Kevin Kelly brings his solo cabaret to the Winter Park Playhouse

Kevin Kelly. (Photo courtesy Winter Park Playhouse)

“I’ve Heard That Song Before,” a solo cabaret from local crooner Kevin Kelly is set to take place at the Winter Park Playhouse March 26-27. Playhouse Music Director Christopher Leavy will accompany on piano. The vocalist promises an evening filled with his thoughtful renditions of standards from the likes of Tony Bennett, Duke Ellington, Frank Loesser, Johnny Mercer, Bobby Darin and Dean Martin.

The singer has been performing professionally for the past 25 years across the country in theatre and cabaret shows. In addition to his solo performances, Kelly can be found warbling standards to Central Floridians in his jazz trio Kevin Kelly & the Mood Swings. The musician also teaches singing lessons and coaching at his very own Kevin Kelly Vocal Studio in the Orlando area.

“As a kid I was always drawn to the recording artists of the ’40s, ’50s and ’60s; Frank Sinatra, Tony Bennett, Ella Fitzgerald,” says Kelly. “They really shaped my childhood so I developed a way of imitating their sound, and through years and years of refining, created my own crooning style.”

Kelly noted that the jazz vocalists of that time firmly cemented a sense of storytelling through music and connection to the audience in his own crooning style early on. The aforementioned artists are a constant source of inspiration as Kelly performs songs audiences have heard him sing time and time again, as well as new interpretations for his upcoming cabaret.

“I think what drew me to that golden age of crooners was their way to tell a story, the honesty they had in their performance,” Kelly says. “If you go back and watch video recordings of Sinatra or Torme or Fitzgerald, they just had a different way of holding themselves- they were real, they were in the moment.”

When Kelly is not performing on stage in a theater production or cabaret, you’ll likely catch him at his studio working with vocal clients. His experiences working with his students has also influenced the way that he approaches production of a cabaret. He gave insight into how his experiences as a mentor have aided him in his journey to developing his own style.

“When I’m teaching vocal coaching with my clients, everybody is a unique puzzle and my favorite thing is to figure them out and see how they create their sound, it’s cliche but I do learn from my students just as much as they learn from me,” says Kelly. “As an artist we get to cherry pick from all those who have come before us, whether it be the crooners or jazz or pop, we get to choose all the things we like best and create our own unique sound.”

“I’ve Heard That Song Before” will be Kelly’s 13th solo cabaret with the Winter Park Playhouse, although Kelly recognizes the experience of putting on a cabaret can be remarkably different from traditional theatre.

“I’m not just performing, I’m singing and joking around with my friends which is what drew me to becoming a cabaret artist,” he says. “I was terrified the first time I did it because I was so used to being stuck behind a character as an actor, when you’re doing a cabaret it’s just you- you and the music, it scared me at first but now I think it’s my favorite way of entertaining.”

Kelly was most recently seen on the Playhouse mainstage in the theater’s production of “Ruthless! The Musical” in Fall 2023. His distinct vocals are reminiscent of prominent jazz and crooning legends, as illustrated in his numerous Sinatra-style cabarets and musical performances at the Playhouse such as “Murder For Two,” “Christmas My Way,” “The Rat Pack Lounge” and “Forever Plaid.” Kelly was also a featured soloist with the Orlando Philharmonic Orchestra in 2017 for his “White Christmas” special.

General Admission tickets are $20 plus a pre-purchased drink from the bar. Seating is limited so advance reservations are strongly recommended. Doors open at 6:30 p.m. for general seating for the 7:30 p.m. show. Tickets sell out quickly so call The Winter Park Playhouse box office for tickets at 407-645-0145 or purchase online at winterparkplayhouse.org.

The live cabaret will be filmed and available to enjoy virtually starting April 11 and be available through April 14. A private link will be sent at 5:00 p.m. April 11 and will be valid for 3 days. Virtual tickets are $20 and can be purchased online or by calling the box office.

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