Upcoming Events

A Must-See Lunchtime Tribute Show, live on stage in the heart of Key West!
[Reservations Recommended!]

There are many places to eat lunch in Key West. In some spots, you can have lunch with live music. But there’s only ONE place to have lunch with a legend. Join us for Key West’s only all-inclusive dine-in musical experience, revisiting the glory days of 1970s Key West when a young songwriter named Jimmy called this island home.

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in character as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.

Part lunch theater, part tribute concert, and part educational adventure, "A Pirate Looks Back" is a one-of-a-kind musical celebration of Jimmy’s songs, spirit, and the island where the legend began. This show is a MUST-SEE for all Buffett fans, music enthusiasts, or anyone looking for Key West’s most entertaining lunch experience.

Your ALL-INCLUSIVE ticket to this performance includes one cheeseburger with chips, one drink from the bar’s lunch menu, and tip. Additional beverages and drink specials will be available for purchase from the bar.

Please note:
There is a two item minimum for Show-Only attendees

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats. Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the day of the show.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you.

Thank you!

Comedy Key West Open Mic - Key West’s only open mic for comedy, music, variety and impropriety. Performers of all stripes welcome - comedians, musicians, poets, and those who don't know it. 

Signups are after 7 PM, Show Starts at 8 PM, 5 minute spots unless... (Click here for more)

Please join us in welcoming comedian Myke Herlihy to Comedy Key West!

Originally from Manchester, CT. Myke Herlihy is one of the most lovable jerks you’ll ever meet! After spending thirteen years behind bars, serving drinks not time, Myke now takes his bartender's wit to the stage. Whether he's discussing his failed relationships, ranting about the trials and tribulations of being an unwed father, or reminiscing over the insanity that was his childhood, Myke always manages to find the light at the end of the tunnel.

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats count as
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

With millions of followers across social media and a voice as loud as a Florida thunderstorm, viral content creator and comedian OMGITSWICKS IS taking the internet—and the Sunshine State—by storm. Known for his Florida-specific sketches, OMGITSWICKS has carved out a niche as the unofficial spokesperson for the hilarious chaos that is Florida life. 

With a loyal following on Facebook, TikTok, Instagram, and YouTube, OMGITSWICKS has become a must-watch creator for anyone who’s ever lived in, visited, or just heard about Florida. His videos resonate with viewers around the world, but Floridians especially see themselves in his comedic reflections of everything from hurricane prep and traffic meltdowns to backyard gator sightings and awkward small-town run-ins. 

With live performances now added to his growing repertoire, OMGITSWICKS is stepping off the screen and onto the stage, delivering the same high-octane energy and relatably ridiculous observations that built his brand online. OMGITSWICKS is more than a content creator—he’s a comedic force capturing the culture of Florida like no one else.

Also performing: Florida's Funniest Comedian of 2013 and Winner of Steve Harvey's National Talent Search KEN MILLER as well as Florida's Funniest Comedian of 2023 MYKE HERLIHY

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Edgy, original, and hilarious is the consensus of his comedy. Bostonian Tom Dustin is the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off. He was so hilarious that the contest was closed to all future American contestants (USA! USA! USA!) He was also the winner of the Sam Adams Comedy Festival (Beer! Beer! Beer!) He's done Comedy Central, The Comedy Channel (Canada), local & national radio, podcasts, festivals, and roasts. 

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats count as
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Please join us in welcoming comedian Gabe Kea to Comedy Key West. 

Comedian Gabe Kea's unbridled enthusiasm for entertaining audiences is what truly sets him apart. With a personality as big as his 6'5" frame, Gabe melds well-crafted jokes with his comedic physicality to create an unforgettable show.

Gabe spent his youth living in both the US and Canada and found his love for performing in St. Louis. Currently residing in Cincinnati, OH, Gabe can be found performing at comedy clubs throughout the country. He has been featured in the Limestone Comedy Festival in Bloomington IN, Gilda's Laugh Fest in Grand Rapids MI, and The Laughing Skull Comedy Festival in Atlanta GA.

Check out his Biography!

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats count as
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Key West Game Show! Interactive game show just like your on TV with FABULOUS PRIZES hosted weekly at Comedy Club Key West!

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Comedy Key West presents the first show paying tribute to the funny side of the life and works of Ernest Hemingway. A few blocks down the street from the famed Hemingway House, where he lived and wrote for nine years, and around the corner from his legendary watering hole Sloppy Joe’s, comedian James Scott Patterson takes us on an hourlong tour of Hemingway’s childhood, writing career, adventuring, and, of course, drinking days. The humor ranges from the tragic-comic (it is Ernest Hemingway after all) to the witty, wild, and difficult to believe. The show is a happy hour celebration from 5:30 to 6:30 including a complimentary glass of Hemingway’s favorite red or white wine (Valpolicella or Sancerre, “crackling cold”) with your ticket. Join us for a one of a kind look at one of Key West’s most enduring (and funny) figures. 

About the Host: James Scott Patterson is a standup comedian and writer who has performed on Comedy Central, been featured at the prestigious Montreal Comedy festival, and his latest album and comedy special “Superior Design” is available on all major streaming services. 

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 5:30 PM. Doors at 5:00 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Comedy Key West’s very own Tom Dustin and Kristen Borowski are getting married on this particular weekend, and the guest list includes the funniest people on the planet. 

So we decided to put on the greatest show we’ve ever done! This is an extremely unique event with an incredible lineup of comics. Limited tix will be sold to the general public for this show.

Comedians include: Joe List, Sarah Tollemache, Chad Daniels, Kelsey Cooke, Sam Tallent, Henry Phillips, Drew Dunn, April Macie, Dan Bulger, Landry, and more…

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Mark Chalifoux is a nationally touring stand-up comedian. He was most recently featured on Nate Bargatze's Nateland and has told jokes on Dry Bar Comedy and FOX. His comedy album, “Think Fast”, opened at #2 on Apple Music, has been streamed more than 5 million times on Pandora, and is played regularly on SiriusXM. His Dry Bar Comedy special has been seen millions of times across social media and he was the longtime writer behind The Dad, one of the most popular comedy accounts on social media. 

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats count as
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Eeland Stribling is your aunty’s favorite stand-up comedian.

Eeland is a regular at The Comedy Fort, Comedy Works and Denver Improv. He recently won the 2023 New Faces competition at Comedy Works! He also regularly tours in Boston, Chicago, LA, Austin and venues across the country. He has traveled across the world teaching about fly fishing and telling jokes everywhere he can.

He has performed at High Plains Comedy Festival, Limestone Comedy Festival, 10k Laughs, and many more festivals.

Please note:
There is a two item minimum.

Groups who purchased tickets together will be sat together, but seating is first come, first serve. Please arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats count as
If you are purchasing Love Seats: 1 Love Seat counts as 2 tickets.
Please do not purchase two Love Seats, if you are only coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!

Please join us in welcoming Dave Landau back to Comedy Key West. 

Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening,” and he is a regular panelist on Fox shows such as “Fox Across America,” “Who Can Forget?,” and “Kennedy.” He was also a finalist on season 8 of “Last Comic Standing” on NBC.

Check out his Biography!

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

During the Show

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

Thank you!