December 01 - December 03

Ben Bailey

Ben Bailey

Long before he got behind the wheel of The Cash Cab -Ben Bailey left his home in a small town in New Jersey and headed to Los Angeles to pursue his dream of a career in show business... 6 weeks later he found himself onstage at The Comedy Store on the Sunset Strip! He got a laugh with the first thing he said and knew right away that he had found his calling... Shortly thereafter Bailey returned to the East Coast and started hanging out at the comedy clubs in New York City. He quickly became a crowd favorite. He has since performed at all the major festivals including Montreal and Chicago (Just For Laughs), the (hallowed &former) Aspen Comedy Arts Festival, The Edinborough Fringe Festival, and at clubs and Theaters around the world.

He has starred in 2 specials for Comedy Central, his most recent- "Road Rage and Accidental Ornithology has been a huge hit on Netflix for the last few years. By the summer of 2005, Bailey had appeared in Several Commercials, on FOX's "Mad TV" become a regular on "Tough Crowd w/Colin Quinn" recorded his 1st special for Comedy Central, and made stand-up appearances on HBO, NBC, "Star Search" "Last Call w/Carson Daly" and "The Late Show."

It seemed that Bailey's star was on the rise... and then along came "Cash Cab." Ben drove the Smash Hit series (New Episodes will air in April on Bravo and it's still on in syndication around the world) for over 550 episodes, and 6 Daytime Emmy Awards, Bailey has appeared on "The Tonight Show", "The Today Show", "The Oprah Winfrey Show", "Rachel Ray" and virtually every major morning show (TV&radio) in the country... He has gone on to host several other TV shows including "Who's Still Standing" for NBC, "Best in The Business" and "After the Catch" for Discovery as well as several Pilots...

He has appeared in numerous other TV shows - "30 Rock" "Parenthood" "Law and Order", "Hope & Faith", "The Knights of Prosperity", "One Life to Live"... as well as several films- "Bad Parents", "Don't Shoot the Pharmacist", "Bad Meat"... Bailey can currently be seen hosting segments on NatGeo's "Brain Games" and has a new show in the works with A&E as well as commercial campaigns for DTE Energy, Nature Valley nut bars, and Aldi Supermarkets.

12/01/2023 6:00 PM

Door Time: 5:00 PM

Other Showtimes

Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Ben Bailey 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!

Long before he got behind the wheel of The Cash Cab -Ben Bailey left his home in a small town in New Jersey and headed to Los Angeles to pursue his dream of a career in show business... 6 weeks later he found himself onstage at The Comedy Store on the Sunset Strip! He got a laugh with the first thing he said and knew right away that he had found his calling... Shortly thereafter Bailey returned to the East Coast and started hanging out at the comedy clubs in New York City. He quickly became a crowd favorite. He has since performed at all the major festivals including Montreal and Chicago (Just For Laughs), the (hallowed &former) Aspen Comedy Arts Festival, The Edinborough Fringe Festival, and at clubs and Theaters around the world.

He has starred in 2 specials for Comedy Central, his most recent- "Road Rage and Accidental Ornithology has been a huge hit on Netflix for the last few years. By the summer of 2005, Bailey had appeared in Several Commercials, on FOX's "Mad TV" become a regular on "Tough Crowd w/Colin Quinn" recorded his 1st special for Comedy Central, and made stand-up appearances on HBO, NBC, "Star Search" "Last Call w/Carson Daly" and "The Late Show."

It seemed that Bailey's star was on the rise... and then along came "Cash Cab." Ben drove the Smash Hit series (New Episodes will air in April on Bravo and it's still on in syndication around the world) for over 550 episodes, and 6 Daytime Emmy Awards, Bailey has appeared on "The Tonight Show", "The Today Show", "The Oprah Winfrey Show", "Rachel Ray" and virtually every major morning show (TV&radio) in the country... He has gone on to host several other TV shows including "Who's Still Standing" for NBC, "Best in The Business" and "After the Catch" for Discovery as well as several Pilots...

He has appeared in numerous other TV shows - "30 Rock" "Parenthood" "Law and Order", "Hope & Faith", "The Knights of Prosperity", "One Life to Live"... as well as several films- "Bad Parents", "Don't Shoot the Pharmacist", "Bad Meat"... Bailey can currently be seen hosting segments on NatGeo's "Brain Games" and has a new show in the works with A&E as well as commercial campaigns for DTE Energy, Nature Valley nut bars, and Aldi Supermarkets.