Upcoming Events

Some comedians are also talented musicians. And most musicians have hilarious perceptions of our world. Caleb Hogan and Aubrey Urban bring comedy and music together in a one-of-a-kind show in Key West. Hosted by Caleb, a classically-trained concert pianist and comedian, this show also features some of the most beloved acts on the island singing punchlines and bringing never-before-seen (or heard!) entertainment to Comedy Key West.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

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.

Edgy, original, and hilarious is the consensus of his comedy. Bostonian Tom Dustin is the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off. He was so hilarious that the contest was closed to all future American contestants (USA! USA! USA!) He was also the winner of the Sam Adams Comedy Festival (Beer! Beer! Beer!) He's done Comedy Central, The Comedy Channel (Canada), local & national radio, podcasts, festivals, and roasts. His debut album, Dangerous Now, made it to the top 5 on iTunes and is played often on Sirius satellite radio. Tom is one of the best kept secrets in comedy; revered by famous comedians and mentioned frequently on the Joe Rogan Experience. Most recently, Tom was the subject of a documentary film, "Tom Dustin: Portrait of a Comedian", which highlights Tom's journey in standup comedy, his friendship with comedian/director, Joe List, and his issues with alcoholism and depression. It's hilarious, heartfelt, and honest; It gives a rare look into the comedians' lives, paths and struggles.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Mike Cronin is everything that is good about stand up comedy. A jovial, intelligent, and stupid man, he has spent the last 18 years traveling the globe giving audience’s the business. Through these years of road work, he has become one of the funniest, most well-respected comedians working today. In addition to headlining clubs all over, Mike also regularly opens for the likes of Tom Segura and Chad Daniels. You may have heard his name dropped on some of your favorite podcasts like Your Mom’s House, The Joe Rogan Experience, The Todd Glass Show, 2 Bears 1 Cave and Tuesdays with Stories. His first album, “Hot For Too Long”, debuted at #5 on the iTunes comedy charts, and his highly anticipated first comedy special entitled Thick Worm dropped November 30th of 2022. Nobody’s gonna make you laugh harder than Big Poppa Red!

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Myq “Mike” Kaplan has appeared on the Tonight Show, Conan, Letterman, James Corden, Seth Meyers, Comedy Central, Last Comic Standing, and America’s Got Talent. He has a half-hour special on Comedy Central, a one-hour standup special on Amazon called “Small, Dork, and Handsome,” and a new Dry Bar special called “Live From The Universe,” as well as two podcasts, “The Faucet” and “Broccoli and Ice Cream,” and a book of his jokes illustrated by Ramin Nazer called “Heart Brain Art Train.” His debut album, “Vegan Mind Meld,” was one of iTunes’ top 10 comedy albums of the year, and his newest album, “A.K.A.,” debuted at #1 and was called “invigoratingly funny” by the NY Times!

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Myke Herlihy is one of the most lovable jerks you’ll ever meet! After spending thirteen years behind bars, serving drinks not time, Myke now takes his bartender's wit to the stage. Whether he's discussing his failed relationships, ranting about the trials and tribulations of being an unwed father, or reminiscing over the insanity that was his childhood, Myke always manages to find the light at the end of the tunnel.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

In 2014, Drew began his stand-up career quickly making a name for himself around New England for his quick wit, voices, and unique style. After winning the Boston Comedy Festival in 2017, he began to perform comedy regularly around the country. 

In 2018, Drew won the Seattle International Comedy Competition followed by being selected to be a “New Face of Comedy” at the prestigious Just for Laughs Comedy Festival in Montreal in 2019.  Drew has since continued to headline comedy clubs across the US and Canada while making various types of online content earning millions of views. 
Drew has a special on Dry Bar Comedy and a set recorded with Don’t Tell Comedy. 

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Kalea McNeill is most known for her recurring character "Hanifa Downey" on CW’s Crazy Ex Girlfriend (season 4), and various television guest spots. In 2022 Kalea was selected for the prestigious Just For Laughs Comedy Festival in Montreal as a "New Face of Comedy".  Since then, she has taped with Comedy Central, Don't Tell Comedy and is a favorite at the Netflix is a Joke Festival and the Moontower Comedy Festival in Austin, TX. Her debut (Grammy Considered) comedy special "Sma'am" is now available on Amazon Prime Video, and can also be heard as an album wherever you stream.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

At under 5 feet tall, Lisa Corrao is the tiniest stand-up comedy-powerhouse you’ll ever meet. Lisa lights up stages from comedy clubs to comic cons worldwide. She's toured with legends like Patton Oswalt and the late, iconic Gilbert Gottfried, and even packs up her jokes to bring them to U.S. military bases around the globe. You’ve heard Lisa on Sirius/Xm as well as her podcast, "Safe Space” with Dana Snyder and Dino Stamatopoulos. You might also recognize her as the unforgettable Ramona the Witch on Nickelodeon’s "Every Witch Way." Now, she's spicing things up with her new, hilarious cooking show, "Lisa Loves Food!"

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Detroit native Mike Stanley is all of these things, but none, when put on paper, quite manage to serve the justice dealt by Stanley onstage. Yeah, he's pretty hilarious, but more than just coarse anecdotes about life, there's an enviable amount of heart and warmth behind Stanley's humor. 

Given his penchant toward brutal honesty, spiced up with a healthy dose of insatiable wit, it's not difficult to see why Stanley was named "Best Chicago Stand-up Comedian" in a Peoples Choice poll done by the Chicago Reader and "Best Detroit Comedian" by HOUR Magazine. 

Originally hailing from Detroit, and after spending a decade honing his craft in the Windy City of Chicago, Mike has been a touring headliner constantly, both domestically and internationally since 2006. Don't miss out on an incredible opportunity to catch the man in action - this high level of killer stand-up is too remarkable to sit out.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

After beginning his career in his home country of Ireland, Colum Tyrrell moved to New York City and quickly became one of the fastest rising comics in the scene. He is a regular at The Comedy Cellar, The Stand Comedy Club and Stand Up New York.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Henry Phillips has performed his stand up and twisted songs on Comedy Central Presents, Jimmy Kimmel Live, and as a regular on the Bob and Tom Show. You may also recognize him as “John the Server Guy” on HBO’s Silicon Valley, or as the star of the cult film “Punching the Clown”. But die hard fans will know him from his Youtube cooking series, Henry’s Kitchen, which has garnered millions of views worldwide.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Luis J. Gomez is a comedian, writer, podcaster and producer based out of New York City. He is most known for being one of the hosts of the popular Legion of Skanks. His television credits include NBC’s “Last Comic Standing”, Comedy Central’s “Roast Battle”, TruTV’s “Comedy Knockout”, two seasons of NBC Seeso’s “What’s Your F@%king Deal?!”, and more.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Cliff Cash got his comedy start in Wilmington, NC at Nutt St. Comedy, now Dead Crow Comedy Room. In the years since he’s gone on to win Port City’s Top Comic, Comedy Zone’s Almost Famous, and Best of the Fest at SLO Comedy Festival, and he’s been a finalist in Comedy Central’s UpNext and Standup NBC. He’s played iconic rooms from The Comedy Store in LA to the Comedy Cellar in New York City. He’s also headlined festivals like Altercation Comedy Festival in Austin and Tree Fort Festival in Boise. Cliff has been featured on Sirius XM Comedy Central, Rawdog, Laughs TV, Rooftop Comedy, and has a half-hour special from Dry Bar.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

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.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

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.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

The Boston Globe recently described Steve Bjork as “one of the top names” in New England stand-up comedy. He’s come a long way from his nights of frying up mozzarella sticks in the back room of a popular Boston comedy club. He was a college student, using that part-time job to study the craft of stand-up comedy by catching glimpses of the performers on stage.

Today, Bjork is a polished veteran of the highly competitive Boston comedy scene with crisscrossing tours of the country under his belt. His material is intelligent and accessible, but first and foremost, it is funny. Bjork takes everyday life and turns it upside down in a way that every demographic in any given audience can enjoy. A longtime favorite in nightclubs and casinos around the country, Bjork is also a highly sought-after corporate entertainer.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Forrest Shaw is a stand up comedian and writer (The Jim Jefferies Show). His stand-up has been featured on Conan and Live at Gotham. As an actor he has appeared on FX (Legit), Comedy Central (The Jim Jefferies Show), and Animal Planet (Swamp Wars). His album Mister Grizzly, recorded with Comedy Records, can be heard on Sirius/XM Satellite radio, Pandora, and Spotify. He is co-host of The Jim Jefferies Show Podcast.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Rich Vos has four specials on Comedy Central and over 100 television appearances. He has been seen on HBO, HBO Max, Netflix, Showtime, and Starz. Rich also produced and starred in the documentary “Women Aren’t Funny” and appeared in Judd Apatow's “King of Staten Island."

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Steven Rogers is a stand-up comedian known for his unique blend of wit, vulnerability, and sharp observational humor. His comedic style combines relatable mishaps, personal struggles, and endearing storytelling, often drawing from his own life experiences. Steven's fresh take on everyday challenges has earned him a devoted following and widespread recognition in the comedy world.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!

Mike Vecchione is a New York City based comedian who has been performing in NYC clubs and across the country for more than 20 years.

Mike has multiple appearances on The Tonight Show, as well as on Netflix, Comedy Central and Hulu. Mike was also in the movie The King of Staten Island, starring Pete Davidson and was a featured podcast guest on The Joe Rogan Experience. Mike currently has a one-hour comedy special available now on YouTube called, The Attractives, directed and produced by friend and fellow comedian, Nate Bargatze.

Please note:
There is a two item minimum.

Seating is first come, first serve. Arrive early to ensure preferred seats.

Please let us know in advance via email if you will be joining another party.

Love Seats
If you are purchasing Love Seats:
1 Love Seat = 2 tickets.
Please do not purchase (2) Love Seats, if you are coming with 2 people, as we cannot refund erroneous additional Love Seat 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.

During the Show

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!

Thank you!