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The College of the Florida Keys
Comedy Key West
Fringe Theater Key West
Fury Catamaran
General Horseplay
HiNote, upstairs at General Horseplay
Hush Hush Theatre
Key West International Dance Company
Key West Woman's Club
Mac's Place
Marathon Community Cinema
Mary Ellen's Bar
Misfit Key West
Queer Keys Community Center
Tennessee Williams Theatre
The Social Club
Tropic Cinema
Truman Waterfront Park
William Weech American Legion Post #168
Williams Hall
Coast is Clear Music & Arts Festival
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Concerts & Music
Drag & Burlesque
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Family Friendly
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The College of the Florida Keys
Comedy Key West
Fringe Theater Key West
Fury Catamaran
General Horseplay
HiNote, upstairs at General Horseplay
Hush Hush Theatre
Key West International Dance Company
Key West Woman's Club
Mac's Place
Marathon Community Cinema
Mary Ellen's Bar
Misfit Key West
Queer Keys Community Center
Tennessee Williams Theatre
The Social Club
Tropic Cinema
Truman Waterfront Park
William Weech American Legion Post #168
Williams Hall
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Filtering by: “Stand up”
Brendan Eyre
Nov
4
to Nov 7
Comedy, Stand up

Brendan Eyre

  • Wed, Nov 4, 2026 8:00 PM Sat, Nov 7, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Brendan Eyre is one of the country's top club and corporate event comedians. His laid back, relatable style has proven a hit with audiences all over the world. He has appeared on Late Night with Seth Meyers on NBC, Comedy Central, Gotham Comedy Live, and his comedy has been viewed over 50 million times on TikTok. He was also a New Face of Comedy at the prestigious Just For Laughs comedy festival and he is heard regularly on Sirius XM radio.

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Nat Baimel
Nov
11
to Nov 14
Comedy, Stand up

Nat Baimel

  • Wed, Nov 11, 2026 8:00 PM Sat, Nov 14, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Nat Baimel is a comedian, upbeat problem solver, awkward philosopher, and optimistic nihilist with a knack for always looking on the bright side. His dark, smart, well-crafted material often tackles the most serious of subjects in a silly manner that will make you laugh as much as it will make you think.

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Greg Fitzsimmons
Nov
18
to Nov 21
Comedy, Stand up

Greg Fitzsimmons

  • Wed, Nov 18, 2026 8:00 PM Sat, Nov 21, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Greg Fitzsimmons 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.

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Colum Tyrrell
Nov
25
to Nov 28
Comedy, Stand up

Colum Tyrrell

  • Wed, Nov 25, 2026 8:00 PM Sat, Nov 28, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

After beginning his career in his home country of Ireland, Colum Tyrrell moved to New York City and quickly became one of the fastest-rising comics in the scene, performing regularly at the world-famous Comedy Cellar and many other top clubs. In 2023 he made his American national television debut on The Tonight Show with Jimmy Fallon and is now a touring headliner. Performing across the United States almost every weekend, he has earned a reputation as a ferocious standup act not to be missed.

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Tom Dustin
Oct
8
to Oct 10
Comedy, Stand up

Tom Dustin

  • Thu, Oct 8, 2026 8:00 PM Sat, Oct 10, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Landry
Sep
23
to Sep 27
Comedy, Stand up

Landry

  • Wed, Sep 23, 2026 8:00 PM Sun, Sep 27, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Aaron Berg
Sep
16
to Sep 19
Comedy, Stand up

Aaron Berg

  • Wed, Sep 16, 2026 8:00 PM Sat, Sep 19, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Tom Dustin
Sep
11
to Sep 12
Comedy, Stand up

Tom Dustin

  • Fri, Sep 11, 2026 8:00 PM Sat, Sep 12, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Key West's Best Showcase
Sep
10
Comedy, Stand up

Key West's Best Showcase

  • Thursday, September 10, 2026
  • 8:00 PM 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Come check out our best local comedians for one night only. 

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Dave Landau
Sep
3
to Sep 5
Comedy, Stand up

Dave Landau

  • Thu, Sep 3, 2026 8:00 PM Sat, Sep 5, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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The Key West Game Show
Aug
31
Comedy, Stand up

The Key West Game Show

  • Monday, August 31, 2026
  • 8:00 PM 10:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Key West Game Show!

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

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Jenny Zigrino
Aug
27
to Aug 29
Comedy, Stand up

Jenny Zigrino

  • Thu, Aug 27, 2026 8:00 PM Sat, Aug 29, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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. 

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Jeff Shaw
Aug
20
to Aug 22
Comedy, Stand up

Jeff Shaw

  • Thu, Aug 20, 2026 8:00 PM Sat, Aug 22, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Eeland Stribling
Aug
13
to Aug 15
Comedy, Stand up

Eeland Stribling

  • Thu, Aug 13, 2026 8:00 PM Sat, Aug 15, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Mark Chalifoux
Aug
5
to Aug 8
Comedy, Stand up

Mark Chalifoux

  • Wed, Aug 5, 2026 8:00 PM Sat, Aug 8, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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. 

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Hemingway in a Funny Way
Jul
30
Comedy, Stand up

Hemingway in a Funny Way

  • Thursday, July 30, 2026
  • 5:30 PM 7:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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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The Key West Game Show
Jul
27
Comedy, Stand up

The Key West Game Show

  • Monday, July 27, 2026
  • 8:00 PM 10:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Key West Game Show!

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

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Gabe Kea
Jul
22
to Jul 25
Comedy, Stand up

Gabe Kea

  • Wed, Jul 22, 2026 8:00 PM Sat, Jul 25, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Tom Dustin
Jul
16
to Jul 18
Comedy, Stand up

Tom Dustin

  • Thu, Jul 16, 2026 8:00 PM Sat, Jul 18, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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. 

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Myke Herlihy
Jul
9
Comedy, Stand up

Myke Herlihy

  • Thursday, July 9, 2026
  • 8:00 PM 10:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Ricky Cruz
Jul
1
to Jul 3
Comedy, Stand up

Ricky Cruz

  • Wed, Jul 1, 2026 8:00 PM Fri, Jul 3, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Patrick Garrity
Jun
25
to Jun 27
Comedy, Stand up

Patrick Garrity

  • Thu, Jun 25, 2026 8:30 PM Sat, Jun 27, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

After starting comedy at an early age, Patrick Garrity has developed into a veteran of the road. He doesn't just work the road he lives on it. Since 2010 he's been traveling the country nonstop on a never-ending tour with no actual residence. His versatility and raw talent make him one of the most unique stand ups touring today.

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Tom Arnold
Jun
18
to Jun 20
Comedy, Stand up

Tom Arnold

  • Thu, Jun 18, 2026 8:00 PM Sat, Jun 20, 2026 9:15 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.”

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Key West Comedy Competition
Jun
10
to Jun 13
Comedy, Stand up

Key West Comedy Competition

  • Wed, Jun 10, 2026 8:00 PM Sat, Jun 13, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Kyle Kinane & Matt Braunger
Jun
8
Comedy, Stand up

Kyle Kinane & Matt Braunger

  • Monday, June 8, 2026
  • 8:30 PM 10:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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. Matt Braunger is a comedian, actor, writer, etc. You’ve probably seen him in something, but you maybe don’t know what (Netflix’ Big Dumb Animal, Marvel’s Agent Carter, Mad TV).

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Billy Anderson
Jun
5
to Jun 6
Comedy, Stand up

Billy Anderson

  • Fri, Jun 5, 2026 8:30 PM Sat, Jun 6, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Billy Anderson is a standup comedian who can be heard on Audible’s “Sounds Like America” hosted by Jackie Kashian and seen on season 3 of the syndicated program “Laughs” on Fox television. In 2018 he released his first live comedy special titled “America’s Sweetheart” through The Harmon Brother’s Dry Bar Comedy series on Amazon Prime. You can see Billy both at the Hollywood Improv and touring internationally as the host of the hit comedy showcase The Gateway Show.

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Gateway Show with Billy Anderson
Jun
4
to Jun 7
Comedy, Stand up

Gateway Show with Billy Anderson

  • Thu, Jun 4, 2026 8:30 PM Sun, Jun 7, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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.

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Dan Soder
Jun
1
to Jun 2
Comedy, Stand up

Dan Soder

  • Mon, Jun 1, 2026 8:30 PM Tue, Jun 2, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Dan Soder is a New York City-based comedian who’s best known as ‘Mafee’ on the hit Showtime Billions series. His HBO Special “Son of a Gary” debuted December 7th, 2019. He has a Half Hour Special on Netflix’s “The Standups”. His first hour-long stand-up special, Not Special premiered in 2016 on Comedy Central.

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John Caparulo
May
28
to May 31
Comedy, Stand up

John Caparulo

  • Thu, May 28, 2026 8:30 PM Sun, May 31, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

A comedian known for his sharp wit, unique delivery, and brilliant affinity for cuss words, John Caparulo is a seasoned comic whose dry, no-nonsense Midwestern sensibility endears him to audience members of all kinds. He began his comedy career performing in clubs in Cleveland and Pittsburgh in the late ‘90s before coming to Hollywood to hone his skills on stage and work the door at the legendary Comedy Store. Caparulo's breakout performance at Montreal's Just for Laughs in 2003 led to spots on The Late Late Show with Craig Kilborn, The Tonight Show with Jay Leno, Jimmy Kimmel Live, and he appeared over 150 times as a panelist on Chelsea Handler’s popular E! show Chelsea Lately.

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An Evening of Storytelling & Comedy with Stormy Daniels
May
22
to May 23
Comedy, Stand up

An Evening of Storytelling & Comedy with Stormy Daniels

  • Fri, May 22, 2026 8:00 PM Sat, May 23, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

An evening of candid, comedic storytelling - followed by a live Q&A with the audience.

From life, to career, to scandal - it’s everything you want to know…and some things you may wish you didn’t. Whether you know her from television (SNL, VH1’s The Surreal Life, Host of OUTtv’s For the Love of DILFS), from magazines (Vogue, Vanity Fair, Rolling Stone), from the Peacock documentary Stormy, from movies (that can’t be mentioned here), or from the headlines - Stormy Daniels is now bringing her talents to the comedy stage. Stormy’s set is packed with hilarious stories from her time in adult entertainment, her personal life as a wife and mother… and of course, politics and scandal. Never one to shy away from the bold truth, every show ends with a live Q&A.

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Tom Dustin
May
20
to May 21
Comedy, Stand up

Tom Dustin

  • Wed, May 20, 2026 8:00 PM Thu, May 21, 2026 8:00 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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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Wyatt Cote
May
13
to May 16
Comedy, Stand up

Wyatt Cote

  • Wed, May 13, 2026 8:30 PM Sat, May 16, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

Wyatt Cote dropped out of college one year shy of graduation to pursue a career in comedy and has since become one of the top competitive comics in the country with five contest wins to his credit including the 2021 World Series of Comedy. He was the runner up in the 46th annual San Francisco Comedy Competition and now tours the country performing full time. His stand up has appeared on Laughs on Fox and ABC news.

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Sean Patton
May
11
to May 12
Comedy, Stand up

Sean Patton

  • Mon, May 11, 2026 8:30 PM Tue, May 12, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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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Eddie Gossling
May
6
to May 9
Comedy, Stand up

Eddie Gossling

  • Wed, May 6, 2026 8:30 PM Sat, May 9, 2026 8:30 PM
  • Comedy Key West (map)
  • Google Calendar ICS

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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