Upcoming Events

The Gateway Show has a simple premise: Stand-up comedians take to the stage sober to tell their BEST jokes, then they go to an undisclosed location to get WAY too high, only to come back to the stage and ATTEMPT to tell more jokes while completely stoned.

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 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 and one drink from the bar’s lunch menu. 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!

Kyle Kinane is a comedian from Addison, Illinois. According to Wikipedia, he is a notable person from that town. Other notable residents of Addison have been the boxer Leon Spinks and a woman who wrote poetry about Beanie Babies. Raised in such a cultural fondue pot as this, it was natural for Kyle to find his way from warehouse work into show business. As a comedian, he has been seen on Conan, The Tonight Show, Netflix’s “The Standups,” and three of his own hour-length specials on Comedy Central. As an actor, he’s been in the Judd Apatow series “Love” and truTV’s “Those Who Can’t.”

Matt Braunger is a comedian, actor, writer, etc, and this is his website. You’ve probably seen him in something, but you maybe don’t know what (Netflix’ Big Dumb Animal, Marvel’s Agent Carter, Mad TV). Here you can see where he’ll be on tour, stream or buy his specials and albums, listen to his acclaimed podcast “Advice from a Dipshit with Matt Braunger,” and follow him on his various socials.

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!

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)

Comedy is art. And art is subject to opinion. Which makes it impossible to judge fairly. But we’re doing it anyway…

Florida comics bring their best bits to our stage, and the audience helps pick who should win the night and the cash! 

Wednesday’s show will also feature an interactive first look at “The Key West Gameshow”, a fantastically fun night with your favorite game shows, coming soon to Comedy 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.

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!

Tom Arnold is an actor, writer, and comedian with a career spanning over forty years, appearing in hundreds of hours of television and over one hundred and fifty films. He is best known for roles on Roseanne, True Lies, Nine Months, The Stupids, Carpool, McHale’s Navy, Big Bully, Austin Powers, and Soul Plane. He has hosted Saturday Night Live four times, has had three HBO specials, and starred in four sitcoms. Tom has won a Golden Globe, a Humanitas Award, and a Peabody Award, and has appeared on the Jimmy Kimmel Show, Howard Stern, and was a co-host on “The Best Damn Sports Show Period.”

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!

The Never Ending tour never stops for Patrick Garrity!  For over 20 years, Garrity  has toured the country growing his audience of followers who can’t get enough of his smart and witty take on current events, life’s hardships and the obvious, and not-so-obvious, ironies of our society. Sometimes solo, sometimes with fellow comics from his entourage of talented funny friends; The Never Ending Tour is always full of comedy entertainment that audiences love to see over and over again.

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!

With a comedy career spanning over 20 years Ricky Cruz is a nationally seasoned talent. Working alongside the greats of comedy, touring with the late Ralphie May, and appearing on comedy specials for HBO, NBC, and Sirius Xm radio. He’s all grown up and sharing the twisted true-life tales that have shaped him and his point of view along the way.

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!

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!

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!