About The Show

City Winery Boston presents Puddles Pity Party live in concert on Thursday, November 16th at 8PM.

Puddles Pity Party, the 7-foot sad clown whose golden voice is comparable to rock legends like Tom Jones and Freddie Mercury, has amassed nearly 900K YouTube subscribers and performed sold out shows all over the globe including The Kennedy Center in D.C., San Francisco’s Palace of Fine Arts, London’s Soho Theatre and a residency at Caesars Palace in Las Vegas. You may recognize him as a finalist on Season 12 of America’s Got Talent and on the 2020 season of AGT The Champions, as well as his viral video collaborations with Postmodern Jukebox. Deftly combining melancholia with the absurd, Puddles has received endorsements and accolades from musical comedy legends like Eric Idle, Jack Black, Paul Reubens, Michael McKean, Drew Carey and Weird Al Yankovic.

Puddles had an action-packed 2022, with a guest appearance on the season four finale of ABC’s The Conners and performing a duet with the iconic Eric Idle on “Homeward Bound: A GRAMMY Salute to the Songs of Paul Simon” filmed for CBS. He even landed the coveted John Lewis Holiday advert in the UK with a cover of “All the Small Things”. He also embarked on three different tours, one with Piff the Magic Dragon, one with Tenacious D and one featuring Dave Hill which included a very special guest appearance by Leslie Jordan in his last live on-stage performance. Puddles also enjoyed touring the Mediterranean for four weeks as a feature performer on Virgin Voyages cruise line. That’s a lot of Frequent Cryer Miles!