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February 23 - February 25

Ross Bennett

Ross Bennett

“I dropped out of West Point to Become a Comedian...probably the greatest service I will ever do for my country” – Ross Bennett Ross Bennett left the United States Military Academy after deciding that he preferred to take aim and fire jokes instead of bullets. Since that day Ross’ comedy career has taken him from New York to Los Angeles and all points in between. Ross has developed a brand all his own described as “Comedy For The Rest Of Us” which resonates with everyday working class Americans who prefer clean humor that is both clever and politics-free. Ross discusses a wide variety of topics drawn from a life full of experiences ranging from his growing up with a father who was a Marine Colonel, to grade school snow days, to middle age medical procedures. Ross has been seen on over a dozen television shows including Comedy Central’s “Tough Crowd With Colin Quinn”, A & E’s “Evening At The Improv”, and “The Late Show with David Letterman”. In 2019 Dry Bar Comedy released Ross’ full length special “Comedy...For The Rest Of Us” which has been viewed millions of times.
02/24/2025 8:30 PM

Door Time: 7:30 PM

Other Showtimes

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

Please note:

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

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

Seating is first come, first served. Arrive early to maximize seating options.

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!

“I dropped out of West Point to Become a Comedian...probably the greatest service I will ever do for my country” – Ross Bennett Ross Bennett left the United States Military Academy after deciding that he preferred to take aim and fire jokes instead of bullets. Since that day Ross’ comedy career has taken him from New York to Los Angeles and all points in between. Ross has developed a brand all his own described as “Comedy For The Rest Of Us” which resonates with everyday working class Americans who prefer clean humor that is both clever and politics-free. Ross discusses a wide variety of topics drawn from a life full of experiences ranging from his growing up with a father who was a Marine Colonel, to grade school snow days, to middle age medical procedures. Ross has been seen on over a dozen television shows including Comedy Central’s “Tough Crowd With Colin Quinn”, A & E’s “Evening At The Improv”, and “The Late Show with David Letterman”. In 2019 Dry Bar Comedy released Ross’ full length special “Comedy...For The Rest Of Us” which has been viewed millions of times.