Comedy Key West

10/05/2026

This Week at Comedy Key West!
Tom Dustin
October 8th - 10th 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

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...

10/05/2026

Tonight at Comedy Key West!

10/03/2026

Last chance to catch headliner Dan Boulger and host Steven Crane tonight! (Saturday, October 3rd). Dan Boulger is gearing up to record his special next week….don’t miss him live at Comedy Key West!
Doors: 7PM Show: 8PM

10/01/2026

Our website is currently experiencing technical difficulties. Tickets for tonight's show are available at the door. Please email us if you'd like to make reservations, as well.

09/27/2026

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!

09/19/2026

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

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....

09/16/2026

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.

09/14/2026

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

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...

09/09/2026

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

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...

08/31/2026

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

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...