Comedy is art. And art is subject to opinion. Which makes it impossible to judge fairly. But we’re doing it anyway…

Florida comics bring their best bits to our stage, and the audience helps pick who should win the night and the cash!  Wednesday’s show will also feature an interactive first look at “The Key West Gameshow”, a fantastically fun night with your favorite game shows, coming soon to Comedy Key West.

Billy Anderson is a standup comedian who can be heard on Audible’s “Sounds Like America” hosted by Jackie Kashian and seen on season 3 of the syndicated program “Laughs” on Fox television. In 2018 he released his first live comedy special titled “America’s Sweetheart” through The Harmon Brother’s Dry Bar Comedy series on Amazon Prime. You can see Billy both at the Hollywood Improv and touring internationally as the host of the hit comedy showcase The Gateway Show.

The Gateway Show has a simple premise: Stand-up comedians take to the stage sober to tell their BEST jokes, then they go to an undisclosed location to get WAY too high, only to come back to the stage and ATTEMPT to tell more jokes while completely stoned.

Dan Soder is a New York City-based comedian who’s best known as ‘Mafee’ on the hit Showtime Billions series. His HBO Special “Son of a Gary” debuted December 7th, 2019. He has a Half Hour Special on Netflix’s “The Standups”. His first hour-long stand-up special, Not Special premiered in 2016 on Comedy Central.

A comedian known for his sharp wit, unique delivery, and brilliant affinity for cuss words, John Caparulo is a seasoned comic whose dry, no-nonsense Midwestern sensibility endears him to audience members of all kinds. He began his comedy career performing in clubs in Cleveland and Pittsburgh in the late ‘90s before coming to Hollywood to hone his skills on stage and work the door at the legendary Comedy Store. Caparulo's breakout performance at Montreal's Just for Laughs in 2003 led to spots on The Late Late Show with Craig Kilborn, The Tonight Show with Jay Leno, Jimmy Kimmel Live, and he appeared over 150 times as a panelist on Chelsea Handler’s popular E! show Chelsea Lately.

An evening of candid, comedic storytelling - followed by a live Q&A with the audience.

From life, to career, to scandal - it’s everything you want to know…and some things you may wish you didn’t. Whether you know her from television (SNL, VH1’s The Surreal Life, Host of OUTtv’s For the Love of DILFS), from magazines (Vogue, Vanity Fair, Rolling Stone), from the Peacock documentary Stormy, from movies (that can’t be mentioned here), or from the headlines - Stormy Daniels is now bringing her talents to the comedy stage. Stormy’s set is packed with hilarious stories from her time in adult entertainment, her personal life as a wife and mother… and of course, politics and scandal. Never one to shy away from the bold truth, every show ends with a live Q&A.

Bostonian Tom Dustin is the funniest guy you’ve probably never heard of. He was the only American to ever win the $25,000 Yuk Yuk's Great Canadian Laugh-off, (resulting in future contests being closed to American comics) USA! USA! USA!  He was also the winner of the Sam Adams Comedy Festival. Beer! Beer! Beer!  He's done Comedy Central, The Comedy Channel (Canada), local & national radio, podcasts, festivals, and roasts.

Wyatt Cote dropped out of college one year shy of graduation to pursue a career in comedy and has since become one of the top competitive comics in the country with five contest wins to his credit including the 2021 World Series of Comedy. He was the runner up in the 46th annual San Francisco Comedy Competition and now tours the country performing full time. His stand up has appeared on Laughs on Fox and ABC news.

Sean Patton is a comedian based in New York, by way of New Orleans. He began doing stand-up in the Crescent City and has since performed in comedy clubs and festivals across the world, including The Melbourne International Comedy Festival (2011, 2018), The Glasgow Comedy fest (2016), the Dublin Comedy fest (2017), and The Edinburgh Fringe (2017, 2019). Other festivals appearances include SXSW (2016, 2017, 2018, 2022), The Moontower comedy festival (2012, 2013, 2014, 2019), Just for Laughs Chicago (2013), Just for Laughs Toronto (2013) and Just for Laughs Montreal (2008, 2010, 2012, 2016, 2018).

From festivals to late-night television appearances, Eddie Gossling has been holding it down in the comedy industry for over 20 years. Known for his sharp wit and engaging stage presence, he has built a reputation and crafted a style that's equal parts edgy and endearing. Arguably his most notable accomplishment outside of stand up is his involvement with Comedy Central's "Tosh.0," where he served as a writer and co-executive producer for 12 seasons. Gossling's contributions to the show helped shape its comedic style and earned him recognition within the industry. In addition to his work behind the camera, Gossling has also made appearances on popular late-night shows like "Jimmy Kimmel Live" and starred in his own Comedy Central special.

Doug Benson is known for his popular podcasts (Doug Loves Movies and Getting Doug With High), his films (Super High Me, The Greatest Movie Ever Rolled, Chronic-Con: Episode 420), appearances on TV shows like @midnight, The Trailer Park Boys and You're The Worst, and for presiding over The High Court as ‘Judge Doug’ on Comedy Central.

In 1986 Tony V was named “Funniest Person in Massachusetts” by Showtime television. He followed this achievement with several performances on HBO, the Arts and Entertainment Network, Comedy Central and MTV. From 1987 through 1992 Tony V became the “spokesperson” for American Tourister Luggage. Remember the suit case smashing gorilla? It was Tony that gave the ape it’s distinct voice and temperament. Touring extensively in and out of his high tech forty-five thousand dollar yak hair gorilla suit, both Tony and his alter ego had many interesting adventures. If you get a chance ask Tony about a meeting between The Gorilla, Spuds MacKenzie and Ronald McDonald. You won’t believe your mind.

Amos Gill is one of Australia’s hottest comedians, now making waves internationally as a touring headliner across the USA, UK, and Australia. Known for his sharp humor and quick wit, Amos first gained attention as a beloved Adelaide radio host on Amos, Cat & Angus. After leaving radio in 2018, he quickly became a comic to watch, earning accolades such as runner-up in triple j’s RAW Comedy competition and hosting the Melbourne International Comedy Festival’s prestigious Comedy Zone.

Gastor Almonte is a Dominican-American stand-up comedian, writer, and podcaster based in New York City. Raised in Brooklyn, he’s known for his warm, thoughtful delivery and deeply personal storytelling—blending culture and identity into comedy that’s both smart and emotionally grounded. Gastor has been featured on Comedy Central and NBC, and he performs regularly at top clubs and theaters across the country. His work has also appeared at major comedy festivals and across digital platforms, where he’s earned a reputation as a comedian’s comedian—respected for his writing, honesty, and point of view.

For over 13 years, from the stage to the silver screen, Steve Rannazzisi has made audiences laugh. Currently, Rannazzisi stars and writes alongside Katie Aselton, Mark Duplass, Nick Kroll, Jonathan Lajoie, and Paul Scheer on the critically acclaimed FX Network comedy series, The League, which is produced by Jeff and Jackie Schaffer.

Jessimae Peluso is a stand-up comedian, writer, performer, TV and podcast host whose work blends raw comedy with emotional depth. Known for her breakout role on MTV’s Girl Code and hosting Netflix’s Tattoo Redo and Surviving Paradise, Jessimae has spent nearly two decades turning personal pain into punchlines.

Jimmy Dunn is a stand-up comedian and actor from Boston, who currently plays “Moose” on the Paramount+ reboot of the iconic sitcom FRASIER. ​He can be heard most Tuesdays on The Greg And The Morning Buzz radio network. He got his start in "show business" telling jokes in a bar in Gloucester, Massachusetts, where he was paid in beer and fried clams. Since then, he’s gone on to perform at some of the world’s most prestigious comedy events, including the Late Show with David Letterman, CONAN, Montreal’s International Just For Laughs Comedy Festival, and Denis Leary’s Comic’s Come Home in Boston. Jimmy’s first major television role was as Sean McCarthy on the ​CBS sitcom, THE MCCARTHYS. He’s also written on several television projects, including two episodes of LOUDERMILK that he co-wrote with Academy Award winner Peter Farrelly.​

Cory has a Dry Bar Comedy Special -"Bad Teacher" - that snagged over 80 million views. His debut album, "The Collage Dropout," was released by 800 Lb. Gorilla Records and charted at #2 on iTunes & Billboard (because it was the only album released that week). Cory was a finalist in the Seattle Comedy Competition which means he didn't win and was in Season 2 of Netflix's "Huge in France" with Gad Almelah.

Named “Best Comedian in Miami” by the Miami New Times, Dave Williamson tours heavily, both headlining his own shows and as the supporting act for Bert Kreischer. His second album, “Trying My Hardest” was just released by Stand Up! Records and reached #1 in the iTunes Charts for Comedy. Dave's material is in heavy rotation on many SiriusXM stations. Dave often talks about family, highlighting stories from his youth to navigating the role of Father & husband himself. He is obsessed with BBQ, and hosts his own podcast called “Meat Dave”.

This Florida native is one of America's hottest up and coming comedians. He can be seen each and every Sunday at 11pm hosting his own show, "Viral Breakdown" on the Afrotainment Channel on Dish Network. He has graced the stage with some of America’s top talent including, Joe Torry, Jimmy J.J Walker, Tom Rhodes and Michael Winslow. He was a finalist for NBC’s stand up for Diversity and appeared on the FOX comedy club. He was the 2011 and 2012 winner of the Orlando Improv’s “Clash of the Comics.” Now James spends his time touring clubs and casinos all over the country from Orlando to Las Vegas bringing the funny.

Caitlin Peluffo has been featured on the Late Show with Stephen Colbert, The Late Late Show with James Corden, After Midnight, 2022’s Just For Laughs Festival, and has hosted her weekly podcast, Good Time Gal with Caitlin Peluffo for over three years. She has also been featured on Comedy Central’s “Featuring” series, and has a Don’t Tell Comedy Set with over 150k views on YouTube. With Caitlin, no subject is off limits, however, she did make a promise to her mother that she would never, ever discuss that one time she took those ‘whorish, yet tastefully executed’ photos for a guy she used to bang in the military. She may be a patriot, but a promise is a promise.

Jackie Flynn is a seasoned Boston-bred comedian and actor who has transitioned from legendary stand-up stages like The Comedy Store to a prolific screen career. Beyond his "Man Law" commercial fame, Jackie has appeared in The King of Queens and Veep. He currently stars as "Tony" in the Peter Farrelly-directed series Loudermilk.

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.