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(305) 985-7370

Comedy Key West

218 Whitehead St. Unit 5

Key West FL 33040

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Menu
  • Tickets
  • Calendar
  • Menu
  • About
  • Local Comedians
  • Booking
  • Pictures
  • Store
  • Contact
  • Newsletter Sign Up

Upcoming Events

February 07 - March 28

The Madhaus Open Mic

Bring your best standup routine or watch us crash and burn. The Madhaus Open Mic is the best comedy open mic in Key West because...it's the only one! 

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Tue, Feb 7, 2023
8:30 PM
Tue, Feb 14, 2023
8:30 PM
Tue, Feb 28, 2023
8:30 PM
Tue, Mar 7, 2023
8:30 PM
Tue, Mar 14, 2023
8:30 PM
Tue, Mar 21, 2023
8:30 PM
More Dates Available
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Likely To Sell Out! Special Event
February 08 - February 09

Michael Winslow

Michael Winslow “The Voicetramentalist"

Michael’s quest for hilarity began in Boulder, Colorado at a club known as Tulagi’s, famous for its legendary acts such as Tommy Bolin, The Doors, and even Jimi Hendrix himself!

This connection with Jimi would continue throughout Mike’s career as he would open for Italian Rock Fusion Band “Nova”, with a rendition of Purple Haze that was nothing short of magic, no one can imitate a guitar with just their voice quite like him. His vocal talent was apparent, but Michael wanted to take it further and start a career as a professional entertainer.

Michael hit the road with just the clothes on his back and a dream, taking Venice Beach by storm. He auditioned for just about any act he could find, and his hard work came to fruition when he auditioned for the Gong Show hosted by Chuck Barris. From the earnings he made from that gig he was finally able to purchase a car to perform at even more clubs. It was at the Evening at the Improv Club, owned by Bud Friedman, in which he would become a household name in Los Angeles.

It was in 1984 where Michael would get his big break from Director Hugh Wilson and Producer Paul Manslanski, creators of the cult classic Police Academy, as they saw his talent first hand at the Long Beach Theater. They saw the raw talent that Mike brought to the table and immediately wrote him into the script, paving his way for a career in cinema, also taking a role in Mel Brooks’ Space Balls! 

While his talent on screen is apparent, he is also a skilled voice actor appearing in commercials for companies such as Geico, but also hit television series such as Family Guy and Robot Chicken. Mike’s versatility really allows him to play any voice role.

Michael is a true master of his craft, an artist. He can recreate any sound known to man and more, limited only by his imagination, making him a must see entertainment staple which keeps him quite busy. He has recently finished up a comedy special on the Starz Network with Jimmy Walker, but he also runs a podcast where you can hear he his unique takes on life and comedy known as the Noize Podcast available on [put the platform here]

Mike’s next big projects involve various animated shows with large network interest, as well as variety shows in Vegas! You won’t want to miss out on any of these surefire classics.

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

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Wed, Feb 8, 2023
8:30 PM
Thu, Feb 9, 2023
8:30 PM
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February 10 - February 11

Ari Shaffir

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

Ari Shaffir is best known for the storytelling show he created and hosted on Comedy Central called "This Is Not Happening." His last Netflix special, Double Negative won a Grammy for best comedy special before the award committee realized it was too filthy and didn't represent the high standards that the Grammy's has long since stood for so the honor was stripped from him. Ari has had numerous appearances on the Joe Rogan Experience podcast, as well as WTF with Marc Maron, The Adam Carolla show, Your Mom's House. His own podcast, Ari Shaffir's Skeptic Tank is a chart topper that comes out every week wherever you watch or listen to podcasts. He is the reigning president of the LOS podcast to which he has no affiliation. And he placed first in the non-steroid category of the legendary Sober October challenge, which he also destroyed shortly thereafter.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Fri, Feb 10, 2023
8:30 PM
Sat, Feb 11, 2023
8:30 PM
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Special Event
February 13 - February 27

Paint 'N Chug

Special Event In Key West 🎨 +🍷=😆

The 'oh so popular Wet Paint Comedy Hour (or 2) Hosted by Lance Berry-Matic (LB Art Inc) is BACK by popular demand. Join us for another fun filled remix of painting, comedy, games & more!!

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Your host Lance Berry received nomination & was a Finalist for the “Bubba Award” (2018) in Best Artist, alongside Wyland and Rick Worth. Lance was again nominated for this year’s best artist award in Key West.

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Join us & see why we have sold out almost every Paint ‘N Chug event. We are very fortunate to be able to offer additional events with select dates. Lance shows you step by step how create masterpieces of your own.

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There is a 40 guest maximum.

Please reserve your seats today!

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Mon, Feb 13, 2023
7:00 PM
Mon, Feb 20, 2023
7:00 PM
Mon, Feb 27, 2023
7:00 PM
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February 15 - March 29

The Local Showcase

Comedy Key West presents the Local Showcase - Key West's favorite local comedians with some special out-of-town guests rocking the stage for one night only.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Wed, Feb 15, 2023
8:30 PM
Wed, Mar 1, 2023
8:30 PM
Wed, Mar 8, 2023
8:30 PM
Wed, Mar 15, 2023
8:30 PM
Wed, Mar 22, 2023
8:30 PM
Wed, Mar 29, 2023
8:30 PM
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February 17 - February 18

Dave Landau

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

​Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. As a top rising comic, Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening” and AXS.TV’s “Live at Gotham” 5 times. He was also a finalist on season 8 of “Last Comic Standing” on NBC.

Dave was brought in as 3rd mic on “The Artie Lange and Anthony Cumia Show.” When Lange departed, it became “The Anthony Cumia Show with Dave Landau,” where he co-hosted for two years. Dave is currently 3rd chair on one of the most popular conservative talk shows in the world, Louder with Crowder on Blaze TV, and regularly performs at clubs and theaters throughout the country.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Fri, Feb 17, 2023
8:30 PM
Sat, Feb 18, 2023
8:30 PM
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Special Event
February 19 - February 22

Joe Matarese

Joe Matarese as seen on The Howard Stern Show, WTF with Marc Maron, The Late Show with David Letterman, Comedy Central Presents Joe Matarese (His Own 1/2 Hour Special), The Late Late Show with Craig Kilborn and Craig Ferguson, Last Comic Standing, The Better Half, and Chelsea Lately. Joe was also featured on America’s Got Talent, where he received a standing ovation from all four celebrity judges, Joe hastwo comedy specials, Medicated, and The Poster's Wrong. In the Spring of 2023, he will be releasing his third comedy special called Mullets and Mixtapes. Joe has seven standup albums currently in rotation on Sirius XM, including; Quiet Please, Fixing Joe, Disconnected, When A Comedian Attacks, Medicated, The Poster’s Wrong, and Completely Present.

To learn more about Joe, visit his website https://www.joematarese.com

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

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Sun, Feb 19, 2023
8:30 PM
Tue, Feb 21, 2023
8:30 PM
Wed, Feb 22, 2023
8:30 PM
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February 23 - February 25

Patrick Garrity

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

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:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Thu, Feb 23, 2023
8:30 PM
Fri, Feb 24, 2023
8:30 PM
Sat, Feb 25, 2023
8:30 PM
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March 02 - March 04

Andy Woodhull

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

Andy Woodhull has appeared on The Late Late Show with James Corden, Conan, Live at Gotham and The Half Hour on Comedy Central. In 2014, he was the first comedian to make his network television debut on The Tonight Show Starring Jimmy Fallon. His Dry Bar comedy special on YouTube has over 9 million views. All five of his comedy albums are in rotation on Sirius Satellite Radio, and his jokes have played over 40 million times on Pandora. Most recently, Andy worked as a writer on SYFY’s The Movie Show, and was featured in two episodes.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Thu, Mar 2, 2023
8:30 PM
Fri, Mar 3, 2023
8:30 PM
Sat, Mar 4, 2023
8:30 PM
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March 09 - March 11

Paul Nardizzi

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

Paul Nardizzi began his comedy career in 1990, quickly becoming a Boston area favorite and a national headliner within four years. Paul Nardizzi has made numerous appearances on Late Night with Conan O'Brien, Comedy Central, NESN Comedy All Stars. Paul also won the Boston Comedy Festival Competition, HBO's U.S. Comedy and Arts Festivaland is one of the most requested acts on XM Satellite Radio. As a top stand up comedian in Boston and the New England Area, he is known for his rapid-fire comedy, ability to engage the crowd, and tailor material to audiences. Paul can be seen performing in clubs nationwide in addition to providing corporate entertainment and working at charity events and parties. 

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

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Buy Tickets
Thu, Mar 9, 2023
8:30 PM
Fri, Mar 10, 2023
8:30 PM
Sat, Mar 11, 2023
8:30 PM
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March 16 - March 18

Ryan Donahue

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

Ryan Donahue is a comedian, actor, and writer based in NYC. After making his network television debut on Jimmy Kimmel Live!, he’s made multiple appearances on HBO’s Crashing and Pause with Sam Jay, where he is also a staff writer. He’s performed at the Just For Laughs Festival in Montreal, The Eugene Mirman Comedy Festival, and The Great American Comedy Festival held in honor of Johnny Carson. Ryan has opened for Norm Macdonald, Tig Notaro, and his grandparents tell him he should meet David Letterman. If anyone has seen David, please relay this information to him. Thank you. 

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

more less
Buy Tickets
Thu, Mar 16, 2023
8:30 PM
Fri, Mar 17, 2023
8:30 PM
Sat, Mar 18, 2023
8:30 PM
hide
March 23 - March 25

Kevin Bozeman

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 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

more less
Buy Tickets
Thu, Mar 23, 2023
8:30 PM
Fri, Mar 24, 2023
8:30 PM
Sat, Mar 25, 2023
8:30 PM
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April 13 - April 15

Rob Little

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

Watch Rob in action, and you’ll agree that he is one of the very best stand-up comedians in the country.  A sketch comedy player on the Fox Sports Net Show, "The Best Damn Sports Show Period" and "Last Call with Carson Daly," Little uses his training from the world famous Second City Comedy Club to create routines that are inventive, funny, spontaneous, and completely unique. He headlines clubs and colleges all over the country, has appeared in national television commercials and on such shows as Comedy Central's “Distraction,” Fox News and SiTV's “Latino Laugh Festival.”  He also earned a role on the CBS network summer hit series, “Fire me Please.”   Rob’s recently released 3rd comedy DVD/CD, is another testament to his talent and status as a comedic force.

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

more less
Buy Tickets
Thu, Apr 13, 2023
8:30 PM
Fri, Apr 14, 2023
8:30 PM
Sat, Apr 15, 2023
8:30 PM
hide
May 17 - May 20

Steve Gillespie

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

Steve Gillespie’s second comedy album “Alive on State” reached #1 on iTunes Comedy Charts and hit the top 10 on the Billboard charts. His 3rd comedy album “Liminal Bliss” was released earlier this year with Helium Comedy Records. It reached #2 on the iTunes Comedy Charts, so he is getting worse.

Gillespie has appeared on CONAN, Amazon Prime’s “Inside Joke”, and FOX’s “Laughs - All Stars”. Gillespie’s act a is a slaphappy balance of aggression and absurdity, coupled with a delightfully pushy persona that has earned him spots at some of the best festivals in country including the Bridgetown Comedy Festival, Boston Comedy Festival, 10k Laughs, and High Plains Comedy Festival in Denver, CO. He was named a finalist in CMT’s Next Big Comic, runner up for Best of the Midwest at Gilda’s Laughfest, and his debut album “Steve Fever” was named a top 10 comedy album of the year by ComedyReviews.com

Please note:

If you are purchasing Booth Seats, 1 Booth = 2 tickets for 2 people. Please do not purchase (2) Booths if you are coming with 2 people. We cannot refund erroneous additional booth purchases the night of the show.

Due to the adult content, themes, and language of our shows, we have an age requirement of 16 years old.

Showtime at 8:30 PM. Doors at 7:30 PM.

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

We ask that you please keep all conversations to a minimum during the show. It's a small room, and even whispering can be heard by the performers and people around you. If this seems like a no-brainer, it's because you are sober. After a drink or two, it sometimes seems less obvious!

more less
Buy Tickets
Wed, May 17, 2023
8:30 PM
Thu, May 18, 2023
8:30 PM
Fri, May 19, 2023
8:30 PM
Sat, May 20, 2023
8:30 PM
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(305) 985-7370

Comedy Key West

218 Whitehead St. Unit 5

Key West FL 33040

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