Filtering by: “Comedy”
Dave Williamson
Mar
4
to Mar 7

Dave Williamson

Named “Best Comedian in Miami” by the Miami New Times, Dave Williamson tours heavily, both headlining his own shows and as the supporting act for Bert Kreischer. His second album, “Trying My Hardest” was just released by Stand Up! Records and reached #1 in the iTunes Charts for Comedy. Dave's material is in heavy rotation on many SiriusXM stations. Dave often talks about family, highlighting stories from his youth to navigating the role of Father & husband himself. He is obsessed with BBQ, and hosts his own podcast called “Meat Dave”.

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Burgers & Buffett Tunes: A Tribute Show
Mar
5
to Mar 7

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Mar
6

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Cory Michaelis
Mar
11
to Mar 14

Cory Michaelis

Cory has a Dry Bar Comedy Special -"Bad Teacher" - that snagged over 80 million views. His debut album, "The Collage Dropout," was released by 800 Lb. Gorilla Records and charted at #2 on iTunes & Billboard (because it was the only album released that week). Cory was a finalist in the Seattle Comedy Competition which means he didn't win and was in Season 2 of Netflix's "Huge in France" with Gad Almelah.

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Burgers & Buffett Tunes: A Tribute Show
Mar
12
to Mar 14

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Mar
13

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Bad Teachers w/ Cory Michaelis and friends
Mar
15

Bad Teachers w/ Cory Michaelis and friends

Teachers (and former students) of Key West! Celebrate your long weekend with the comedy of a teacher who couldn't cut it - Cory Michaelis. After 12 years of teaching high school, Mr. Michaelis decided drunken hecklers were easier to deal with than students. Come see two class periods worth of mostly teacher/student material relatable to anyone who has ever been in a classroom. Non-teachers and teachers alike will love this show and some admin. will be on the show to keep us all in line. Irreverent (but PG-13-ish) comedy, shot specials, prizes, and a Kahoot!

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Sean Finnerty
Mar
18
to Mar 21

Sean Finnerty

From Longford, Ireland, Sean Finnerty decided to move stateside where a series of mature decisions that he failed to make led him to stand-up comedy. Recently he was rewarded for his efforts as he became the first ever Irish comedian to perform on the Tonight Show with Jimmy Fallon. Spending his first number of years in comedy based out of Orlando, Sean was selected for Comedy Central’s Up Next competition, made his television debut as co-host of Season 9 of Fireball Run on Amazon Prime. He has also performed at several festivals including Laugh Your Asheville Off, Edinburgh Fringe, and Electric Picnic, along with making it to the semi finals of the nationwide talent search Stand Up NBC. A keen eye for detail Sean has also developed a reputation as a Roaster and is currently the number 1 ranked roast comic in New York City.

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Burgers & Buffett Tunes: A Tribute Show
Mar
19
to Mar 21

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Mar
20

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Jimmy Dunn
Mar
25
to Mar 28

Jimmy Dunn

Jimmy Dunn is a stand-up comedian and actor from Boston, who currently plays “Moose” on the Paramount+ reboot of the iconic sitcom FRASIER. ​He can be heard most Tuesdays on The Greg And The Morning Buzz radio network. He got his start in "show business" telling jokes in a bar in Gloucester, Massachusetts, where he was paid in beer and fried clams. Since then, he’s gone on to perform at some of the world’s most prestigious comedy events, including the Late Show with David Letterman, CONAN, Montreal’s International Just For Laughs Comedy Festival, and Denis Leary’s Comic’s Come Home in Boston. Jimmy’s first major television role was as Sean McCarthy on the ​CBS sitcom, THE MCCARTHYS. He’s also written on several television projects, including two episodes of LOUDERMILK that he co-wrote with Academy Award winner Peter Farrelly.​

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Burgers & Buffett Tunes: A Tribute Show
Mar
26
to Mar 28

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Jessimae Peluso
Apr
1
to Apr 4

Jessimae Peluso

Jessimae Peluso is a stand-up comedian, writer, performer, TV and podcast host whose work blends raw comedy with emotional depth. Known for her breakout role on MTV’s Girl Code and hosting Netflix’s Tattoo Redo and Surviving Paradise, Jessimae has spent nearly two decades turning personal pain into punchlines.

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Burgers & Buffett Tunes: A Tribute Show
Apr
2
to Apr 4

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Steve Rannazzisi
Apr
8
to Apr 11

Steve Rannazzisi

For over 13 years, from the stage to the silver screen, Steve Rannazzisi has made audiences laugh. Currently, Rannazzisi stars and writes alongside Katie Aselton, Mark Duplass, Nick Kroll, Jonathan Lajoie, and Paul Scheer on the critically acclaimed FX Network comedy series, The League, which is produced by Jeff and Jackie Schaffer.

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Burgers & Buffett Tunes: A Tribute Show
Apr
9
to Apr 10

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Gastor Almonte
Apr
13
to Apr 14

Gastor Almonte

Gastor Almonte is a Dominican-American stand-up comedian, writer, and podcaster based in New York City. Raised in Brooklyn, he’s known for his warm, thoughtful delivery and deeply personal storytelling—blending culture and identity into comedy that’s both smart and emotionally grounded. Gastor has been featured on Comedy Central and NBC, and he performs regularly at top clubs and theaters across the country. His work has also appeared at major comedy festivals and across digital platforms, where he’s earned a reputation as a comedian’s comedian—respected for his writing, honesty, and point of view.

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Amos Gill
Apr
15
to Apr 18

Amos Gill

Amos Gill is one of Australia’s hottest comedians, now making waves internationally as a touring headliner across the USA, UK, and Australia. Known for his sharp humor and quick wit, Amos first gained attention as a beloved Adelaide radio host on Amos, Cat & Angus. After leaving radio in 2018, he quickly became a comic to watch, earning accolades such as runner-up in triple j’s RAW Comedy competition and hosting the Melbourne International Comedy Festival’s prestigious Comedy Zone.

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Burgers & Buffett Tunes: A Tribute Show
Apr
16
to Apr 18

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Tony V
Apr
22
to Apr 25

Tony V

In 1986 Tony V was named “Funniest Person in Massachusetts” by Showtime television. He followed this achievement with several performances on HBO, the Arts and Entertainment Network, Comedy Central and MTV. From 1987 through 1992 Tony V became the “spokesperson” for American Tourister Luggage. Remember the suit case smashing gorilla? It was Tony that gave the ape it’s distinct voice and temperament. Touring extensively in and out of his high tech forty-five thousand dollar yak hair gorilla suit, both Tony and his alter ego had many interesting adventures. If you get a chance ask Tony about a meeting between The Gorilla, Spuds MacKenzie and Ronald McDonald. You won’t believe your mind.

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Burgers & Buffett Tunes: A Tribute Show
Apr
23
to Apr 25

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
Apr
30
to May 2

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Eddie Gossling
May
6
to May 9

Eddie Gossling

From festivals to late-night television appearances, Eddie Gossling has been holding it down in the comedy industry for over 20 years. Known for his sharp wit and engaging stage presence, he has built a reputation and crafted a style that's equal parts edgy and endearing. Arguably his most notable accomplishment outside of stand up is his involvement with Comedy Central's "Tosh.0," where he served as a writer and co-executive producer for 12 seasons. Gossling's contributions to the show helped shape its comedic style and earned him recognition within the industry. In addition to his work behind the camera, Gossling has also made appearances on popular late-night shows like "Jimmy Kimmel Live" and starred in his own Comedy Central special.

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Burgers & Buffett Tunes: A Tribute Show
May
7
to May 9

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Sean Patton
May
11
to May 12

Sean Patton

Sean Patton is a comedian based in New York, by way of New Orleans. He began doing stand-up in the Crescent City and has since performed in comedy clubs and festivals across the world, including The Melbourne International Comedy Festival (2011, 2018), The Glasgow Comedy fest (2016), the Dublin Comedy fest (2017), and The Edinburgh Fringe (2017, 2019). Other festivals appearances include SXSW (2016, 2017, 2018, 2022), The Moontower comedy festival (2012, 2013, 2014, 2019), Just for Laughs Chicago (2013), Just for Laughs Toronto (2013) and Just for Laughs Montreal (2008, 2010, 2012, 2016, 2018).

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Burgers & Buffett Tunes: A Tribute Show
May
14
to May 16

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
May
21
to May 23

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
May
28
to May 30

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Feb
27

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Feb
26
to Feb 28

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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James Yon
Feb
25
to Feb 28

James Yon

This Florida native is one of America's hottest up and coming comedians. He can be seen each and every Sunday at 11pm hosting his own show, "Viral Breakdown" on the Afrotainment Channel on Dish Network. He has graced the stage with some of America’s top talent including, Joe Torry, Jimmy J.J Walker, Tom Rhodes and Michael Winslow. He was a finalist for NBC’s stand up for Diversity and appeared on the FOX comedy club. He was the 2011 and 2012 winner of the Orlando Improv’s “Clash of the Comics.” Now James spends his time touring clubs and casinos all over the country from Orlando to Las Vegas bringing the funny.

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Tom Dustin
Feb
24

Tom Dustin

Bostonian Tom Dustin is the funniest guy you’ve probably never heard of. He was the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off, (resulting in future contests being closed to American comics) 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. 


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Master Debaters
Feb
22

Master Debaters

Master Debaters is a live comedy debate show where stand-up comics argue ridiculous, relatable, and sometimes controversial topics—armed only with jokes, hot takes, and zero preparation. It’s fast, unpredictable, and fueled by crowd energy, with no topic off-limits and no debate ever taken seriously. Comics go head-to-head debating absurd topics in this high-energy live comedy show. Part stand-up, part roast, part chaos—Master Debaters delivers big laughs, bold opinions, and audience-driven moments every round.

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Caitlin Peluffo
Feb
20
to Feb 21

Caitlin Peluffo

Caitlin Peluffo has been featured on the Late Show with Stephen Colbert, The Late Late Show with James Corden, After Midnight, 2022’s Just For Laughs Festival, and has hosted her weekly podcast, Good Time Gal with Caitlin Peluffo for over three years. She has also been featured on Comedy Central’s “Featuring” series, and has a Don’t Tell Comedy Set with over 150k views on YouTube. With Caitlin, no subject is off limits, however, she did make a promise to her mother that she would never, ever discuss that one time she took those ‘whorish, yet tastefully executed’ photos for a guy she used to bang in the military. She may be a patriot, but a promise is a promise.

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Hemingway in a Funny Way
Feb
20

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Feb
19
to Feb 20

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Brothers From Another Mother Comedy Tour
Feb
15
to Feb 17

Brothers From Another Mother Comedy Tour

Jackie Flynn is a seasoned Boston-bred comedian and actor who has transitioned from legendary stand-up stages like The Comedy Store to a prolific screen career. Beyond his "Man Law" commercial fame, Jackie has appeared in The King of Queens and Veep. He currently stars as "Tony" in the Peter Farrelly-directed series Loudermilk.

Kevin Flynn has thrilled audiences for years with his stand-up comedy performances having headlined at clubs and colleges across the country. Flynn’s career as a comedian took off after winning the Boston Comedy Riot in 1988, where he then began appearing on numerous comedy specials. He has since added several film and television credits to his name appearing in The Heartbreak Kid with Ben Stiller; Me, Myself and Irene with Jim Carrey; Osmosis Jones with Billy Murray, and Sex and the City.

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Bad Monkey Comedy Night
Feb
14

Bad Monkey Comedy Night

Standup comedy showcase featuring cast members Brent Morin, Joey Avery, and Zavier Phillips from season 2 of the Apple TV hit series Bad Monkey. "Bad Monkey stars Vince Vaughn as a detective turned restaurant inspector in Key West who is pulled into a world of greed and corruption after a tourist finds a severed arm while fishing. And yes, there's a monkey."

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Hemingway in a Funny Way
Feb
13

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Feb
12
to Feb 14

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Mike Feeney
Feb
11
to Feb 14

Mike Feeney

Mike Feeney is a New York City-based comedian. His high energy and sharp wit captivate young and old audiences alike. He has been featured on The Tonight Show with Jimmy Fallon, NBC's Last Call with Carson Daly, Barstool Sports, Fox’s Laughs, Funny or Die, Sirius XM, The Chive, ABC's Right This Minute, Inside Edition, Reader's Digest and Food Network's Restaurant Stakeout.

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Dave Smith
Feb
7

Dave Smith

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.

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Fighting for Laughs, Too
Feb
7

Fighting for Laughs, Too

Join us for Fighting For Laughs, Too — a night of powerhouse comedy featuring Sam Norton, Preston Gitlin, and headliner “The Reverend” Bob Levy, hosted by local veteran and comedian Petey Rancel. Building on last year’s sold-out success, this event delivers big laughs for an important cause. 

 All proceeds benefit AHERO, a 501(c)(3) organization dedicated to preventing Veteran and First Responder suicide through fellowship, outdoor adventures, and community support.

 

Your $50 general admission ticket directly helps fund AHERO trips here in Key West — creating healing connections and life-changing experiences for our nation’s heroes. Come laugh, support, and make a difference!

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Burgers & Buffett Tunes: A Tribute Show
Feb
7

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Feb
6

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Hemingway in a Funny Way
Jan
30

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Jan
30
to Jan 31

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Jim Florentine
Jan
29
to Jan 31

Jim Florentine

For nearly 25 years Jim Florentine has been making audiences around the world laugh across nearly every type of media. Jim has recorded six stand-up comedy albums and shot four full-length specials. On television Jim hosted 7 seasons of VH1 Classic's "That Metal Show" as well as lending his voice to the ground breaking "Crank Yankers".

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Hemingway in a Funny Way
Jan
23

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Jan
22
to Jan 24

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Legion Comedy Club
Jan
17

Legion Comedy Club

Get ready for a night of world-class laughs as the Key West American Legion, in partnership with The Comedy Machine, presents a professional comedy extravaganza on Saturday, January 17. This one-night-only event brings a high-energy showcase to the island, featuring some of the most sought-after talent on the comedy circuit.

The evening’s headliners include Perry Sak, the winner of the prestigious $5,000 Mardi Gras Challenge, and Dr. Vien, whose clever observations have earned him a massive following on Dry Bar Comedy.

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Hemingway in a Funny Way
Jan
16

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Jan
15
to Jan 17

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Hemingway in a Funny Way
Jan
9

Hemingway in a Funny Way

Comedy Key West is happy to be bringing back 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 wine (Valpolicella) with your ticket.

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Burgers & Buffett Tunes: A Tribute Show
Jan
8
to Jan 10

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
Dec
30
to Jan 3

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
Dec
18
to Dec 19

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

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Burgers & Buffett Tunes: A Tribute Show
Dec
11
to Dec 13

Burgers & Buffett Tunes: A Tribute Show

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in-costume 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, Burgers & Buffett Tunes is a one-of-a-kind musical celebration of the 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.

View Event →