Upcoming Events

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!

Sam Tallent is a comedian, novelist and host of the Chubby Behemoth Podcast.

For the last decade, he has performed more than 45 weekends per year in North America, Asia, Australia and Europe.

His acclaimed debut novel, Running The Light, heralded as the definitive book on standup comedy, is soon to be a major motion picture. Random House is set to rerelease Running the Light in commercial paperback as well as his forthcoming follow up, Petillant Brut, in hardcover in 2025. His novella, ATTABOY, was published as an Audible Original.

Sam has two comedy specials: Waiting For Death to Claim Us (available on Amazon Prime) and The Toad’s Morale (available on the Matt and Shane’s Secret Podcast YouTube).

He also has a travel show, Wide World, on YouTube.

He lives in Detroit and cooks dinner for his wife every night.

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

Known for whip-quick wit and rollicking improvisations, Sam Tallent is one of the sharpest, most original rising talents in comedy today. He has been called "the absurd voice of a surreal generation" by the Denver Post, and, when not maintaining a "Black Flag esque tour schedule" (Savage Henry Magazine), Sam has worked alongside many of the biggest names in comedy, including Louis CK, Dave Chappelle, Doug Stanhope, Dana Carvey, Hannibal Buress and TJ Miller. Sam has performed at the Oddball Comedy Festival, High Plains Comedy Festival, Hell Yes Fest, the Chicago Comedy Expo and the NY Film and Television Festival. Sam regularly headlines his hometown club, the legendary Denver Comedy Works. He recently won his battle on Comedy Central's Roast Battle, and was seen on VICELAND's Flophouse as well as the Chris Gethard Show. His writing has been published on VICE.com. He lives in Las Vegas with his wife and his dog.

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 Joe List who will be performing with Key West local comedians.

JOE LIST is a stand-up comedian who wrote and stars in the movie FOURTH OF JULY (directed by Louis CK), which played theatres all over North America and is currently available on louisck.com. Joe’s previous 2 specials, THIS YEAR'S MATERIAL and I HATE MYSELF, have amassed over 11 million views on YouTube. Joe has performed on THE LATE SHOW WITH DAVID LETTERMAN, THE TONIGHT SHOW WITH JIMMY FALLON and has appeared multiple times on CONAN. He was a finalist on NBC's 'LAST COMIC STANDING, has his own half-hour special on Comedy Central, and also stars in season 2 of Netflix's THE STAND UPS. His albums 'So Far No Good' and 'Are You Mad at Me?' (through Comedy Central Records) can be heard all the time on Sirius Radio. Joe is the co-host of the popular weekly podcast 'Tuesdays with Stories' w/ Mark Normand and he hosts his own podcast MINDFUL METAL JACKET. He can be seen regularly at the Comedy Cellar in New York City.

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.

Comedian Bobcat Goldthwait first appeared on the David Letterman Show at the age of 20 and has an ongoing career as a writer, director, actor, voice actor, and stand-up. As a comedian, Bobcat has starred in numerous HBO/Showtime specials, performed in venues worldwide, and even went on tour as an opening act for the band Nirvana. Well-known for his roles in “Scrooged” with Bill Murray and as Zed in the “Police Academy” franchise, Goldthwait has become a well-respected Award-Winning Director, too. His directorial works include feature films World’s Greatest Dad, starring Robin Williams, Willow Creek, starring Bigfoot, God Bless America, Windy City Heat, Sleeping Dogs Lie, and the documentaries Call Me Lucky and Joy Ride. In addition to being a 4x Sundance Alumni, Goldthwait’s films have played internationally, including the Deauville Film Festival and San Sebastian Film Festival. 

Bobcat has been honored with the German Independent Honorary Award at the Oldenburg Film Festival for his collective works and was awarded “Filmmaker on the Edge” at the Provincetown Film Festival by his hero John Waters. His TV direction includes his series, Misfits and Monsters, Jimmy Kimmel Live, Community, Maron, Those Who Can’t, and many more. Goldthwait has directed numerous standup comedy specials for folks like Patton Oswalt, Marc Maron, Ron Funches, Kyle Kinane, Cameron Esposito, Mo Willems, Gary Gulman, Hari Kondabolu, Eugene Mirman, and Pete Davidson to name a few. Bobcat is currently working on several new film projects and has started his autobiography.

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Bobcat Goldthwait.

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 April Macie who will be performing with Key West local comedians.

April Macie was a finalist on NBC’s “Last Comic Standing” in 2006, has appeared on E! Entertainment, Sirius and XM Radio, Access Hollywood, Talk Soup, and HLN. April has appeared on the Howard Stern show where in 2008 she was voted the “Funniest and Hottest” comedian in America. She is also a regular guest on the Bob and Tom radio show and has toured with the Bob & Tom All-Stars. April has appeared on Showtime’s I Am Comic, Vegas Is My Oyster, Snoop Dogg’s: Bad Girls of Comedy, and was the host of the AVN Awards. April has also appeared on Comedy Underground with Dave Attell on Comedy Central and Jenny McCarthy’s Dirty Sexy Funny on A&E. She also gave a TEDx talk on turning pain into humor. Currently, April travels internationally as a headlining stand-up comedian.

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 Brendan Eyre who will be performing with Key West local comedians.

Brendan Eyre is one of the country's top young comedians. His laid back, observational style is a hit with audiences across the country. He has appeared on Late Night with Seth Meyers on NBC, Comedy Central, is a regular on Sirius Satellite Radio, and his comedy has racked up over 20 million views on TikTok (a platform he still doesn't really understand). Brendan's debut album Desiree was a hit on both the Billboard and iTunes comedy charts. Also, he has a blue belt in jiu-jitsu and his weight fluctuates wildly.

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!

Chris Trani is a fantastic comic from Chicago and a regular at Zanies, The Funny Bone, Laugh Factory, & more. Chris is the house emcee at The House of Blues where you can catch him every Thursday night in Chicago. He’s also shared the stage with Jon Lovitz, Ari Shaffir, Hans Kim, and Roy Wood Jr. of The Daily Show. Chris integrates all forms of comedy into his act: stand-up, storytelling, crowd work, one-liners; and if need be, can do it all in Spanish (kinda!).

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

Ahren Belisle is a software engineer and mental health advocate turned comedian. Born in Northern Ontario with cerebral palsy, Ahren is a mute comedian who uses his phone to deliver jokes. Ahren has over 800,000 followers on social media and has appeared on Kill Tony, JRE and America's Got Talent.

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

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!

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!

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!

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!

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!

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!

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.

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!

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!