Flying Lessons

By Donald Rupe and Cesar De La Rosa; Directed by Donald Rupe
Produced by Osceola Arts
Part of the New York Musical Festival

Off Off Broadway, Musical
Runs through 7.28.19
Signature Theatre Center, 480 West 42nd Street


by Dan Rubins on 8.5.19


Flying LessonsMegan Valle, Esmeralda Nazario, and Brandon Martin (L-R) in Flying Lessons. Photo by Hector Sanchez, Jr..


BOTTOM LINE: Flying Lessons, a well-meaning new musical about a girl, her homework assignment, and her two friends Amelia Earhart and Frederick Douglass, doesn't quite take off.

History has its eyes on you at Flying Lessons, the New York Musical Festival entry all about what makes a hero. An assignment to write an essay about an inspiring historical figure flusters Isabella (Esmeralda Nazario). Her mom (Desiree Montes) works all the time, leaving frustrated Isabella to take care of things at home: how can she decide who inspires her when she doesn’t have time to figure out who she wants to be?

In fly figments of Isabella’s imagination—Amelia Earhart (Megan Valle) and Frederick Douglass (Brandon Martin)—to tell their stories and make the case that they should be her hero of choice. Collecting “ingredients for greatness” as she learns about the pair (Knowledge! Courage! Individuality!), Isabella quickly decides she’ll just write about both of them, although it’s clear from the beginning that she’ll come to find her most powerful inspiration a little closer to home. 

Donald Rupe (book, music, and lyrics) and Cesar De La Rosa (additional music) clearly aim to emulate Lin-Manuel Miranda’s hip-hop-fueled momentum, but, while the tunes are catchy, the generic lyrics usually miss the mark. The opening number, in which characters sing ad infinitum that they “gotta get up and go” is more reminiscent of Rebecca Black’s “Friday” in its textual depth. And while Hamilton’s off-rhymes are crafted and deliberate, those in Flying Lessons—apple and tackle?—are just clunky. 

But for his lively staging, Rupe, also the director, has gathered a cast that shows off the strong vocal arrangements. Nazario and Montes bring the heat in an early duet as mother and daughter battle it out. There’s some thrilling singing from Briana Moten as the history teacher who gets to lead a rap number and a gospel number, both of which are only necessary for showcasing her skills. Best of all, as a delightfully ditzy firework of a best friend, there’s Michelle Coben, delivering a passionate report on the cultural significance of Kim Kardashian and Chenoweth-ing her way through “More Like Me,” a jovial rip-off of “Popular.” 

If Flying Lessons doesn’t have the artistic wingspan for a commercial life, it’s easy to imagine a future for it on the educational touring circuit with some tweaks to the treatment of the historical heroes whose stories weave throughout the show. That said, the Earhart and Douglass sequences would be more engaging if Isabella actually had to choose between them. More significantly, the creators also haven’t quite figured out how to integrate the seriousness or significance of Douglass’ slavery narrative into a fairly peppy show: “We all have problems,” Douglass sings, a typical example of the show’s attempts to squish a lot of specific suffering into generalities. 

Flying Lessons doesn’t soar until its final moments, in which Isabella and her mother are movingly reconciled. But that sweet closing scene shows that the “ingredients for greatness” for making a musical—like real warmth and characters you care about—are somewhere in the mix.

(Flying Lessons is part of the New York Musical Festival and plays at the Signature Theatre Center, 480 West 42nd Street, July 22 through July 28, 2019. The running time is 90 minutes, no intermission. Performances are 7/22 at 8, 7/25 at 1, 7/27 at 1 and 5, and 7/28 at 5. Tickets are $35 and are available at or by calling 212-664-0979.)

Flying Lessons is by Donald Rupe (book, music, and lyrics). Additional Music by Cesar De La Rosa. Directed by Donald Rupe. Choreography by Kathleen Wessel. Set Design by Sarah Allen. Lighting Design by Jake Teixeira. Costume Design by Christine Hicks and Adam Prosper Ledo. Music Director is Jason M. Bailey. Orchestrations aby Jason M. Bailey, Cesar De La Rosa, and Josh Ceballos. Stage Manager is Katie Rinaldi.

The cast is Michelle Coben, David Lowe, Brandon Martin, Desiree Montes, Briana Moten, Esmeralda Nazario, Erick Perafan, Deanna Quintero, and Megan Valle.