Jackie Flynn

Jackie Flynn is an actor and comedian with prominent standup appearances, as well as extensive film credits to his name. Jackie has emerged as one of the funniest and most talked about comedians to come out of Boston, joining the ranks of Steven Wright, Denis Leary, Lenny Clarke, and Jay Leno, and gracing the stages of the IMPROV, COMEDY STORE, FLAPPERS, LAUGH FACTORY, and other noteworthy venues. He has parlayed his success as a stand-up to firmly establish himself in the film and television arena, featuring in several episodes of the hit series “The King of Queens,” and recent guest appearances on “Veep” on HBO and the Disney Channel’s “Bizaardvark.” He is also recognized for his role alongside the likes of Burt Reynolds, NFL Coach Jimmy Johnson, and Jerome Bettis as one of the "Men Of The Square Table" in the hugely popular Miller Lite "Man Law" commercials. Jackie is currently seen in the series regular role of “Tony” in “Loudermilk” (DirectTV Audience Channel), which is Peter Farrelly’s directing foray into television.

He is also one of the proud winners of the prestigious San Francisco Comedy Competition, as well as a featured performer at the Montreal Just For Laughs Festival gala. He was chosen to perform at the U.S. Comedy Arts Festival in Aspen, Colorado produced by HBO.

Early on in his career, Jackie was discovered on stage in Boston by the Farrelly brothers, who have since cast him in back to back roles in “King Pin”, “There’s Something About Mary”, “Me, Myself And Irene” “Shallow Hal” and “Stuck On You.” Recently, Jackie has had prominent roles in “The Three Stooges,” playing opposite Kevin James in “Here Comes The Boom,” and in 2017's film “Special Unit.”

Jackie’s golf background, popularity from a national Phil Mickelson commercial, and relationships on the PGA and celebrity golf circuit make him an often requested headlining comedian for affiliated and corporate event entertainment including Bay Hill in Orlando FL, Bel-Air Country Club in Los Angeles CA, The Hideaway Golf Club in Palm Springs, CA, Trump Doral in Miami FL. Morgan Stanley, Hertz, IBM, Intel, and Yahoo to name a few. 

Jackie is truly a "comic's comic" whose refreshingly unique brand of sarcastic observational humor puts him in a class all his own, apart from the many derivative cookie-cutter comics plying the airways today. Audiences young and old appreciate his wit and rapid-fire "take no prisoners" delivery.

Kevin Flynn

Kevin Flynn has thrilled audiences for years with his stand-up comedy performances having headlined at clubs and colleges across the country. Flynn’s career as a comedian took off after winning the Boston Comedy Riot in 1988, where he then began appearing on numerous comedy specials. He has since added several film and television credits to his name appearing in The Heartbreak Kid with Ben Stiller; Me, Myself and Irene with Jim Carrey; Osmosis Jones with Billy Murray, and Sex and the City.

After graduating from the University of Massachusetts where he was captain of the soccer team, Kevin went on to play three years of professional soccer in the Major Indoor Soccer League (MISL). Following his soccer career, Kevin transitioned from pro-athlete to professional sportscaster, host and entertainer. He covered World Cup Soccer for Fox Sports, ESPN and ABC. Flynn’s Sports Figure’s show on ESPN received the POLK Award for excellence in children’s programming.

In 1996, Kevin became the host of The Discovery Channel’s Go For It, an extreme outdoor adventure show where he swam with sharks, jumped out of airplanes and scaled dangerous peaks. The show led Kevin to create his one-man show Around the Kitchen Table, which won the “Best of Fest” at the Boston Comedy Festival and HBO’s prestigious U.S. Comedy Arts Festival in Aspen.

Along with continually performing his stand-up, Kevin is also the co-founder and executive director of the Nantucket Comedy Festival and is producing a FIFA World Cup soccer movie for Imax titled One World One Ball. Flynn has been a regular guest on FOX News, The Strategy Room and hosts Plum TV’s Plum Daily Show on Nantucket during the summer.

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