Upcoming Events

Christine Hurley is a favorite on the comedy festival circuit. She recently performed on the “Masters Show” at the Montreal Comedy Festival. Christine works regularly at the casinos of Aruba, Las Vegas, Florida and the MGM franchise! Christine Hurley’s all time favorite event is Denis Leary’s annual “Comics Come Home” show at the Boston Garden!

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

Two National Headliners in One Big Show

Special Tuesday & Wednesday Comedy Tour +=

Comedy Key West Presents: A Brother From Another Mother

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Join us Night, April 20 & 21 at 8pm.

This special event comedy tour features not 1 but 2 amazing national headlining comedians.

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Jackie Flynn has emerged as one of the funniest & most talked about comedians to come out of Boston. Jackie has made a name for himself in the film industry being casted for roles in Kingpin with Woody Harrelson; There's Something About Mary with Cameron Diaz; Me, Myself & Irene with Jim Carrey; Shallow Hal with Jack Black & Hall Pass with Owen Wilson.

Kevin Flynn's career as a comedian took off after winning the Boston Comedy Riot, where he then began appearing on numerous comedy specials. He has since added several films & television credits to his name appearing in The Heartbreak Kid with Ben Stiller; Me, Myself & Irene with Jim Carrey; Osmosis Jones with Billy Murray, and Sex And the City.

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- Thursday April 20th at 8pm

- Friday April 21th at 8pm

Limited to 50 seats per show.

Reserve your tickets asap!

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 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!

Ron Feingold is an a capella corporate and cruise ship entertainer residing in Florida and also performs at his favorite comedy clubs around the country. Check out the show because you won't see or hear anything like this anywhere

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 Best Drug Stories Edition.

No matter how long you’ve lived in Key West, how you make your living, or whether or not you’ve seen the green flash, we’ve all had a story or two to tell...if we can remember them.

We invite you to come tell your best drug related stories.

Free Admission for Storytellers - Sign-up between 6-8pm during our Happy Hour or send an email to comedykeywest@gmail.com to let us know if you'd like to participate.

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 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.

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!

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.

Comedy Key West presents a weekly variety show featuring local and touring performers of stand-up, music, sketch comedy, videos, characters, storytellers, game shows, prizes, and more. Hosted by veteran comedians Tom Dustin (Yuk Yuks $25k contest winner), and James Scott Patterson (Comedy Central). Every show is unique, and a blend of the scripted and the improvised. Join us for some drinks, laughs, and surprises.

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!

Raanan Hershberg is a loud, neurotic Jew from Louisville, KY. He recently made his national television debut on The Late Late Show with James Corden. In 2017, he was a finalist in StandUp NBC and The Laughing Skull Festival in Atlanta, GA. In 2018, he was a finalist in the Boston Comedy Festival.

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!

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.

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!

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."

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 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 Canadien Laugh Off), Comedy Key West presents Corey Rodrigues who will be performing with Key West local comedians.

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!

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

Tony V was named “Funniest Person in Massachusetts” by Showtime television. He followed this achievement with several performances on HBO, the Arts and Entertainment Network, Comedy Central, and MTV. Spending time in New York and L.A. paid off with multiple highly acclaimed appearances on Late Night w/ Conan O’Brien, Comedy Central’s Tough Crowd w/ Colin Quinn, and several sit-coms including Seinfeld, Boston Common, The Single Guy, and Dr. Katz Professional Therapist. Having proven himself a solid comic actor Tony then tackled dramatic roles on television working with such notable actors as Eric Roberts, Ice T, and James McDaniels from NYPD Blue.

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 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 Robbie Printz who will be performing with Key West local comedians.

A fixture on the Boston comedy circuit, Robbie Printz got his start in 1988 and has been performing ever since. He made the rounds on the Cable Comedy shows, including MTV, A&E, and Comedy Central. He won the Boston Comedy Festival and was named the Best Comedian in Boston, by the Improper Bostonian.

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 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!