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Winter Park / Maitland Observer Thursday, Aug. 2, 2018 2 years ago

Winter Park Playhouse's Chris Leavy celebrates over a decade as musical director

Chris Leavy has helped run the show for over a decade.
by: Harry Sayer Black Tie Reporter

Winter Park Playhouse any given day, you might find music director Chris Leavy doing a number of things. He might be teaching music to the theatre’s performing cast. He might be hosting auditions for new band players or cabaret singers. He might even be putting the score together for a world-premiere musical with his husband. 

One thing you won’t catch him doing, however, is complaining about any of his many tasks — he’s having too much of a good time,

“It’s not work,” he said “Every once in a while, I’m like, ‘Suckers, you’re giving me money to do this?’ It’s a joy, and this particular theater is a joy. I’ve worked here longer than anywhere I’ve worked in my life. … It never feels like too much.”

Path to the Playhouse

Leavy has been the theater’s music director for nearly 12 years and never really expected to find himself in that position. While performing in Branson, Missouri, he eventually found himself tired of the ever-prevalent country music in the region. 

“I got to my midlife crisis,” Leavy said. “I said, ‘You know, some guys get a car, some guys get an 18-year-old, but I wanted a master’s degree.’”

Leavy spent three years taking as many classes he could — he couldn’t get enough of school — and eventually visited friends in Winter Park, where he booked a few piano gigs. Those same friends introduced Leavy to Roy Alan and Heather Alexander, artistic director and executive director for the playhouse, who asked him to do music direction for a show. Soon, Leavy became the official music director for the company. He rented an apartment on Aragon Avenue, right next to the playhouse, soon after. 

Leavy comes from a musical family — his dad sang in a barbershop quartet and his mother played accordion — and considers himself an “old soul” when it comes to his taste in music. He chalks up much of his taste to his 

parents, who were born in the 1920s, had him when they were in their mid-30s. While other children’s parents were listening to Elvis and Chuck Berry, Leavy’s folks kept it decidedly old-school with swing-era and opera tunes. 

He says his husband, who writes commercial jingles among other things, can play more than 30 instruments, but Leavy’s heart has always belonged to the piano. 

“My favorite thing of all is when you have a great performance and a good house and there’s just all that energy in that room,” he said. “The relationship in that room when you know the cast is nailing it and the audience is loving it. It’s a drug; it releases all those endorphins.”

Sing-along Cabaret

There’s a firm rule at the Winter Park Playhouse. No matter what song is playing, no matter how much fun you’re having, don’t sing and interrupt a cabaret performance.

But occasionally, Leavy likes to make an exception. 

“Every once in a while, I’ll be playing before the show, and I’ll be playing background music, and people will come up and just want to stand there and sing along,” he said. “And I just love it when people sing along, so I said, ‘I’m going to do a sing-along!’”

Leavy, along with singer Tay Anderson, recently performed the “As Time Goes On” sing-along cabaret June 20 and 21. The duo played some swing-era tunes and an Andrew Sisters medley that the audience sang along to with lyric sheets. He had a specific mental image when putting the piece together, as well.

“I thought of old wartime canteens and this vision of an old guy playing ‘Til We Meet Again’ on the piano and all the soldiers playing and all the young girls who came in to find a husband before they’d go off and get killed,” he said. “I’m doing an Andrew Sisters medley and a lot of swing-era stuff.”

It was one of the last cabaret for a short while. Leavy and the rest of the playhouse are gearing up for their new season of shows. Leavy and Ned have spent the summer putting together the score for the “Gigolo: The New Cole Porter Revue” musical in July. 

Moving Forward 

Leavy has seen the playhouse change in more ways than one in his time as music director. He just hopes he will see more change soon. 

“It’s a small theater, and in any business, the people make it but we are such a family here,” he said. “I can’t think of any business where people have been so in-tune and focused with the same goal and are on the same wavelength. We’re so supportive of each other. … It very quickly became a family.”


Harry Sayer is the Black Tie Reporter for the Observer. He is a graduate of the University of Central Florida and previously worked the Black Tie beat for the Observer newspaper in Winter Park and Maitland. You can catch him at one of Sarasota's fundraisers and shindigs. 


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