Upcoming Events

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. Doors open at 7:30pm. Show starts at 8:30 PM. This is a free event! Arrive anytime after 7:30 to grab a seat.

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

James Scott Patterson is a Stand-Up Comedian and Writer. He has appeared on Comedy Central's Premium Blend and the New Faces Showcase at The Montreal Comedy Festival. He hosts a weekly comedy show in downtown Los Angeles called Nobody Move! In his spare time, he harasses political conservatives on Twitter by pretending to be a Leninist Revolutionary. He is not (and has never been) a member of a political organization.

James has lived in Key West for the last year, and has been an integral part of making Comedy Key West the amazing venue that it is. We're sad to announce he's leaving our weird little island, but we're going to celebrate the laughter he's brought to us all with this special going away show!

The show will feature our favorite local comics, and possibly involve a little roasting for the road. We'll all miss you, James.

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Kelly MacFarland, who will be performing with Key West local comedians.

As an experienced stand up comedian, Kelly has an extensive and well-rounded resume including comedy clubs, theaters, colleges and several television appearances.Kelly is currently touring clubs and colleges across the country and has entertained our US troops overseas. Kelly headlined the 2009 Boston Women in Comedy Festival, was first runner up in the 2009 Boston Comedy Festival, voted Best of the Fest 2010 Aspen Rooftop Comedy Festival, appeared in the Oddball Festival 2015 and performed at Boston Calling 2016 and 2017. Kelly has also appeared on Stand Up in Stilettos on the TV Guide Channel, Comedy Central’s Premium Blend and is the host of the web series, Fit or Fad for Scripps Network. Most recently, Kelly was part of the Top 100 Comedians of Last Comic Standing Season 9, appeared on AXS Gotham Comedy LIVE and won first in the professional category of the Ladies of Laughter 2016 competition.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Kato Kaelin, (an American actor, radio and television personality who was the most memorable witness in the O. J. Simpson murder case). Comedy Key West presents Kelly MacFarland, who will be performing with Key West local comedians.

As an experienced stand up comedian, Kelly has an extensive and well-rounded resume including comedy clubs, theaters, colleges and several television appearances.Kelly is currently touring clubs and colleges across the country and has entertained our US troops overseas. Kelly headlined the 2009 Boston Women in Comedy Festival, was first runner up in the 2009 Boston Comedy Festival, voted Best of the Fest 2010 Aspen Rooftop Comedy Festival, appeared in the Oddball Festival 2015 and performed at Boston Calling 2016 and 2017. Kelly has also appeared on Stand Up in Stilettos on the TV Guide Channel, Comedy Central’s Premium Blend and is the host of the web series, Fit or Fad for Scripps Network. Most recently, Kelly was part of the Top 100 Comedians of Last Comic Standing Season 9, appeared on AXS Gotham Comedy LIVE and won first in the professional category of the Ladies of Laughter 2016 competition.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

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

Thank you for reserving your spot for this special edition on Paint 'N Chug. If you are interested in hosting a private Paint 'N Chug event for your next birthday, company outing or any other special moment please email us today @ comedykeywest@gmail.com

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

Drew Dunn started performing comedy at the age of 21 and hasn’t looked back since. This NH based comic quickly established himself as one of the nation’s fastest rising comedians with his quick wit and unique point of view. He has been featured in comedy festivals across the country including the Johnny Carson Great American Comedy Festival as well as being named “Best of the Fest” in the 2017 Burbank Comedy Festival.

Drew has also won the Boston Comedy Festival in 2017 followed by winning the Seattle International Comedy Competition in 2018. Most recently Drew was in featured as a New Face of Comedy in the 2019 Just for Laughs Comedy Festival in Montreal.

He now headlines comedy clubs and colleges across the US and Canada along with making various types of online content.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Gateway Comedy Tour!

Stand-up comedians tell you some jokes, then they get SUPER HIGH and attempt to tell you some more.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 The Brothers from Another Mother Comedy Tour, who will be performing with Key West local comedians.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Kevin Bozeman who will be performing with Key West local comedians.

With a smooth and clever style, a great smile, and a contagious laugh, Kevin Bozeman has been entertaining in clubs and colleges across the country. In 2000 he was the winner of the Midwest region of the HBO “Comedy Competition” and flew to Los Angeles to compete as a finalist. He performed on Comedy Central’s “Premium Blend” in 2003 and finished 2nd in the Boston Comedy Competition in 2005. He was a semi-finalist on NBC’s “Last Comic Standing” in 2015. Kevin has appeared on Comedy Central, NBC, CBS, and Fox. His Dry Bar Comedy Special, “Clean & Unfiltered” has over 7 million views

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

One of Comedy Key West’s early students, Stephanie Kaple first tried standup in 2016 and has been making crowds since. Now based in Savannah, Georgia she regularly performs around Savannah with the Savannah Comedy Underground and Savannah Comedy Revue. Stephanie is the 2021 Savannah Comedy Slam Winner and 2019’s 1^stRunner Up in the Florida Funniest Female Contest, part of the Flamingo Comedy Festival. Prior to this, her greatest comedic achievement was being named Class of 2000 “Wittiest Girl” at Fairborn High School, she still has the trophy on display in her house. Stephanie followed this with a 15-year award hiatus until she won Key West Story Slam Grand Slam in 2015. Stephanie has opened for Howie Mandel at the Key West Theater and has been featured in Keys Style magazine. Stephanie performed in the 2020 New York Underground Comedy Festival, the Miami Buskerfest 2019, Flamingo Fest Winter Showcase 2019, and in the Florida’s Funniest Females showcases. Stephanie has appeared on the Real Housewives of Orange County as “the driver” during the Key West cast trip… and they were that crazy in person. This will be Stephanie’s first return to Key West and she is excited to be back with her Comedy Key West crew. This special one-night-only show will promise two things: great shoes and tales from life where the Arby’s is only a moment a way! Stephanie will also be performing at Mister Z’s where she will eat her weight in cheese fries.

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

Are you tired of seeing the same old thing at every comedy show you go to? Looking for some more perspective to your laughter? Yearning for change? Big Girl Pants feels the same way and we are here to bring it! This isn't just your ordinary stand up show, and comedy isn’t just for the boys anymore. Come join us and watch as we challenge our male comedian counterparts to put on THEIR Big Girl Pants and fight for stage time by answering questions about women. The more they know, the more stage time they get. There's always a female headliner and a good time!

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 and Sarah Tollemache, who will be performing with Key West local comedians.

Joe List began his comedy career in Boston, Massachusetts in 2000 just weeks after graduating from high school. Since that time he has been featured on The Late Show with David Letterman as well as multiple appearances on Conan. He’s featured in Season 2 of The Netflix Series “The Stand Ups”. In 2015 List was a finalist on NBC's Last Comic Standing and had his own Half Hour comedy special on Comedy Central. His albums 'So Far No Good' and 'Are You Mad at Me?' can be heard regularly on Sirius Radio. List is also the co-host of his own popular weekly podcast 'Tuesdays with Stories'. When not headlining comedy clubs all over North America, List is a regular at the Comedy Cellar in New York City.

Sarah Tollemache is a stand-up comedian, writer and podcast host. She has been featured on Comedy Central as well as NBC’s ‘Last Comic Standing’. In 2017 she appeared on ‘The Late Show with Stephen Colbert’. Tollemache followed that up with another late-night appearance, this time on ‘The Late Late Show with James Corden’. She has also appeared on Comedy Central’s ‘Roast Battle’ and Gotham Comedy Live. When she’s not touring comedy clubs around the country Sarah can be seen regularly at The Comedy Cellar and New York Comedy Club in New York City. Sarah is also the Co-Host of the popular weekly podcast ‘Vadge’.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

Jimmy Shubert has built an impressive resume as an actor, both in film and on television. As a comedian, he is one of the busiest comedians working today. After becoming a finalist on NBC’s “Last Comic Standing” and, being seen on Comedy Central as the closing act on Dave Atell’s Comedy Underground. He also just wrapped post-production on his brand new hour special entitled “Zero Tolerance” – soon to be seen on a premium cable network.

From headlining A list comedy clubs, casinos, theaters across the country. Shubert’s New-hour special ‘Zero Tolerance” is a theatrical presentation of Shubert’s stand-up persona of a blue-collar working man’s man. He combines the outlook of a modern-day Archie Bunker with an utterly real-world sensibility to create signature pieces of comedy, on Therapy cats, Smart Phones, Male grooming and, the dumbing down of America. Shubert loves playing the part of a pop culture Iconoclast.

In television, Shubert is also known for his recurring role on “King of Queens” for five years and several appearances on “Entourage”. Jimmy has a wide range as an actor and has played everything from a prison guard in a hostage crisis to a murder victim on “Monk.” He’s worked with such marquee names as Brad Pitt, Angelina Jolie, Charlize Theron, Katie Holmes, Kevin James, James Caan, and the late Robin Williams. On the small screen, He recently did a guest star on IFC’s ”Maron” ABC’s “Back in the game” with James Caan, on the CBS comedy “2 Broke Girls”, He played Betty Whites' neighbor. He appeared on Disney’s hit show “Zeke and Luther” as Bobby Dicey”-World’s Greatest Daredevil, and “Barely Legal” a pilot presentation about a dysfunctional family law firm, other TV credits include ” “Heist,” “The Loop,” “ER,” “Reno 911,” “Rude Awakenings,” “Angel,” “Lucky,” “New Car Smell,” “Sonny with a Chance” and “Youth In Revolt.”

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Jim Colliton who will be performing with Key West local comedians.

Jim Colliton is a top shelve, headlining, stand-up comedian – Jim is also a master of the corporate show. Corporate shows are a different kind of show. The comedian must be funny within the corporate boundaries, blending funny material while not offending anyone or any group. Everyone needs to leave happy; the employees, Human Resource and the person managing the event. Jim does that!

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 American Laugh-Off), Comedy Key West presents Steve Crane who will be performing with Key West local comedians.

Steven Crane is taking a break from his stupidly busy schedule to giggle out some sillies for you folks! He attended The Second City Training Center in Chicago graduating from the Improv and Writing programs but dropped out of the Stand-up program when his parents figured out he was attending a Comedy School. Steve hosts the Drunk Spelling Bee at Mary Ellen’s on Monday nights and is often a host at the Comedy Key West Tuesday Open Mics. You can also catch a glimpse of Steve at many Burlesque shows, though it may not be a glimpse you want! Come see Steve attempt funny! Comment below if you read these.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Kenny Rogerson, who will be performing with Key West local comedians.

KEN ROGERSON, the funniest man you’ve never heard of, started his comedy career working the Chicago club circuit and at the famed Second City. After touring with the improvisation troupe The Comedy Rangers, Ken moved east and became part of the exploding Boston comedy scene of the 1980’s, where he honed his standup act to a fine edge “…sharp enough to cut the head off a rabbit at thirty yards.”

Fresh off his second nationwide “Rescue Me Comedy Tour” with Denis Leary, Kenny is a favorite in clubs, theaters and on the large and small screen. You may have seen him as “Kevin the Biker Fireman” on F/X’s hit show “Rescue Me” starring Denis Leary and as “Pat the Cop” on ABC’s “It’s All Relative” with Lenny Clarke. He has also made numerous other television appearances on such shows as NBC’s , “Late night with Conan O’Brien”, “The Late Show with David Letterman”, “Comics Come Home” for Comedy Central and Showtime’s “A Pair of Jokes” just to name a few. Rogerson has also appeared at The Chicago Comedy Festival and TBS’s The Comedy Festival in Las Vegas.

The Boston Herald proclaimed, “He makes the absurd seem logical” and Las Vegas Magazine wrote, “As far as pure stand-up goes, it doesn’t get any better than Rogerson.” Michael Blowen of the Boston Globe raved, “He is fall down on the floor funny! Why doesn’t this guy have his own show?” Nick Zaino, also from the Globe says, “He’s as funny a comic as Boston has produced.”

A writer, sketch player, actor and comedian, Rogerson wrote and starred in comedy film pieces on Fox Television Network’s “Sunday Comics” and has made film appearances in “Fever Pitch” and “There’s Something About Mary.”

If these aren’t enough reasons to catch his act, then how about this:

Come to his show or he’ll come to your house!

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 close to a billion streams of his 5 albums to date, and averaging a million more every week, Chad Daniels is one of the most listened to comedians of all time.

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 to date and is one of only 13 comics to be featured on The Tonight Show with Conan O’Brien. His previous album Footprints on the Moon was the most streamed comedy album of 2017.

Chad’s third stand-up special and fifth album, Dad Chaniels, was released on Amazon in 2019 and his hugely popular podcast, Middle of Somewhere with co-host Cy Amundson, is released weekly.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Dan Crohn, who will be performing with Key West local comedians.

Dan Crohn has been performing stand up comedy in and around Boston for years. His jokes can be heard on XM Radio and he has been a guest on the popular podcast WTF with Marc Maron. A semi-finalist in the Boston Comedy Festival and the Laughing Skull Festival, Dan's stories of family and friends have entertained audiences from all over the country. Dan was named one of the top 100 comics for Season 9 of Last Comic Standing. His former day job of teaching 4th graders has provided him with endless amount of material. He has wanted to be a comedian since the age of eight when he stumbled upon his Father's Henny Youngman records.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Rocky LaPorte who will be performing with Key West local comedians.

Rocky LaPorte’s appeal comes from his everyman, streetwise style of comedy. Delivering laughs in his trademark Brooklyn accent, he has become one of the most sought after comedians in the country, and he just recently appeared on on the season 8 of NBC’s Last Comic Standing! Rocky received 5th place out of 10 contestants. A former Chicago truck driver and dock worker, Rocky has accumulated a slew of performances throughout his career, including being a featured comic on Showtime‘s The Godfathers of Comedy, a special starring five of America’s most hilarious Italian-American comics. On the big screen, he has been seen in two Tim Allen movies – Crazy on the Outside and The Shaggy Dog.

Rocky traveled with Drew Carey to Iraq to entertain the troops and was seen on the Showtime special Patriot Act: A Jeffrey Ross Home Movie. Rocky has filmed his own Comedy Central Presents special and was voted the network’s second most popular comedian in a nationwide poll. He has performed on The Tonight Show with Jay Leno, and appeared on A&E‘s Evening At The Improv and VH1‘s Stand-Up Spotlight, along with sitcom appearances on Cheers and his own NBC pilot called the Rocky LaPorte Show.

Rocky has opened for the likes of Garry Shandling, Drew Carey, Tim Allen, Louie Anderson, Hootie and the Blowfish and the Righteous Brothers, just to name a few. His clean, blue-collar style of comedy continues to increase in popularity as he travels the country.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Doug Stanhope.

SPECIAL EVENT

IF TICKETS FOR THIS EVENT ARE SOLD OUT ON THIS SITE- Additional tickets may be available by clicking HERE

Parties may be combined; You may be sat together with other guests.

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.

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!

Tom Rhodes is a world traveling comedian who is now celebrating his 30th year as a stand up comedian. The New York Times describes him as “A mostly natural intellect with a knack for reporting the harsh realities of life with a dark and absurdly optimistic cynicism.”

An adventurer forging his own path, Rhodes has built a career that not only includes stand-up specials, a sitcom, a travel show, a late night talk show, numerous live CD’s & DVD’s, his critically acclaimed podcast Tom Rhodes Radio, as well as being a travel writer for the Huffington Post.

Fresh from releasing his new hour special Light Sweet Crude on Netflix Rhodes has had a long raucous career covering every corner of the globe. His latest TV recording on Comedy Central Comedy Underground with Dave Attell will be airing in 2014. In 2012 Rhodes was featured in the Showtime stand-up series, Live From Amsterdam (2012). His three half hour stand-up specials include two Comedy Central Presents… (2009 & 2001) and Raw, recorded in Stockholm for Swedish television (2009). He had his own sitcom television show on NBC called Mr. Rhodes (1996 – 1997), his own Late Night Talk show on Dutch television Kevin Masters starring Tom Rhodes (2002 – 2003), and traveled the world as a TV presenter on the Dutch travel program Yorin Travel (2004).

His latest LIVE recording as a double CD Colossus of Me released in 2012. In 2009 Laughspin.com named his DVD Rhode Scholar the Number One Comedy DVD of 2009. As a featured travel writer for Huffington Post his travel story ‘A Tragedy, A Miracle And A Brawl…Welcome to Ireland’ got awarded by the Huffington Post one of the Top 10 Best Travel Stories of 2011.

His podcast Tom Rhodes Radio was named one of the Top 10 of Best Podcasts of 2011 by Matador Network and was praised as the best newcomer in The Onion AV’s Club (December 2012). Since 2013 Tom Rhodes Radio joined Bill Burr’s & Al Madrigal’s All Things Comedy Network. Tom has been a guest on The Joe Rogan Experience (#248, 364, 420 & 500), The Adam Corolla Show, Marc Maron’s WTF, Aisha Tyler’s Girl On Guy, London Real, The Artie Lange Show, Ron & Fez Show, NPR Snap Judgment.

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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 Tom Simmons who will be performing with Key West local comedians.

Tom Simmons was born the only boy and middle child to a close-knit family that moved a lot. At a young age Tom immersed himself in reading, from the imaginative world of comic books to the authentic world of non-fiction novels; anything was fair game. Tom questioned everything and everyone, respectfully... but with absolutely no respect at all.

Now a 21 year veteran of stand-up comedy, Tom has remained a power player in an industry where comics fail, and often. For over two decades he has travelled on national tours, headlined comedy-clubs, won comedy festival awards and made numerous TV appearances on major networks including: Comedy Central, Showtime, BET, Bounce TV, Comedy.TV, Laughs on FOX, and COMICS Unleashed.

A self-described contrarian, his style of comedy will remind you of that funny friend who has you laughing so hard your stomach hurts. Pulling from everyday situations as a father and husband, Tom finds comedy wherever he takes a good look. He likes to make stupid people and smart people laugh because he sees himself as both.

Whether it be a corporate retreat, a cruise ship deck or a morning show, this (predominately) liberal comedian has a knack for making people of all walks laugh pretty hard in literally any situation. Tom aims to be that comedian that speaks the truth and says what people can’t, in a funny way of course.

Tom Simmons is blazing his own path (he never moved to NY or LA, contrary to nearly everyone’s advice) and creating a career to die for. If you can’t see him in person (which you will regret), Tom’s comedy albums are available on Amazon and iTunes, he has a Pandora channel, and appears on the popular segment "Mad as Hell," on the FOX syndicated show, LAUGHS. Tom also writes and shoots the reoccurring web series called “So Then There's This," where he delivers his unique take on current events, pop culture, and more.

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

Unabashed Menopausal New Yorker and self-proclaimed lifelong bachelorette, Lynne Koplitz offers advice to men and comfort to women when dealing with hormones. Defender of the crazies and all who don't have children, she is a reporter of the truth or rather her truth. As a professional comic for 20 years, she gives us both male and female perspectives and tips on how to get along or at the very least survive one another. If you wish your girlfriend would talk less; your husband would stop calling you crazy; or If your Mom feels like an alien you can't relate to, then sit down and listen to the advice of ole Auntie Lynne who shoots from the hip. Koplitz is the Millennial version of Auntie Mame, if Auntie Mame said the F* Word a lot and talked about oral sex sometimes. You might be advised to wait till your church group leaves to start watching her. Koplitz comes by her point of view quite naturally and understandably given her mentor for over a decade was the late great Joan Rivers. Having appeared on several televisions shows with Rivers and costarring with the Legend, it only seems appropriate that Koplitz dedicate her Netflix Special Hormonal Beast To Rivers. Koplitz most recent credits include opening for Louie CK on the Road for the better part of 2017 and twice at Madison Square Garden; and the honor of opening for Chris Rock in 2017 and appearing in his hit movie, “Top Five”. When she is not on the road, Koplitz can be found canoodling with her 6 month old puppy in her Greenwich Village apt or performing at the Village's famed Comedy Cellar on the weekends."

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!

Emma Willmann is one of New York City’s top comedians, and perhaps one of the only dyslexic-gender-wiggly-comics-with-ADHD from Blue Hill, Maine. In the third grade, Mrs. Weller would bribe Emma with the chance to tell a story at the end of every class if Emma promised to stop talking to the other classmates. Now, Emma gets to tell stories nightly at The Comedy Cellar, on Netflix’s: The Comedy Line Up, Comedy Central, and is one of the few comics ever to have multiple appearances on The Late Show with Stephan Colbert. All of which has earned Emma a spot on Caroline’s 10 Funniest Comics, Just For Laughs: New Faces, and TimeOut’s 10 Funniest Women in NYC. Emma’s mom is “really proud of all of this but doesn’t like comedy.”

Additionally, Emma is an actor and writer best known for playing the role of Beth on Crazy Ex-Girlfriend and also featured on Paramount Plus’s The Good Fight, Judd Apatow’s Crashing, MTV, and TruTV. Emma also has a chart-topping podcast, Inside The Closet and is a regular on The Taylor Strecker Show.

Emma tells stories everyday on Instagram and TikTok, several of which have gone viral and earned a total of 260,000 followers (although we’re pretty sure Mrs. Weller isn’t one of them). From peanut butter to porn preferences, Emma loves talking about everything and is known for the unique ability to authentically connect with all types of audiences, even the occasional heckler.

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

Please note:

If you are purchasing Booth Seats, 1 ticket = 1 Booth, which is good for two people. Please do not purchase (2) booths if you are only coming with (2) people.

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!