Interview: Julia Lester on Being the Last Little Red Stephen Sondheim Sent Into the Woods

When Stephen Sondheim chose Julia Lester for the two-week Encores! run of Into The Woods, he didn't know he was both handpicking his last Little Red, and poising the then 21-year-old to make the most auspicious Broadway debut a young actor could dream of.

Following rave reviews and overwhelming demand for more of Lear deBessonet's picture-perfect revival, the production has moved over to the St. James Theatre for a limited summer run where Lester now performs alongside a dream cast whose list of Tony Awards and nominations could choke a giant. To top off this Broadway fever dream, Lester also shares the stage with her lifelong musical idol, Sara Bareilles, who may still not know the extent to which she has shaped the life and career of the young woman playing her hungry, mischievous neighbor.

Lester first stepped into the spotlight on Disney's High School Musical: The Musical: The Series as Ashlyn, an aspiring singer-songwriter who took center stage as Belle in season 2's rendering of Beauty and the Beast. Not only is the character made in Bareilles's image, but Lester landed the life-changing role with a performance of Bareilles's "Gravity." She now finds herself going Into the Woods with Bareilles eight times a week, just as High School Musical's third season, landing on Disney Plus July 27, takes her and her TV castmates to summer camp. For one peculiar passing moment, Lester's magical worlds are colliding in the woods. And as Sondheim taught us all, that's what woods are for.

[This interview has been edited and condensed for clarity.]

Congratulations on your Broadway debut! Take me back to the beginning with this production. How did the opportunity to play Little Red at City Center originally come your way?
It was just another one of those self-tapes that came through. But of course this time it wasn't just another self-tape. It was Into the Woods at City Center with Sara Bareilles and all these amazing people. And I know that Little Red and Jack were two of the only, if not the only parts that they held auditions for. So I sent in a tape and about two weeks later my agents called me and opened the conversation with, "Stephen Sondheim wants you to play Little Red." I burst out crying.

Did you ever get to meet Sondheim?
He passed away before we started the Encores! production so unfortunately I never got to meet him or thank him for this incredible opportunity. But it's been amazing feeling his presence throughout every performance that we've done. He was such a huge supporter of everything since day one so I could really go into the show thinking, "I guess I really do belong here because Steve himself saw my tape and wanted me to play this part."

Do you have any personal history with Into the Woods ?
My community theater did Into the Woods when I was about 9, so I have this sort of familial bond with the show. I was actually Milky White, which was one of the best parts I've ever played. And then I have two older sisters, and my middle sister was Little Red and my oldest sister was Baker's Wife. While we were doing that show, I would rewatch the PBS special taped performance daily with my sisters. It was our favorite thing to do.

Since this whole process has been so fast, did you have to come in with your Little Red ready to go, or were you able to work with your director, Lear deBessonet, on your character in rehearsal?
I did have to come in prepared because there's not a lot of time to dive into things the way you would during a normal show process. But something that I was really grateful for was the time that Lear took to talk to us about our characters when time permitted.

I remember specifically working on my scene with Gavin Creel, who plays the Wolf and Cinderella's Prince. "Hello, Little Girl" has been kind of a controversial song depending on the way it's portrayed. In the original production, it had this haunting, eerie, honestly inappropriate connotation to it. That was something that Lear did not want to depict in our version of "Hello, Little Girl." So we had a sit-down conversation of, What does this actually mean? Little Red is attracted to the mysterious, mischievous, eerie part of the Wolf, and it's not the other way around. The Wolf views Little Red as a meal and nothing more than that. Lear is extremely conversational with all of the characters and rather than pushing her ideas out and seeing if they stick with her actors, she lets us make the first move and watches our natural instincts and allows a conversation to be built around that.

We have to talk for a second about working with Sara Bareilles. I've watched old interviews of yours, long before Into the Woods came into your life, and in several of them you call out Sara Bareilles as your favorite singer and personal idol. Do you feel like you manifested this job?

I mean, I do try to manifest. But I don't think I could have imagined manifesting working with Sara Bareilles. I still really can't grasp the fact that I see her every day and we get to do a show together. I sang one of her songs for my High School Musical audition, which then inspired the whole arc of Ashlyn wanting to be a songwriter. Ashlyn's inspiration is Sara Bareilles as well, which I always thought was so personal to me.

Does she know that about your High School Musical character?
I don't know if she knows that part yet. There are a lot of things that I have to work up to. I still get so nervous around her sometimes. I knew that I wouldn't be able to gush in person — I would stumble over my words and just not really convey how I feel about her. So I handed out opening night cards to the Encores! cast. You can't fit 15 years of love and gratitude into a tiny little card, but I did try and convey at least some of what she means to me. I knew she was an amazing person but she has exceeded every expectation. The morale that she brings, and the humility and humor and fun and heart. I couldn't have asked for a better leading lady to look up to. It's a dream come true and I will say it over and over and over again. And the Ashlyn conversation will come eventually.

In the midst of your Broadway debut, you've also got season 3 of High School Musical: The Musical: The Series coming out July 27. I know the Wildcats are going to summer camp this season. Did shooting it feel like summer camp?
I think that anybody you talk to from the cast will say that this is our favorite season. It was the most fun I've ever had. Season 1 was sort of the creation of it all. It was insanely fun, but it was also very technical. And then of course season 2 was extremely hard. We were in the midst of covid pre-vaccination in Utah, isolated alone. The show itself still held its ground and was beautiful but it was very high intensity. So coming into season 3, which we filmed in Los Angeles, and being like, "Oh my god we're at summer camp and things have loosened up a little bit, and we're at home and comfortable," it just was the perfect recipe for the most fun, perfect season. We filmed the majority of our time at a real family-owned summer camp, we were outdoors, we were hanging out, we were exploring, and it felt like real sleepaway camp. We created a new family with the new characters and our crew and I think it'll be extremely apparent that we were just having a ball.

I can't talk about High School Musical without talking about Miss Jenn (played by the incredible Kate Reinders). The show is so much about her and her impact on all of her students, so I always end my interviews with High School Musical folks with the same question: Who has been your most influential teacher?
Honestly, Tim Federle, our show runner is an amazing mentor in my life. I want to have him with me for the rest of my life in everything that I do. But because we're on the topic of Miss Jenn, I have learned so much from Kate Reinders. I have admired her forever. I saw one of her very first previews of Something Rotten! on Broadway, which was at the St. James where I'm performing now, which is insanity. We call her Mama, and she really is such a parental figure for all of us. We were all living alone in Utah and she was really there to be this steady rock for all of us to cling onto when we needed her. I have learned so much from her, not only about acting and performance, but just how to be a gracious person. I think that she is an angel on this Earth and I have gathered so much vital information from her the last four years I've known her. I just want to gush about her all the time because she really is the real-life Miss Jenn.