Upcoming Events

Join us for an intimate outing as we journey into original music by Les Greene & River. Hear the stories behind the lyrics as we showcase songs you know & love as well as experience a variety of new originals.

*Please Note: Due to our limited seating capacity of 50 seats, we are offering groups the opportunity to reserve your spot for the show at only $5 per person. This will guarantee your spots for the show. 100% of this will go to the artist. Free admission is available at the door for the remaining spots but not guaranteed.

We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

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 7:00 PM.

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

Please Note: We ask that all attending guests wear a mask upon entering our business and when not seated.

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:
We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep conversation 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!

Your host Lance Berry received nomination & was a Finalist for a “Bubba Award” (2018) in Best Artist, alongside Wyland and Rick Worth. There is a 30 guest maximum. Please reserve your seats today!

Please Note:
We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 7:00 PM. Doors at 6:00 PM.

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

Thank you for reserving your spot for this special edition on Pain '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

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

Please Note:
We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep conversation 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!

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’.

We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep conversation 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!

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:

We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep all conversation 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!

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:
We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep conversation 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 Gold Coast Comedy Allstars. Join us on Sunday, February 28, 2021, as some of the best comedians from South Florida are coming down to Key West for one night only.

Featuring Jackie Sanchez, Nadeem Awad, Nik Macik, and Steve Lamm.

Jackie Sanchez

2019 Winner Miami Ultimate Comedian Contest Jackie has been a regular host at both the Miami and Palm Beach Improv as well as headlining and featuring on shows all over South Florida.

Nadeem Awad

A 2019 Runner-up in Florida’s Funniest Comedian Contest, Nadeem Awad has been a longtime house favorite at the Palm Beach Improv and recently started touring featuring for the Legendary Jimmy Schubert.

Nik Macik

After starting his comedy career with Comedy Key West Nik moved up to South Florida recently taking 2nd place in the 2020 Spill The Beans Comedy Contest and has been featuring and headlining showcases all over South Florida as well as taking to the road with his own Gold Coast Comedy Tour

Steve Lamm

2019 Underground Legends Contest 2nd place finisher has been a Palm Beach Improv regular and local favorite featuring in shows all over South Florida delivering some of the best one-liners you’ll hear this year.

Please Note:

We ask that all attending guests wear a mask upon entering our business and when not seated.

Showtime at 8:00 PM. Doors at 7:00 PM.

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

We ask that you please keep 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!