Upcoming Events

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". On radio Jim has been a regular on The Howard Stern show, the Opie & Anthony show and currently hosts his own program on Sirius XM. In addition Jim is a best selling author, world-renowned voice over talent and has been featured in the film's "Beer League" with Artie Lange and "Trainwreck" with Amy Schumer.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Jim Florentine!

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Comedy Key West presents The MadHouse - 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. Show starts at 8:30 PM.

Let us know if you're interested in performing by emailing us at comedykeywest@gmail.com.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Wyatt Cote who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Hosted by Caleb Hogan, Comedy Key West presents the Key West Music Comedy Jam!

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Kevin Farley is an entertainer to the core. Over the past 3 decades he has made audiences laugh, cry, smile and think as a stand-up comedian, actor, filmmaker and podcaster.

Kevin, who currently tours around the world performing his brand of "positive" stand-up comedy, got his start studying at the famous Second City in Chicago. Soon after he starred in films such as Black Sheep (with his brother Chris) and The Waterboy (with Adam Sandler), and leading roles in An American Carol and White Knight. He has also made guest appearances on Curb Your Enthusiasm, Rules of Engagement, Just Shoot Me and Comedy Central's Drunk History to name a few. 

Kevin has hosted many live shows and events and has been featured Nationally on The Today Show, The View, Extra, Good Morning America and radio shows from coast to coast.

You can currently find Kevin lending his voice to "F is for Family" on Netflix, on his podcast "Kevin Farley on the Road" and performing stand-up comedy at the best comedy venues and theaters nationwide.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Kevin Farley, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Mike Cannon is a New York City based comedian, podcaster and actor. 2023 has already been a big year for Mike. In February he sold out Gramercy Theatre in his hometown of NYC and continues to headline internationally in some of the most iconic venues throughout the world. Mike is also a contributing producer, writer and panelist for ViceTV's Super Maximum Retro Show hosted by Chris Distefano. In 2022, Mike released two Independently produced comedy specials - WHITE PRIVILEGE HOMELESS - and a crowd work (on edibles) special - MIKE CANNON'S HUGE MISTAKE - on Youtube where they have each received thousands of positive reviews from fans, comedians and critics alike. His debut comedy special – LIFE BEGINS – was released in January 2020 on YouTube and earned a spot on Laugh Button’s Top 35 Comedy Specials of 2020. The album – LIFE BEGINS – was released February 2020 through 800 Pound Gorilla Records. It was recognized as one of Interrobang’s Top 11 Albums of 2020 as well as one of Sirius/XM Raw Dog Radio’s Top 10 Comedy Albums of 2020. Recently, Mike earned critical acclaim for his acting as the lead role in the feature film Timing on Amazon Prime. Mike’s first comedy album – I Think It Just Kicked In – debuted at #1 on the iTunes comedy charts and #7 on Billboard comedy charts and has over 5 million streams on Pandora.

Mike appeared as a guest on the popular Barstool Sports series Friday Night Pints and Answer The Internet, a guest on Comedy Central’s Stupid Questions with Chris Distefano, an actor on Blake Griffin’s Double Cross on TruTV, a panelist on Comedy Central’s The Nightly Show with Larry Wilmore, a talking head on TruTV’s Greatest Ever, a sketch performer on TruTV’s Top Funniest, a comedian panelist on MTV’s Failosophy and Money From Strangers, a regular guest on Fox’s Red Eye, a talking head on MSG’s The Bracket, and was a contributing writer and performer for MTV2’s Guy Code. He is a regular guest on several Sirius/XM Radio shows including The Jim Norton and Sam Roberts Show, KFC Radio, Barstool Radio, and Barstool Breakfast, The Bonfire with Big Jay Oakerson and Dan Soder and Bennington.

Mike is co-host of Here’s the Scenario podcast and host of two digital series - Heads Up with Mike Cannon and Mike Takes Edibles. Mike has been a guest on several popular podcasts including Andrew Schulz’s: Flagrant 2, Girls Gotta Eat, Chrissy Chaos, KFC Radio, Are You Garbage?, Robert Kelly’s You Know What Dude!, Stuff Island, Doug Benson’s Getting Doug with High, Ari Shaffir’s Skeptic Tank, Jim Norton’s The Chip Chipperson Podcast, Joe List’s Mindful Metal Jacket and Jessica Kirson’s Disgusting Hawk. He’s also been a guest on Dad Meat, History Hyenas, OOPS The Podcast, Legion of Skanks, The Dad, Calta and Kelly, Comedy Cellar Nightly, and Opie Radio.

In March 2017, Mike performed stand up on AXS Gotham Comedy Live with host and comedy icon (and first time stand-up performer) Fran Drescher. He was a finalist in the 2016 and 2014 New York Comedy Festival’s “NY’s Funniest” contest. Previously, Mike hosted the long-running Irish Goodbye Podcast and the popular weekly web-series The Weed News with Mike Cannon. He was a co-host of Cosmopolitan Magazine’s series Sexy vs Skanky and a featured performer on VH1’s Why Am I Still Single?

Mike is always developing new material. He regularly tours the country, and, when home, he plays all the major New York City clubs including the Comedy Cellar and New York Comedy Club. It makes no difference to him whether he’s performing in a club, a bar, a casino, an elevator (done that twice), a parking lot, a rooftop, on a fake beach in front of a freight train, or in technically-legal underground speakeasies, comedy is his life. Mike is dedicated to making the majority of you laugh and the rest of you confused, yet oddly satiated.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Mike Cannon who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Originally hailing from San Francisco, CA, Caitlin Peluffo is a comedian currently living in Brooklyn, NY. After a brief six year stint in art school where she studied performative video art (no, really…that’s a thing) she has expanded her talents to the stage. Peluffo has opened for comedians like Maria Bamford, Gilbert Gottfried, Gary Gulman, Colin Quinn, and the late Kevin Meany. She’s been featured everywhere from New York Comedy Club in the Big Apple to clubs nationwide talking about how she came to be such a lovable loose cannon.

She co-produces a monthly comedy show in Brooklyn with Emily Winter at Precious Metal Bar called Karen. She also recently participated in The Breakout Artist Series for Carolines on Broadway. 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.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Caitlin Peluffo who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Carmen Lynch has a multitude of late night TV appearances including The Tonight Show Starring Jimmy Fallon, The Late Show with Stephen Colbert, The Late Show with David Letterman, Conan and The Late Late Show with Craig Ferguson. Carmen has also appeared on Inside Amy Schumer, That Damn Michael Che, Life & Beth and the documentary Hysterical (produced by Jessica Kirson.) Carmen also has two new comedy specials: one in English titled Queef Week and one in Spanish called Carmen Lynch en Español (both streaming on YouTube.) You can find her on all social media @carmencomedian.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Carmen Lynch who will be performing with John Reynolds.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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.

Following his performance at The Montreal Just for Laughs Comedy Festival, Gossling voiced the character Scraw the Vulture in Disney's animated feature film "The Wild.”

Growing up in a military family that moved around frequently was paramount to Eddie’s ability to connect with audiences and find humor in a wide range of topics, making him a favorite among comedy clubs and fellow comedians alike.

When not touring, you can hear Eddie on the “Tosh Show” podcast, which he helps to produce in Los Angeles.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Eddie Gossling, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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. 

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 5:30 PM. Doors at 5:00 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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. He most recently released a new special for DryBar Comedy.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Landry, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

"Let me tell you something, friends. Doug Stanhope is one funny sumbitch. He's also one of the most twisted individuals I've ever met, but that's part of his charm. He's one of those comics that doesn't make shit up. He lives a mad, mad life and what he remembers he reports back to us. He's been known to bare his soul, and other things, right there on thestage. If you're easily offended, stay home this week. Watch Matlock or something. But if you like your comedy rough, raw, and rowdy, there's no one better than Doug Stanhope. Have I made myself clear?"
- Austin Chronicle

"He blazed with the honesty, outrage and lucidity that made his name... Much of what's wrong with the world melts away in Stanhope's flame... comedy with brains and guts and a heart", "the charm, don't-give-a-damn swagger and aggressive intelligence that make for important, exciting comedy." 
- The Guardian, London 

"There's a kind of Olympic torch of extreme American comedy, which passed from Lenny Bruce, through Richard Pryor and Sam Kinison... to the late Bill Hicks. Stanhope is the latest, and equally brilliant, bearer." 
- Independent on Sunday

"Stanhope's stage show is a momentous thing to behold. Don't expect typical Bush-bashing or paper-thin material - he takes no prisoners in his ruthless baiting of everything that gets under his skin." Glasgow Evening Times "On his way to self-immolation, Stanhope works through an hour of brilliant material which slaughters just about every sacred cow on the farm." 
- The Scotsman, Edinburgh

"Stanhope breaks down the walls of decency. He uses profanity, but nothing he says is meant to shock. Everything he says is designed to make the audience laugh. Stanhope has worked his way to become one of the best comics around." 
- The Reno Gazette Journal

"Ask anyone whose opinion matters, and they'll tell you Doug Stanhope is one of the top ten stand-ups in the world today. Stanhope's confrontational stance comes from the rough, blistered underbelly of America's trailer parks; he's a feral, aggressive man full fuelled by primal urges to drink, fight and screw ­ and the corrosive material has all the venomous aggression you might expect from that background. But what underlines it, and makes it so untouchably good, is the passion and conviction with which he holds his intelligent beliefs, informed by sensibilities that might seem alien to such a no-nonsense, pig-headed persona." 
- Chortle UK

"Watching Stanhope is half entertainment and half survival. It's that perfect mix of substance and chaos that made punk rock fun in the seventies. There's a very real chance a fight will break out or all hell will break loose and the tension is intoxicating." 
- ClevelandYucks.com

"If there's such a thing as being too honest in comedy, Doug Stanhope may come close. Known for brutal honesty, railing against the "system" and caring very little about what his audience thinks, Stanhope has elevated himself to become one of today's most talked-about artists." 
- TimeOut, Chicago

"Doug Stanhope is a gritty comic that mixes atrociously profane gutter humor with acerbic social commentary that would likely get him killed if he weren't so damned funny. If there any one thing about Stanhope that's telling of his talent, it's that his material bears repeated listening. Unlike so many of his contemporaries and influences, you can listen to the same Stanhope CD over and over and always get something new out of it." 
- Deadtide.com

"Stanhope possesses a range of stunningly effective stand-up skills and a talent for subtle verbal phrasing. More importantly, he speaks out not only about sex and drugs and so-called perversions, but also about social and political hypocrisy. And his rants command attention because he clearly means every single thing he says." 
- TimeOut, London 

"Some of the sharpest and most biting cultural commentary you'll see in a comedy club." 
- St Louis Post-Dispatch

"See him very soon, because he describes his own intake of drink and drugs as staggering. "Jesus died for your sins," he reminds us. "I'm doing it for your mere entertainment." Well, he isn't Jesus. But at his peak only a literal miracle could produce better, more challenging comedy."
- EdinburghGuide.com

"Sharp, off color, and howlingly funny" - The San Francisco Chronicle

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Doug Stanhope, with feature act Andy Andrist.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Matt Bergman realized his love for comedy in his last year of college where he was pursuing a degree in criminal justice. After graduating he realized he was afraid of criminals and decided stand-up comedy was the way to go.

It was a wise move. Bergman is easily relatable and versatile, a skillset that has opened the door to TV appearances on Gotham Comedy Live, Comedy Central Live, and a Dry Bar Comedy Special.

His recent album “Mostly Nice” was called “really tough to purchase” by his mother who still doesn’t understand how iTunes or streaming works. It was released on Rhizome Records and can be heard on Sirius/XM. It’ll be released as a special in December of 2024

Contact Matt for more info or follow him on Instagram for comedy videos and photos of his dog, Wilma.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Matt Bergman, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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.

Dave Smith is a comedian, political commentator, a TV and radio 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 co-hosts the Legion of Skanks podcast and hosts ‘Part of the Problem’ a libertarian podcast about current events and the evils of government and the corporate media.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Dave Smith with feature act, Robbie "The Fire" Bernstein.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Jackie Flynn

Jackie Flynn is an actor and comedian with prominent standup appearances, as well as extensive film credits to his name. Jackie has emerged as one of the funniest and most talked about comedians to come out of Boston, joining the ranks of Steven Wright, Denis Leary, Lenny Clarke, and Jay Leno, and gracing the stages of the IMPROV, COMEDY STORE, FLAPPERS, LAUGH FACTORY, and other noteworthy venues. He has parlayed his success as a stand-up to firmly establish himself in the film and television arena, featuring in several episodes of the hit series “The King of Queens,” and recent guest appearances on “Veep” on HBO and the Disney Channel’s “Bizaardvark.” He is also recognized for his role alongside the likes of Burt Reynolds, NFL Coach Jimmy Johnson, and Jerome Bettis as one of the "Men Of The Square Table" in the hugely popular Miller Lite "Man Law" commercials. Jackie is currently seen in the series regular role of “Tony” in “Loudermilk” (DirectTV Audience Channel), which is Peter Farrelly’s directing foray into television.

He is also one of the proud winners of the prestigious San Francisco Comedy Competition, as well as a featured performer at the Montreal Just For Laughs Festival gala. He was chosen to perform at the U.S. Comedy Arts Festival in Aspen, Colorado produced by HBO.

Early on in his career, Jackie was discovered on stage in Boston by the Farrelly brothers, who have since cast him in back to back roles in “King Pin”, “There’s Something About Mary”, “Me, Myself And Irene” “Shallow Hal” and “Stuck On You.” Recently, Jackie has had prominent roles in “The Three Stooges,” playing opposite Kevin James in “Here Comes The Boom,” and in 2017's film “Special Unit.”

Jackie’s golf background, popularity from a national Phil Mickelson commercial, and relationships on the PGA and celebrity golf circuit make him an often requested headlining comedian for affiliated and corporate event entertainment including Bay Hill in Orlando FL, Bel-Air Country Club in Los Angeles CA, The Hideaway Golf Club in Palm Springs, CA, Trump Doral in Miami FL. Morgan Stanley, Hertz, IBM, Intel, and Yahoo to name a few. 

Jackie is truly a "comic's comic" whose refreshingly unique brand of sarcastic observational humor puts him in a class all his own, apart from the many derivative cookie-cutter comics plying the airways today. Audiences young and old appreciate his wit and rapid-fire "take no prisoners" delivery.

Kevin Flynn

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.

After graduating from the University of Massachusetts where he was captain of the soccer team, Kevin went on to play three years of professional soccer in the Major Indoor Soccer League (MISL). Following his soccer career, Kevin transitioned from pro-athlete to professional sportscaster, host and entertainer. He covered World Cup Soccer for Fox Sports, ESPN and ABC. Flynn’s Sports Figure’s show on ESPN received the POLK Award for excellence in children’s programming.

In 1996, Kevin became the host of The Discovery Channel’s Go For It, an extreme outdoor adventure show where he swam with sharks, jumped out of airplanes and scaled dangerous peaks. The show led Kevin to create his one-man show Around the Kitchen Table, which won the “Best of Fest” at the Boston Comedy Festival and HBO’s prestigious U.S. Comedy Arts Festival in Aspen.

Along with continually performing his stand-up, Kevin is also the co-founder and executive director of the Nantucket Comedy Festival and is producing a FIFA World Cup soccer movie for Imax titled One World One Ball. Flynn has been a regular guest on FOX News, The Strategy Room and hosts Plum TV’s Plum Daily Show on Nantucket during the summer.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents (Headliner) who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Dave Landau who will be performing with Key West local comedians.

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.

Dave served as co-host on “The Artie Lange and Anthony Cumia Show,” “The Anthony Cumia Show with Dave Landau,” and was a writer and on-air personality on Louder with Crowder. He is currently the co-host (along with “Quarter Black” Garrett) on a late-night sketch series called “Normal World” on Blaze TV. He regularly performs at clubs and theaters throughout the country.Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. As a top rising comic, Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening” and AXS.TV’s “Live at Gotham” 5 times. He was also a finalist on season 8 of “Last Comic Standing” on NBC.

Dave was brought in as 3rd mic on “The Artie Lange and Anthony Cumia Show.” When Lange departed, it became “The Anthony Cumia Show with Dave Landau,” where he co-hosted for two years. Dave was 3rd chair on one of the most popular conservative talk shows in the world, Louder with Crowder on Blaze TV, and regularly performs at clubs and theaters throughout the country.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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. Mack’s television credits

include Comedy Central's Live at Gotham, TBS’ Conan, Adult Swim’s Aqua Teen Hunger

Force, Fox’s Golan the Insatiable, and NBC’s Last Comic Standing, Last Call with Carson Daly,

and The Tonight Show starring Jimmy Fallon. When not touring, Mary spends way too much

time and money working on her vintage camper in the woods of Northern Wisconsin. To see

where Mack will be next or to browse her comedy albums, please visit

www.marymackcomedy.com.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Mary Mack, featuring Tim Harmston.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Kurt Metzger is one of the most talented writers and stand up comedians today. A Philadelphia native, Kurt started in the local scene with friends and comedians Kevin Hart and Big Jay Oakerson. 

Kurt moved on to New York, where he performed regularly at New York’s top comedy clubs, including Stand Up NY, Caroline’s on Broadway, Gotham Comedy Club, and the famed Comedy Cellar. 

A crowd favorite, he was accepted to Montreal’s prestigious Just For Laughs Festival, where he was a standout performer on their ‘New Faces’ show. 

Kurt has appeared on Comedy Central’s Live at Gotham, VH1’s Best Week Ever, CBS’s The Late Late Show with Craig Ferguson, and Showtime’s White Boyz in the Hood. He has also guest-starred in IFC’s Z-Rock as well as Comedy Central’s ‘Important Things with Demitri Martin.’ 

A prolific joke writer, Kurt served as a writer for Chappelle’s Show as well as the Comedy Central Roast series. He also became a series regular on Comedy Central’s animated Ugly Americans series, providing the voice of Randall Skeffington. 

Kurt released both his album Kurt Metzger Talks To Young People About Sex and his Comedy Central one-hour special “White Precious” to strong reviews from both comedy critics and fans.

Kurt lives in Los Angeles.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Kurt Metzger, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Dwayne Perkins, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Chad Daniels who will be performing with Key West local comedians.

With nearly a billion streams of his 6 albums to date, Chad Daniels is one of the most listened-to comedians ever. Originally from and still residing in rural Minnesota, Chad has been touring the country for over 20 years. He has made 6 late-night appearances and is one of only 13 comics to be featured on The Tonight Show with Conan O’Brien.

Chad co-hosts the hit podcast Middle of Somewhere with co-host Cy Amundson and recently launched his second podcast, PRETEND PROBLEMS, alongside his girlfriend Kelsey Cook. His latest special, MIXED REVIEWS, can be found on YouTube, and his kids tell him you can find him on Instagram and TikTok

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

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. His profile continued to rise with live performances on the Blue Collar Comedy Tour: The Next Generation, Vince Vaughn's Wild West Comedy Tour, Ron White’s Salute To The Troops, and the Showtime special Unsportsmanlike Comedy with Rob Gronkowski. He voiced the character of “Headphone Joe” on Disney’s Fish Hooks, played the part of “Brian” on the ABC sitcom Work It, was the host of Mobile Home Disaster on CMT, hosted a weekly radio show on Sirius XM, and has produced and appeared on numerous podcasts. In 2008, Cap's first full-length special, Meet Cap, premiered on Comedy Central. His second special, Come Inside Me, was released on Netflix in 2013. In 2018, Cap settled down in Las Vegas and performed almost 500 shows during a 2-year residency at Harrah’s. John Caparulo’s Mad Cap Comedy ran 5 nights a week until its unexpected demise as a result of the COVID-19 shutdowns. Now he’s back on the strip headlining exclusively at Jimmy Kimmel’s Comedy Club during the week, while touring nationally on the weekends. And on top of his commitments to being a great dad and a mediocre husband, Cap has written an outlandish comic book series based on his family. Cartoon Comic is available for purchase at JohnCaparulo.com

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents John Caparulo, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Patrick Garrity who will be performing with Key West local comedians.

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.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth 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.

Showtime at 8:30 PM. Doors at 7:30 PM.

Tickets purchased in advance will ensure that groups can sit together. Please let us know in advance if you will be joining another party.

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!