Kevin Kelly Credit: photo courtesy of the artist
Over the past quarter-century, Kevin Kelly has become one of Central Florida’s most celebrated crooners by effortlessly transporting audiences back to the era of Bing Crosby, Bobby Darin and Frank Sinatra. This week, on March 25 and 26, Kelly cranks up his musical time machine again with On the Atchison, Topeka and the Winter Park Stage, the latest in his long-running series of cabarets for Winter Park Playhouse and the final WPP show to premiere in their temporary home at Orlando Shakes before they return to their renovated Orange Avenue HQ.
The youngest of five children, with a minister for a father, Kelly began playing piano and singing in church at an early age. “Everybody played some kind of instrument at some point in their lives, so I think I got bit very young,” says Kelly. “I just liked being on stage.”
Even though he moved into secular music during college at Kansas State University, his family remains supportive and have unexpectedly showed up for his shows, from Bent to Grease. “My favorite moment is, when I did Pump Boys and Dinettes years ago, my father snuck in a little recorder, and he just held it in his coat and recorded the show because I was doing country music and he was a huge country music fan,” Kelly recalls. “So that little cassette sat behind his desk forever.”
After a post-college stint as music director of a small theater company in Newport, Rhode Island, Kelly came to Orlando in 1997 seeking escape from northern winters and lived on Kirkman Road [full disclosure: with my wife’s college roommate] while working full-time as a character coordinator and scheduler backstage at Walt Disney World.
“I’d stopped performing. There was actually about a 10-year period where I didn’t sing, didn’t play [music], I didn’t do anything,” he says. “It was soul-crushing. I said, ‘I’ve gotta do this, because it’s what I do.’”
After getting cast by Katrina Ploof for a reading at Shakes, Kelly was hired by Mad Cow’s Alan Bruun to play John Wilkes Booth in Sondheim’s Assassins, which coincided with him leaving Disney. Aside from an abortive outing as an Ollivanders wandkeeper when Universal’s first Harry Potter land opened — “This kind of nitpicky corporate theater really isn’t for me, so I walked out of that shift and I never went back,” he says — Kelly has largely worked under contract for Winter Park Playhouse, making him one of the relatively rare Actors Equity union members making a living in Orlando outside the theme parks.
“I held out for a long time only because companies would rather hire a non-Equity [performer] because it’s less expensive, so I feel like that actually did allow me to book a little more,” Kelly says. “But as I got older … I thought, I’m getting of a certain age, and I need to really start thinking about insurance and all that stuff. So that was the big impetus for me, and I’m happy to to be a part of the union.”
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Although he’s starred in many scripted shows for Winter Park Playhouse since first getting cast in Golf: The Musical over 15 years ago, he says cabaret is his favorite format for entertaining “because you’re free. You don’t have to be a character; you’re just you. I get to sing songs that I love — that I connect with — and tell stories [and] stupid jokes [that] make the audience groan. … Especially now we’ve got so much on our minds, weighing us down day by day with the news and social media and stuff, so I just really strive to keep everything fun and light.”
When asked how he develops his cabarets, Kelly confesses, “I always have good intentions, and I always think, ‘Oh, God, I’m going to do some kind of theme.’ [But] nine times out of 10, I get all my songs on little 3-by-5 cards [and] shuffle them around until I get the combination I like. And then I just kind of build it around the songs.” He says his latest show was scrapped and rewritten from scratch in just four weeks: “It may be kind of a mishmash of songs, it’s always kind of an organized chaos, but that’s what I enjoy.”
For this outing, Kelly is once again accompanied by keyboardist Chris Leavy, his frequent collaborator and a WPP fixture. “We’ve done so many of these shows together, we joke that I can send him a song list and I’ll see you the night of the show, because after working so much together we know how each other works. I can literally just turn and look at him and he’ll know that I have no freaking clue what song is coming next,” says Kelly. “He is one of the most beautiful minds in in this town, so talented, such a treasure trove of information.”
Winter Park Playhouse is scheduled to cut the ribbon for their newly rebuilt home on July 7, beginning their season in August on an expanded stage with additional breathing room behind the curtain, which should make quick changes more comfortable. But one thing that shouldn’t change is the feeling that has made WPP an anchor of the theater community.
“I’ve always found that Winter Park Playhouse is a very warm and very family-oriented kind of atmosphere,” says Kelly. “Meaning that when you start working for them, you become part of their family.”
Kevin Kelly, “On the Atchison, Topeka and the Winter Park Stage”: 7 p.m. Wednesday and Thursday, March 25-26; Mandell Theater, Lowndes Shakespeare Center, 812 E. Rollins St.; 407-645-0145; winterparkplayhouse.org; $23
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This article appears in March 25-31, 2026.
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