Come On, Get Happy

By Jay Boyar

Escapism is the message at the Winter Park Playhouse, which has  a musical mission and a family feel. And not surprisingly, people love it.

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Theater founders Roy Alan and Heather Alexander are old-school troupers.

Opening night at almost any theater can feel pretty cozy. The cast’s friends and family are in the house and good vibes fill the air. It’s the same at the Winter Park Playhouse, only more so. Much more so.

Just before November’s opening-night performance of Isn’t It Romantic?, co-founder Heather Alexander took the stage and spent a full 15 minutes greeting the sold-out house. She whipped up applause for audience members celebrating birthdays and raved about upcoming productions.

Then, throughout the show (a tribute to Rodgers and Hart), people clapped enthusiastically after, and sometimes during, the musical numbers. Some (unfortunately!) even hummed along with the cast.

“I love the family atmosphere,” says Rob Anderson, a director who has worked at several local theaters. “It’s very different from other places in town.”

That difference has been in the theater’s DNA ever since Heather and her husband, artistic director Roy Alan, opened the doors — or raised the curtain —  12 years ago. Since then, the venture has become so successful that it’s currently in the midst of a major expansion.

“We like to call ourselves the ‘Forget Your Troubles’ Theater,” muses Heather, noting that the Winter Park Playhouse is one of only two professional musical theaters in Florida. (Naples’ TheatreZone is the other.) “Just like in the Great Depression, musicals are a form of escapism. They take people on a journey.”


“I basically grew up in theater,” says Roy, who has a folksy yet debonair demeanor reminiscent of Fred Astaire. In fact, he played Astaire in Let’s Face the Music, a lively tribute show that he wrote and produced. “Started taking dance when I was 4. Did my first professional musical at the age of 8. Was offered my union card at the ripe old age of 9.”

That was in Houston, where Roy studied dance with the mother of his buddy, Patrick Swayze. And as he got older, he made it his business to learn everything he could about working in theater — both onstage and behind the scenes.

Two years after high school, Roy moved to New York, where he found work in various capacities on such 1980s Broadway hits as Pirates of Penzance, with Linda Rondstadt and Kevin Kline, and the original production of Nine, with Raul Julia.

But after 13 years in the Big Apple, he began looking elsewhere. And after putting up with one too many blizzards, he made the big move to Florida, where he was hired immediately at the Golden Apple, a dinner theater in Sarasota. There he spent three years directing, choreographing and performing in lead roles.

Then it was on to Jacksonville, where he performed in Singin’ in the Rain at the Alhambra Dinner Theater. Heather, as it happened, was also in the show, and sparks flew offstage. They didn’t play the lovers, but, a year later, they were married. Shortly thereafter, they decided to set up housekeeping in Winter Park, where they’ve remained.

“Mine’s a very different story,” offers Heather, the Ginger to Roy’s Fred. A vivacious blonde with large, avid eyes, she speaks rapidly — sometimes explosively.

“I started singing when I was 15, just singing in church and singing at school,” says Heather, who spent her teen years in Jacksonville. “My father wouldn’t allow me to get an arts-related college degree, so I ended up with a business management major, which has worked out very fine.”

She discovered theater in college at the University of Florida in Gainesville and the University of North Florida in Jacksonville, from which she ultimately graduated. Afterward, she auditioned for roles — and began getting them.

“When we came together in the marriage, we each had a child,” Heather notes, adding that they’ve since had two kids together. “Lots of our friends had moved down to the Orlando area because of all the [theater] work. Not only that, but the theme-park work was here. And it was an affordable place to raise a family.”

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In 2003, Alan and Alexander starred in the venue’s first major success, I Love You, You’re Perfect, Now Change, which they’d seen in New York. Response to the show made it clear that the formula for their success would be staging crowd-pleasing musical comedies.

The enterprise that morphed into the Winter Park Playhouse began 15 years ago as a school, the Master Class Academy, which the couple later sold. “We wanted to share our passion for the arts with the community and with children,” Heather says. As for the theater, she admits, it was a bit of an afterthought.

“We had this raw warehouse space in the back of the school,” Heather recalls, “and we wanted the community to see the [local] talent.” So the couple began mounting cabaret performances in the makeshift venue, which encompassed a small stage and 60 folding chairs.

Ray and Heather have from time to time performed in their own productions. But as the theater has grown increasingly successful, and their administrative duties have become more demanding, they’ve spent less time in the limelight.

Yet they did star this season in They’re Playing Our Song, prompting Orlando Sentinel reviewer Matt Palm to remark on their “charming chemistry.”

In most stage musicals, important changes tend to occur in sudden, dramatic ways. A character wins a big contest or meets the girl of his dreams or has a shocking realization. Although the rise of the Winter Park Playhouse was more like a series of baby steps, there was indeed at least one major leap.

On a trip to New York, the couple saw — and fell in love with — an Off-Broadway musical comedy called I Love You, You’re Perfect, Now Change. It’s about the urban dating scene (in the first half) and suburban married life (in the second).

“We thought: If we don’t do anything else, we’ve got to at least mount this show,” Heather reflects. “People back home would just think this is a riot.”

So in 2003 they presented a mini-season consisting of that show, the more familiar (and serious) Godspell and California Suite, a non-musical comedy.

The indisputable hit of that trio was I Love You. That success, plus some market research, told the couple that their audience preferred musical comedies. And it didn’t hurt that their biggest potential competitor, the musically oriented Mark Two Dinner Theater on Edgewater Drive, was in its final days.

“We realized what our restrictions were, our limitations in terms of what the public would support,” says Heather. “They did not want to see comedies. They wanted to see musical comedies.”

“That’s an interesting niche for a couple of reasons,” notes Elizabeth Maupin, who reviewed local theater for many years at the Sentinel. “One is that nobody else in town does musical comedy [exclusively], and especially no other professional company. The second is that there’s a certain segment of the theater-going audience that wants to laugh above all else.”


The facility’s facade leaves little doubt about the kind of theatrical fare it presents. “There’s lots of wonderful art that’s very dramatic; it makes you think,” says Heather. “For some people, that’s fine sometimes. But other times, they just want a nice, frivolous escape.”
The facility’s facade leaves little doubt about the kind of theatrical fare it presents. “There’s lots of wonderful art that’s very dramatic; it makes you think,” says Heather. “For some people, that’s fine sometimes. But other times, they just want a nice, frivolous escape.”

A stone’s throw from Park Avenue, the Winter Park Playhouse has been located at 711 Orange Ave., between U.S. 17-92 and Fairbanks Avenue since 2009. The outside isn’t much to look at: a flat facade featuring two signs that sport the theater’s name.

To one side of one sign, in bold block letters, is the word “MUSICAL,” and to the other side, in the same font, is the word “THEATRE,” leaving little room for doubt as to just what sort of shows are presented within.

The lobby, meanwhile, is a tastefully decorated space that looks rather like an old estate’s comfortable parlor, complete with a baby grand piano.

The current expansion, which was made possible when the school relocated, will increase the lobby to three times its size and add two additional restrooms. There’ll also be more space for offices and set storage as well as an additional dressing room. Up to now, male and female performers had been sharing space.

Fifty new seats will augment the existing 123 in the performance area. But that will have to wait for Phase II, projected to get underway next summer. The added capacity won’t come a moment too soon for Roy and Heather.

“We’re at a point where we have more demand than we’re able to meet,” says Heather, who boasts that the theater has more than 1,000 subscribers. That number is bolstered by significant group sales from retirement communities, a reflection of the nostalgic appeal many of the shows offer. “We sell out over 80 percent of our performances.”

And while Heather and Roy are proud to have their theater in Winter Park, they also see a downside.

“I think people do have the misconception that because we’re the Winter Park Playhouse that we get an unbelievable amount of community [financial] support, because it’s a wealthy city,” Heather explains. “We don’t get city support at all, currently, but we’re hoping that will change.”

The not-for-profit theater did, however, receive $40,000 in 2014 from Orange County, which was about enough to mount one show. United Arts kicks in a bit, too, and the couple is investigating additional grant opportunities.


After the opening-night performance of Isn’t It Romantic?, Heather reappeared, along with the cast, to hug each audience member on his or her way out.

“Heather hugs you, no matter who you are,” explains Anderson, the director, whose next show at the playhouse is January’s The Rat Pack Lounge. “You’re very much made to feel at home.”

And yet, as Maupin points out, “Not everybody loves light musical comedy.” In fact, musicals of any kind leave some folks scratching their heads: Why would two seemingly sane characters, who were chatting perfectly nicely just moments ago, suddenly take it into their heads to start singing at each other and dancing around the stage?

Heather and Roy are so busy dealing with the demands of their growing enterprise that they don’t fret much about questions like that.

“There’s lots of wonderful art that’s very dramatic; it makes you think,” says Heather. “For some people, that’s fine sometimes. But other times, they just want a nice, frivolous escape.”

That’s what’s waiting for them — and for you — on the stage of the Winter Park Playhouse.



The Winter Park Playhouse typically presents seven shows per season. So far this season, it has offered Backwards in Heels: The Ginger Rogers Musical; Neil Simon’s They’re Playing Our Song; Isn’t It Romantic? A Tribute to Rodgers & Hart; and Shout! The Mod Musical, featuring the music of Petula Clark, Dusty Springfield and Lulu. Yet to come this season are:

• The Rat Pack Lounge. Jan. 16-Feb. 14. It’s New Year’s Eve and the Rat Pack, now in heaven, discovers it has unfinished business back on earth. So Frank Sinatra, Dean Martin and Sammy Davis Jr. assume the terrestrial bodies of three barflies. Somewhere along the line, someone named Angie pops up. (Angie Dickinson?) The show’s more than 30 hit songs include “My Way,” “Volare,” “Everybody Loves Somebody Sometime” and “Bye Bye Blackbird.”

• A Day in Hollywood/A Night in the Ukraine. March 6-28. This Tony Award-winning show offers two one-act musicals loosely connected by a Tinseltown theme. The first half, a bit of a cavalcade, is set at Grauman’s Chinese Theatre in the 1930s. The second half is an invented Marx Brothers movie, vaguely based on Chekov’s The Bear, of all things. The songs are a mixture of classics (including “Over the Rainbow”) and originals. 

• Putting It Together. April 17-May 9. Set at a chic Manhattan cocktail party, this musical revue borrows almost 30 songs from Stephen Sondheim’s other shows. Those classics include “Sorry-Grateful” from Company, “Pretty Women” from Sweeney Todd and “Everybody Ought to Have a Maid” from A Funny Thing Happened on the Way to the Forum.

In addition, the playhouse presents two nights of cabaret each month. Call 407-645-0145 or visit for further information.

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