown Chicago and had a great time. Comedy Key West packs the same punch, she said. 

“Ours is a great size,” Borowski said. “It’s more intimate. It’s kind of perfect.”

Gwen Filosa is The Keys Weekly’s Digital Editor, and has covered Key West news, culture and assorted oddities since she moved to the island in 2011. She was previously a reporter for the Miami Herald and WLRN public radio. Before moving to the Keys, Gwen was in New Orleans for a decade, covering criminal courts for The Times-Picayune. In 2006, the paper’s staff won the Pulitzer Prizes for breaking news and the Public Service Medal for their coverage of the Hurricane Katrina disaster. She remains a devout Saints fan. She has a side hustle as a standup comedian, and has been a regular at Comedy Key West since 2017. She is also an acclaimed dogsitter, professional Bingo caller and a dedicated Wilco fan.