Rebecca Gayheart, known for her role as Julie Freeman in the 1999 dark comedy Jawbreaker, is making a highly anticipated return to the film's universe with her debut musical theater performance in Jawbreaker The Musical. The production, penned by original Jawbreaker writer/director Darren Stein, sees Gayheart take on the role of Principal Sherwood, which ingeniously merges two characters from the cult classic: Carol Kane's mousy Ms. Sherwood and Pam Grier's tough Detective Vera Cruz.

Currently in rehearsals for the musical, which premieres and runs through September 20 at Hudson Backstage Theatre, Gayheart candidly shared her anxieties about the new venture. "Well, I’m scared shitless about singing. I’m just going to say that," she admitted. "I’m not a singer, so I have one solo and I’m really nervous about it. But at the same time, I am going to make it entertaining and fun. And if the singing isn’t amazing, it won’t matter, because the scene will be so much fun."

Stein expressed his excitement about reuniting with Gayheart, detailing the evolution of her character. "It’s so fun to have her playing the Carol Kane role," Stein said of Principal Sherwood. "Actually, in the musical, the Carol Kane role, Ms. Sherwood, and Pam Grier, the detective, are one role together. So, Rebecca, she’s the principal, but then she becomes empowered to sort of solve the case. So, it’s a really fun arc for that character that wasn’t in the movie."

Gayheart acknowledges the complexity of combining such disparate personalities. "So, it’s tricky because they’re polar opposites, as you know. Pam Grier and Carol Kane, it doesn’t get more different," she explained. Her approach is to "find it for myself, make it my own," highlighting that her Ms. Sherwood undergoes a significant transformation throughout the play, not unlike the film's character Fern Mayo/Vylette.

This onstage evolution for Principal Sherwood includes a solo number, complete with whip-cracking choreography by Jay Jackson, known from RuPaul’s Drag Race.

![AJ Paramo as Fern Mayo/Vylette and Rebecca Gayheart as Principal Sherwood in rehearsal for 'Jawbreaker The Musical'](https://deadline.com/wp-content/uploads/2026/09/0v6a1966_720.jpg "AJ Paramo as Fern Mayo/Vylette and Rebecca Gayheart as Principal Sherwood in rehearsal for 'Jawbreaker The Musical'")

Looking ahead, Gayheart even has a dream cast in mind for future runs of the musical. She hopes that her former Jawbreaker co-stars—Julie Benz, Judy Greer, and Rose McGowan—might take on the role of Ms. Sherwood if the musical ever makes it to the West End in London. "I think it would be amazing, and I think it would be really fun to see all of us in our different ways of doing it, and exciting for fans of the movie to see all of us come back and return," she shared.

Reflecting on the enduring appeal of the original film, Gayheart noted, "It’s pretty incredible that 27 years later, this movie is still relevant, and Darren Stein kept it timeless. I think that’s why every generation keeps finding it, and the message in the movie is really relatable for so many genre, types of people." She describes the film as a "heartfelt dark comedy."

Despite having previous Broadway experience in Steel Magnolias and Boeing Boeing, Gayheart finds the musical format a new frontier. "Doing a play, even on Broadway, is so different than doing a musical. I don’t even understand some of the language they use... So, I’m out of my comfort zone. It’s a journey. It’s exciting, but it’s scary and it’s fun."

![Rebecca Gayheart as Principal Sherwood and director Matt DiCarlo in rehearsal for 'Jawbreaker The Musical'](https://deadline.com/wp-content/uploads/2026/09/img_6813.jpg "Rebecca Gayheart as Principal Sherwood and director Matt DiCarlo in rehearsal for 'Jawbreaker The Musical'")

When asked about the announced Urban Legend reboot, a film in which she famously played the villain Brenda Bates, Gayheart expressed interest. "I would be open to it because I really love Brenda Bates. I think she was ahead of her time. I love that they let a female be a serial killer, and I think she was justified in her actions. So yes, I’m open to it if it’s done right and they stick to the tone of how we originated the movie. I would absolutely love to be a part of it."

Rebecca Gayheart, Julie Benz and Rose McGowan in ‘Jawbreaker’ (1999)