Comedy Key West

Dan Boulger Returns to Comedy Key West
September 30th - October 3rd
8PM

Dan Boulger started doing standup in late 2004. He won the Boston Comedy Festival in 2006. After that he appeared on Comedy Central, The BBC, and the HBO Aspen Comedy Festival. He has done shows on the Comedy Central live and College humor live tours.

Tickets are available now!

One of Key West's favorite comedian is coming back!
Landry is returning to Comedy Key West
September 23rd - 27th

Landry is best recognized for his likable hair, sprouting from charismatic follicles. He is a Canadian born in*******al 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.
Tickets available on our website at

Comedy Key West | Landry Landry is best recognized for his likable hair, sprouting from charismatic follicles. He is a Canadian born in*******al 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....

This week! Aaron Berg returns to Comedy Key West! Aaron Berg is a fixture on the NYC comedy scene, he is undeniably hilarious and packs the maximum amount of laughs per minute possible. No two sets are ever the same. Aaron was just cast in Uwe Boll’s new feature film The First Shift, which bolsters his acting resume to over 50 projects including cult classic feature films like Detroit Rock City, Boondock Saints 2, The Kitchen opposite Melissa McCarthy and Saturday Night Live’s The Ladies Man.

We love having Aaron perform at our club, and you will too! Shows Wednesday, September 16th-Saturday, September 19th.

This Week at Comedy Key West
Aaron Berg

September 16th - 19th at 8 PM

Aaron is a fixture on the NYC comedy scene, he is undeniably hilarious and packs the maximum amount of laughs per minute possible. No two sets are ever the same.

Aaron was just cast in Uwe Boll’s new feature film The First Shift, which bolsters his acting resume to well over 50 projects including cult classic feature films like The Boondock Saints 2, Detroit Rock City, The Kitchen opposite Melissa McCarthy
and Saturday Night Live’s The Ladies Man. He played the role of “Cork” opposite Joseph Gordon Levitt, Jeff Daniels and Isla Fisher in the Independent Spirit award winning film The Lookout. He was also a lead in the dark comedy series 24 Hour Rental now airing on Amazon.

Aaron’s world record breaking documentary about stand up comedy in NYC “25 Sets" is now available on Amazon. Aaron’s Comedy Central debut on THIS IS NOT HAPPENING has 2 million views and he has made two appearances on AXS TV’s LIVE AT GOTHAM as well as appearances on GOTHAM VR, BIG JAY OAKERSON’S “WYFD?!?” and Comedy Central’s Roast Battle Season 2 and DC comics’ feature film THE KITCHEN.

Tickets are available now on our website at

Comedy Key West | Aaron Berg Aaron Berg is a fixture on the NYC comedy scene, he is undeniably hilarious and packs the maximum amount of laughs per minute possible. No two sets are ever the same. Aaron was just cast in Uwe Boll’s new feature film The First Shift, which bolsters his acting resume to well over 50 projects inclu...

This Weekend at Comedy Key West
Tom Dustin
September 11th & 12th at 8 PM

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 (B**r! B**r! B**r!) 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.

Tickets are available on our website at

Comedy Key West | Tom Dustin 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 Ad...

September 3rd - 5th
Dave Landau

As appeared on Last Comic Standing, Comedy Central, Fox

Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening,” and he is a regular panelist on Fox shows such as “Fox Across America,” “Who Can Forget?,” and “Kennedy.” He was also a finalist on season 8 of “Last Comic Standing” on NBC.

Dave served as co-host on “The Artie Lange and Anthony Cumia Show,” “The Anthony Cumia Show with Dave Landau,” and was a writer and on-air personality on Louder with Crowder. He is currently the co-host (along with “Quarter Black” Garrett) on a late-night sketch series called “Normal World” on Blaze TV. He regularly performs at clubs and theaters throughout the country.

Tickets are available on our website at

Comedy Key West | Dave Landau Getting his start in Detroit at the Second City’s Conservatory, Dave Landau has become one of the most in-demand headliners working today. Dave’s laid-back demeanor and dark style of comedy landed him on Comedy Central’s “This is Not Happening,” and he is a regular panelist on Fox shows su...

Monday, Aug 31st | 12:30pm
A Pirate Looks Back: Jimmy Buffett Tribute

Looking for a lunch experience like no other? 🍔🎶🦜
Join us for Key West’s best all-inclusive dine-in musical experience, revisiting the glory days of 1970s Key West when a young songwriter named Jimmy called this island home.
Featured during Just A Few Friends Key West !

Acclaimed musician, actor, and Buffett historian Caleb Hogan appears in character as the man himself in a show blending live music, storytelling, humor, and of course...Cheeseburgers! Enjoy a journey back in time to a place where artists and misfits lived the eclectic Bohemian dream, and our favorite "grandson of a sailor" roamed the land.

Get Tickets Now!

Comedy Key West | A Pirate Looks Back: Jimmy Buffett Tribute Show A Must-See Lunchtime Tribute Show, live on stage in the heart of Key West![Reservations Recommended!]There are many places to eat lunch in Key West. In some spots, you can have lunch with live music. But there’s only ONE place to have lunch with a legend. Join us for Key West’s only all-inclusiv...

Tonight! Friday, September 28th Comedy Key West is having a free tasting! Black Market Delta-9 “High Tails” available at door time (7:00pm) and ends at showtime. (8:00pm) Come sip and taste, and feel free to stay for the show! Jenny Zigrino is headlining, she’s a killer! (Must purchase ticket to stay for the comedy).

BLACK MARKET

This week! New to our stage, we welcome Jenny Zigrino . Jenny combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty and undeniable charm create a compelling comedic experience you won’t forget.
She made her late night debut on Conan, with a total of three guest appearances. In 2023 she performed on the Late Late Show with James Cordon and was met with rave reviews. She was a Just For Laugh’s New Faces in 2016 and since then has been featured on Comedy Central, MTV, HBO, Netflix is a Joke and many others. We are so excited to have her! Tickets available now through our website.

Coming up this week at Comedy Key West
Comedian Jenny Zigrino
August 27th - 29th

With the sweetness of the midwest and the sharp edge of the east coast, Jenny Zigrino brings a powerful comedic performance to any stage. She combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty and undeniable charm create a compelling comedic experience you won’t forget.

She made her late night debut on Conan with Conan O’Brien and performed a total of three guest appearances. In 2023 she performed on The Late Late Show with James Corden and was met with rave reviews. She was a Just For Laugh’s New Faces in 2016 and since then has been featured on Comedy Central, MTV, HBO, Netflix is a Joke and many others. She starred in films such as Bad Santa 2 along Billy Bob Thornton and in the horror comedy Too Late in 2021. She’s headlined festivals like Moon Tower, New York Comedy Festival, and High Plains Comedy Festival. She’s written and performed several comedy specials including Comedy Central Presents the Half Hours and her latest hour special Jen-Z premiered on Comedy Central Digital in 2023. Her latest appearance on After Midnight with Taylor Tomlinson has been hailed as one of the funniest episodes yet by fans. Her most recent Don’t Tell Comedy special is out now.

Tickets are available on our website at

Comedy Key West | Jenny Zigrino With the sweetness of the midwest and the sharp edge of the east coast, Jenny Zigrino brings a powerful comedic performance to any stage. She combines hilarious anecdotes and sharp, witty observations with a cheeky style that challenges social norms and what it means to be human. Her brutal honesty....