Puddles Pity Party
When: September 28, 2025 8:00 PM
Where: Key West Theater, 512 Eaton St, Key West, FL 33040
Get ready, Key West—Puddles Pity Party is bringing his unforgettable blend of heartbreak and hilarity to the stage at the Key West Theater.
Standing seven feet tall and dressed in full clown regalia, Puddles Pity Party has captivated audiences worldwide with a voice often compared to icons like Tom Jones and Freddie Mercury. With over 900,000 YouTube subscribers and a track record of sold-out performances at iconic venues such as The Kennedy Center, London’s Soho Theatre, and Caesars Palace in Las Vegas, Puddles has proven himself a global sensation.
Recent career highlights include a show-stopping duet with Eric Idle on The Galaxy Song, a poignant performance in CBS’s Homeward Bound: A Grammy Salute to the Songs of Paul Simon, and a viral collaboration with Primus on Dio’s Holy Diver. Fans may also recognize his unmistakable vocals from the UK’s famed John Lewis Holiday advert, or from his appearances on America’s Got Talent, The Conners, and AGT: The Champions.
In 2025, Puddles is preparing to release a brand-new album while embarking on an ambitious tour with “Weird Al” Yankovic, spanning over 70 U.S. dates.
Praised as “Pagliacci by way of Pee-Wee Herman and David Lynch” (The Atlanta Journal-Constitution), Puddles blends operatic power with tender vulnerability. Critics and stars alike—from Simon Cowell and Jack Black to Eric Idle and Penn Jillette—have sung his praises, calling him everything from “fantastically brilliant” to “a perfect powerful avant-garde art piece.”
Don’t miss the chance to experience the clown with the golden voice live in Key West. Equal parts heartwarming, heartbreaking, and hysterically funny, Puddles Pity Party is a show you’ll never forget.
You might like these Events
Key West Triathlon
The Key West Triathlon returns on Sunday, December 14, 2025, offering athletes a unique race experience in one of the most vibrant destinations in the U.S. Hosted at Higgs Memorial Beach, 1000 Atlantic Blvd, Key West, FL, the event is designed as the ultimate “tri-cation,” blending competition with relaxation in a lively island setting. Brought to life by Integrity Multisport™ and proudly sponsore...
New Year's Eve: Conch Shell Drop at Sloppy Joe's
The arrival of 2026 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock. Inside Live music on stage noon-2:00...
Key West Literary Seminar
The 43rd annual Key West Literary Seminar returns January 8–11, 2026, bringing readers and writers together for four days of world-class literary programming at the historic San Carlos Institute. Each year the event explores a unique theme, and in 2026 the focus is “Pay Attention! The Novel, or The Long Form in a Time of Short Attention.” The Seminar features presentations, readings, and conversat...
