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!

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!

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)

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 Jeff Shaw back to Comedy Key West. 

Jeff Shaw is an accomplished stand-up comedian and published writer whose two Dry Bar Comedy specials have garnered over 10 million online views and have streamed on both Peacock and Roku. Jeff has also competed on “America’s Got Talent,” is a regular on SiriusXM Radio, has been a guest on the nationally syndicated “The Bob & Tom Show” radio program, and has appeared on “Comics Unleashed with Byron Allen” on CBS.

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 the sweetness of the midwest and the sharp edge of the east coast, Jenny Zigrino brings a powerful comedic performance to any stage. She combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty and undeniable charm create a compelling comedic experience you won’t forget. 

She made her late night debut on Conan with Conan O’Brien and performed a total of three guest appearances. In 2023 she performed on The Late Late Show with James Corden and was met with rave reviews. She was a Just For Laugh’s New Faces in 2016 and since then has been featured on Comedy Central, MTV, HBO, Netflix is a Joke and many others. She starred in films such as Bad Santa 2 along Billy Bob Thornton and in the horror comedy Too Late in 2021. She’s headlined festivals like Moon Tower, New York Comedy Festival, and High Plains Comedy Festival. She’s written and performed several comedy specials including Comedy Central Presents the Half Hours and her latest hour special Jen-Z premiered on Comedy Central Digital in 2023. Her latest appearance on After Midnight with Taylor Tomlinson has been hailed as one of the funniest episodes yet by fans. Her most recent Don’t Tell Comedy special is out now.

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.

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!

Aaron Berg is a fixture on the NYC comedy scene, he is undeniably hilarious and packs the maximum amount of laughs per minute possible. No two sets are ever the same. Aaron was just cast in Uwe Boll’s new feature film The First Shift, which bolsters his acting resume to well over 50 projects including cult classic feature films like The Boondock Saints 2, Detroit Rock City, The Kitchen opposite Melissa McCarthy and Saturday Night Live’s The Ladies Man.

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!

Landry is best recognized for his likable hair, sprouting from charismatic follicles. He is a Canadian born interracial love child whose hybrid existence when mixed with a little dysfunction, makes for a fantastic recipe of comedy goulash. He is the winner of both the Boston Comedy Festival and the World Series of Comedy but none of that matters so long as his mom thinks he's funny. With a smile that lights up a room and a personality to match, there is no telling what great things this young performer will achieve.

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!

Greg is an accomplished stand-up, a four-time Emmy-winning writer, and a host on TV, radio and his own podcasts. Host of the popular FitzDog Radio podcast, as well as the Sunday Papers and the Childish podcasts, Greg has made more than 20 visits to The Joe Rogan Experience and 50 visits to The Howard Stern Show, and one hundred on The Adam Carolla Show. Howard gave Greg his own show on SiriusXM, which ran for more than ten years. He’s done dozens of appearances on all the late-night talk shows including Letterman, The Tonight Show, Conan O’Brien and Jimmy Kimmel.

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!

Dana Gould started performing stand-up comedy at the age of 17, three short weeks out of high school. Dana Gould has performed in several HBO specials, as well numerous guest appearances on "Late Night With Conan O'Brien" and "The Late Show with David Letterman". Gould recorded the CD Funhouse, which was called "a comedy CD" by Billboard magazine. As an actor, he appeared on "Seinfeld" and "The Ben Stiller Show". After writing the pilot "World On A String" (with Jay Kogen), Gould co-created MTV's late, lamented, Super Adventure Team (with Rob Cohen). Dana Gould then joined the staff of "The Simpsons", where he squatted for seven years. Stand up remains a big part of his career, and he continues to perform regularly.

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!

Luis J. Gomez is a New York-based comedian and podcast host known for his bold, unapologetic humor. He’s the co-host of the wildly popular Legion of Skanks podcast, where he and his fellow comedians dive into unfiltered, often controversial conversations. Luis also hosts The Regz, and Story Warz where he brings his dynamic energy, sharp wit, and comedic flair to a range of topics. With a loyal fanbase and a strong presence in both comedy and podcasting, a night with Luis J Gomez is always a great time.

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!

Legendary Boston Comedian Lenny Clarke is back on the road with his “No holds barred” stand up comedy tour! Lenny was featured in the Dennis Leary FX show RESCUE ME and has also been in some great comedy movies; There’s Something about Mary, Fever Pitch, Stuck on You and Me, Myself and Irene to name just a few!

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!

A hybrid of Minnesota and Wisconsin (with a severe cheese dependency), comedian Mary Mack is a favorite on radio shows and podcasts around the country including, Marc Maron's WTF Podcast, The Bob and Tom Show, and The Grand Ole Opry. Mary stars as Jesse in the Hulu cartoon Solar Opposites by the creators of Rick and Morty. She’s appeared in Montreal’s Just For Laughs Festival, HBO’s Andy Kaufman Awards, San Francisco’s Sketchfest, and the Dry Bar comedy series.

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 a smooth and clever style, a great smile and a contagious laugh Kevin has been entertaining in clubs and colleges across the country.  In 2000 he was the winner of the Midwest region of the HBO “Comedy Competition” and flew to Los Angeles to compete as a finalist.  He performed on Comedy Central’s “Premium Blend” in 2003, and finished 2nd in the Boston Comedy Competition in 2005.  He was a semi-finalist on NBC’s “Last Comic Standing” in 2015.  Kevin has appeared on Comedy Central, NBC, CBS and Fox.  His Dry Bar Comedy Special, “Clean & Unfiltered” has over  7 million views.

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!

Dave Smith is a comedian, political commentator, radio and tv personality. Dave is a regular guest on The Joe Rogan Experience, Tim Pool, Kennedy, and The Greg Gutfeld show. In 2017 Dave’s debut comedy special ‘Libertas’ was released and spent over three weeks at #1 on the ITunes comedy chart. Dave is the host of ‘Part of the Problem’ a libertarian podcast about current events and the evils of government and the corporate media as well as his comedy podcast Legion of Skanks.

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!