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INTERVIEW: Take some ‘Flying Lessons’ at NYMF

Photo: From left, Khristy Chamberlain (Amelia Earhart), Shonn McCloud (Frederick Douglass) and Esmeralda Nazario (Isabella) star in Flying Lessons. Photo courtesy of JD Casto / Provided by press rep with permission.


The historical figures Frederick Douglass and Amelia Earhart are at the center of a new musical set to premiere at the New York Musical Festival. Flying Lessons, with a book, music and lyrics by Donald Rupe, will play July 22-28 at The Alice Griffin Jewel Box Theatre at The Pershing Square Signature Center in New York City.

In the show, which is considered family-friendly entertainment, Isabella, a young Latina girl, is assigned a school project about a historical figure. Trying to decide which figure to choose, she is visited in her dreams by Earhart and Douglass.

Rupe not only created the musical, he also serves as its director. In his other life, he is the director of theatre at Central Florida Community Arts, helping to produce plays in a blackbox theatre in Downtown Orlando.

Recently Hollywood Soapbox exchanged emails with Rupe about Flying Lessons. Questions and answers have been slightly edited for style.

What inspired you to create this musical?

Well, there’s a few answers for that. One is that I received a grant to bring a theatrical production to all of the eighth grade students in my hometown of Osceola County, Florida. They wanted something that fit with their curriculum there. I looked at the ‘typical’ productions that I may direct, and I just didn’t find anything that worked. So I decided to write something myself.

So Frederick Douglass and Amelia Earhart hit some of the history curriculum. Then, as I started writing, of course I became really intrigued by my main character, Isabella. I actually taught in this school district for a long time (and I was a student there!), and I realized that I knew this girl — I went to school with her, I taught her, and in many ways parts of myself lived within her. So I became equally inspired to tell this girl’s story in front of an audience of 4,000 teenagers who don’t often get to see themselves represented in that way.

Was it difficult to get in the mind of a central character who is a teenage girl? How do you bring authenticity to the role?

You know, it wasn’t very difficult. When I write, I try hard to write about wonderful female characters just as often (if not mors) then I write about men. But aside from naming the character, I don’t put much thought into gender after that. I think young people probably share more than they realize, and that’s one of the things I tried to convey in this show. The things that Isabella is facing are also things her friends are going through, and her role models (real and imaginary) also went through themselves.

What do you believe are the important lessons of the show?

Throughout the show, Isabella is trying to figure out what it is about certain people that make them aspire to ‘greatness.’ Throughout the show she creates her own recipe for greatness. The most important lesson being, of course, that we each have those ingredients for greatness — and it’s in finding the courage to access those ingredients and really be the best version of yourself that leads people to success (in all its various forms).

What’s it like to direct your own musical? Was it always your intention to wear several hats?

To be honest, I wasn’t sure I wanted to direct this as well as write. I’ve not yet had the experience of working with a director on a piece that I’ve written. Because I’ve spent so many years as a director myself, it just kind of makes sense for me to stage the show, too. I also write like a director in that I think a lot about what the audience is experiencing and seeing from a director’s perspective.

So by the time the rehearsals begin, I’ve thought a lot about what I want the show to look, feel and sound like. So the control freak in me tells me to just direct it myself, I guess. As for wearing several hats — that’s a habit I hope to break one day.

Do you hope for a longer life after this New York City engagement? What does the future hold?

I’ve only been writing for five years or so, and every time I’ve written a show it’s been for a specific project. In this case, I wrote it for the eighth grade students in Osceola County, and when I was writing, that was all I intended. But then, and I feel like this happens to me every time, as I watched the show and saw the response I got from thousands of 13-14-year-olds, I realized that this show has a heart and a soul that matters, and it’s a story worth telling as many times as I can. So I applied for this festival, and now, of course, I have starry-eyed dreams for what is possible for the show. I’d like it to be seen as many times as it can be seen, wherever there are people who connect with it. 

By John Soltes / Publisher / John@HollywoodSoapbox.com

Flying Lessons plays July 22-28 at the New York Musical Festival. Performances take place at The Alice Griffin Jewel Box Theatre at The Pershing Square Signature Center in New York City. Click here for more information and tickets.

John Soltes

John Soltes is an award-winning journalist. His writing has appeared in The New York Times, Earth Island Journal, The Hollywood Reporter, New Jersey Monthly and at Time.com, among other publications. E-mail him at john@hollywoodsoapbox.com

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