Comedy Key West

Friday, August 7th | 12:30pm

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

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.

Comedy Key West | A Pirate Looks Back: Jimmy Buffett Tribute Show 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-inclusiv...

This Week At Comedy Key West
Mark Chalifoux

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.

Tickets are available on our website at https://www.comedykeywest.com/events/139759

July 29 | 12:30pm
A Pirate Looks Back: Jimmy Buffett Tribute Show
https://www.comedykeywest.com/shows/374641

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.

Tickets:
https://www.comedykeywest.com/shows/374641

Comedy Key West | A Pirate Looks Back: Jimmy Buffett Tribute Show 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-inclusiv...

Another amazing night at the “Key West Game Show”! Family Feud, Jeopardy and the Newly Wed Game! A ton of laughs, games and prizes. Look for our next one on Monday, August 31st. Tickets available through our website! Andy Sands

This Week at Comedy Key West
Hemingway in a Funny Way
July 30th at 5:30 PM

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.

Tickets are available on our website at https://www.comedykeywest.com/shows/377823

Tonight through Saturday! (July 23rd-25th). Gabe Kea Gabe Kea joins us for the first time on our stage. Last night was 🔥🔥 Kea 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. He has been on the Bob and Tom Show multiple times and you can hear him played on Sirius XM Radio. We are thrilled to have him! Tickets available through our website.

Friday and Saturday night! Two shows left to catch Tom Dustin The only American to ever win The Great Canadian Laugh Off! (USA! USA! USA!) Winner of the Sam Adam’s Comedy Festival (Beer! Beer! Beer!) and is the subject of Joe List’s documentary, “Tom Dustin: Portrait of a Comedian”. If you haven’t seen his full headlining show, you’re missing out. Doors 7:00 Show 8:00. See you there!

Gabe Kea
July 22nd - 25th at 8 PM

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. Gabe has shared the spotlight as an opener for Joel McHale, Nikki Glaser, Bert Kreisher, Joey Diaz, Russell Peters, & Dave Chappelle.

He is a frequent guest on the nationally syndicated Bob & Tom Show. His debut album “Dumber Than a Fish” is available on iTunes, Spotify, Apple Music, & Amazon. Several tracks from that album can be heard on Raw Dog Comedy, Laugh USA, & Comedy Roundup via Sirius XM radio.

His interests include hockey, beer, and reinforcing Canadian stereotypes.

Tickets are available on our website at

Comedy Key West | Gabe Kea 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.