Kevin Kelly New Cabaret

WINTER PARK — If you love cabarets, the Winter Park Playhouse musical theater, or just great singing, mark your calendar for Wednesday and Thursday this week to see Confessions Of A Crazed Crooner.

Popular singer and actor Kevin Kelly just finished a sold-out run of Murder For Two, the comedy musical performed at the Playhouse in August. Now Kelly is back, debuting his new solo cabaret as part of the Playhouse’s ongoing Spotlight Cabaret Series.

What is Kevin Kelly’s New Cabaret Show?

Confessions of a Crazed Crooner is being performed on Wednesday and Thursday at the theater located at 711 N. Orange Ave. in Winter Park. Kelly, well known for his expertise on the cabaret stage, will be accompanied by the Playhouse’s musical director Christopher Leavy on piano. 

Confessions of a Crazed Crooner offers audiences what the Playhouse bills as a “greatest hits” mix of musical theater selections and standards, showcasing his “easy-going style and smooth delivery of traditional classics with just the right blend of story-telling, conversation and humor,” the theater noted in a news release. “Audiences will be treated to the best loved tunes of Bobby Darin, Ray Charles, Stephen Sondheim, George Gershwin and of course Frank Sinatra, all delivered with the vocal elegance of a seasoned cabaret artist.”     

While Kelly has appeared in full productions at The Winter Park Playhouse over the past decade, he’s also known for his performances at plenty of other regional theaters, and has lent his talented voice to performances with The Orlando Philharmonic Orchestra and the Sarasota Symphony. Kelly also teaches students and professionals voice technique, audition strategy and piano.  

Heather Alexander, the Playhouse’s executive director, said this cabaret should be a great show, because  “Kevin is an outstanding performer and always puts on a fabulous cabaret! He will sell out fast so book your seats early!”

Where Can I See Kevin Kelly’s New Cabaret? 

General Admission tickets for Kevin Kelly’s new Cabaret are $20 with a one drink minimum. Performances will take place in the theater’s lobby. The lobby doors and bar open at 6:30 p.m. with the cabaret starting at 7:30 p.m. 

Seating is limited so advance reservations and early arrivals are highly recommended. To reserve a ticket, call the Playhouse box office at 407-645-0145 or purchase them online at

The live cabaret will be filmed and made available virtually from Sept. 30 through Oct. 3. A private link will be sent at 5 p.m. on Friday, Sept. 30. Virtual tickets are $20 and can be purchased online or by calling the box office.

Michael Freeman is an Orlando journalist, playwright, and author of the book “Bloody Rabbit”. Contact him at

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