How Julia Lester Went ‘Into the Woods’ and Came Out a Broadway Star

When her agent calls, “I never know if it’s going to be a good thing or a bad thing,” the actor Julia Lester said. Last August, one such call came through, and it turned out to be life-changing.

A few weeks before, Lester, 22, had auditioned to play Little Red Riding Hood in a forthcoming production of Stephen Sondheim’s Into the Woods. She recalled to The Daily Beast that she had sent a self-made tape of herself singing the character’s song “I Know Things Now,” and performed three additional scenes fully dressed up as the character sticking a red skirt under her collar to make a cape, and brandishing a knife to ensure producers knew she was ready to face the hungry Wolf.

“Part of you doesn’t want to hold on too tightly, you don’t want to get your hopes up,” Lester said of waiting to hear after the audition. She had other job possibilities floating about. But on the call that day, both her agents were present. “If they’re both on a call, you know it’s big news,” Lester said. “I thought, ‘Whatever can this be?’ One of them said: ‘Sondheim wants you to play Little Red.’

“It’s a sentence I will never forget,” said Lester. “I immediately said, ‘Shut up, shut up, no way no way.’ I was like, ‘That tape I made in my bedroom was seen by Stephen Sondheim and he wanted me to be part of this?’ It was very exciting.”

Stephen Sondheim’s ‘Into the Woods’ Is Sheer, Moving Magic on Broadway

Next, she FaceTimed with her parents and sister, all of whom are actors and performers. They all screamed. Then Lester, also a star of High School Musical: The Musical: The Series, had to wait seven months for the critically acclaimed Encores production, “a long game of anticipation and excitement”—which then transferred to Broadway’s St. James Theatre, critical acclaim not only intact but even more fervent. The production—beautifully performed and directed, and hilarious and profound in equal, well-judged measure—is proving so popular with audiences that it keeps being extended, now to Oct. 16 with additional extensions possible.

“I don’t know if you can tell, but we’re having so much fun in the show,” Lester said. “It’s really amazing. We were at Encores for a two-week engagement, and we didn’t want to think beyond what we had to do at the time. But from the second we started, we all thought, ‘This is really special and it deserves more than the life it’s being given now.’ We just didn’t know in what capacity.” Working on Broadway is always an actor’s dream, said Lester, and here she is in a hit show in both her New York and Broadway debuts—every extension to date has been an additional cherry.

Lester never met Sondheim, who died aged 91 last November, so doesn’t know why she was his choice, “but he was a massive cheerleader of the Encores production. He had a big part in handpicking who was going to be in the show, and knew the show backwards, forwards—he wrote it! It’s the highest form of praise to know he saw my tape and said, ‘That is somebody I want to play that part I wrote.’”

Her character, and her performance, excite loud appreciation from audiences. Her Little Red is streetwise, sassy, wry, and then—as the play deepens—revealed as a young girl yearning for the profound connection with others, and the imperiled world they live within, that the musical is centered around.

The ecstatic, uproarious responses at the end of both acts of the show “is a really electrifying feeling for all of us. That’s the goal of theater—to get that response from an audience,” said Lester. “And it’s such an honor to be singled out in such a stacked cast, whether in reviews or by people on the street who catch me on my way to dinner and say lovely things about my performance.

“Performing in New York or Broadway is this distant dream. You never know when, if, where, when, or why it’s gonna happen. All of these factors contributed to my debut—along with Sondheim, this incredible cast and creative team. Everything around is bigger and better than anything I could have pictured for my New York debut. I’m so very lucky and grateful.”

“I’m a diehard theater kid at my core”

Lester was really only ever going to be an actor: her parents (Kelly and Loren Lester), her sisters Jenny and Lily, and her grandparents are all performers. She grew up “thinking that everyone became an actor.” If she’d been passionate about anything else, her parents would have supported her. “But I fell in love with acting the second I was introduced to the world of musical theater and world of acting. I have been constantly immersed in it my whole life.” As a child, she loved movies about heroic young girls—Dorothy in The Wizard of Oz, Matilda, and The Little Princess. “I saw them, and thought, ‘I want to be doing that, being dramatic like that.’”

The luxury of growing up in a household of performers was “having acting, singing, and dancing coaches wherever I looked. I didn’t have to leave the front door to get wonderful advice about performing. I was very theater-focused, not academic. Most of my time in school was spent daydreaming about what show I was going to be in.”

The only other thing Lester thought about becoming was a makeup artist; that art, after all, goes hand-in-hand with performance. In 11^th grade, she played the Beggar Woman in a production of Sweeney Todd, creating her own prosthetics and blacked-out teeth.

“My very first lead role was as Éponine in a community theater production of Les Misérables,” Lester recalled. “I took that role so seriously. I’m not encouraging this, but I remember in math class instead of taking notes I would be drawing stage designs, writing out lyrics, blocking scenes, and drawing sketches of Marius and Éponine and their forbidden love. I loved being serious about the dramaturgy of it all.”

A year and a half later Lester won the title role in Carrie: The Musical, which was “very challenging, and a moment I really believed in myself. I had never had that responsibility of having to carry a show from beginning to end. I had a very supportive cast and crew. That show solidified who I was and that I could have a future in this industry. That part was so special to me. I created a shrine of Carrie above my bed with posters and notes from the cast. That show was everything to me.”

The role of Little Red in Into the Woods has grown and evolved from her initial conception, alongside the casts Lester has worked with, and director Lear deBessonet. “I definitely knew this Little Red would be different and unexpected when you think of the norm—the sometimes whiny, troubled young girl she is seen as. I always knew and carried a different, nuanced version of her.”

For instance, when it comes to the relationship of Little Red and the Wolf, deBessonet asked Lester and co-star Gavin Creel (“an angel, I adore him”) how they interpreted the relationship. “Lear made it clear that for her it wasn’t a predatory storyline in any shape or form. If anything, Little Red is intrigued in that regard by the Wolf. He just sees her as a meal. He’s just hungry. That makes sense for when she sings ‘I Know Things Now,’ and Little Red coming into her own, whether that’s a sexual awakening or an excited awakening with the mysterious Wolf.”

The Encores run being so short meant rehearsal time was also staccato-short, and so Lester came with “clear, solid, and distinct choices” already made when it came to her character, knowing that had to be threaded into “Sondheim’s music, which is so insanely difficult, the choreography, staging, and script and storyline people know and love so well.

“One of the most important things you want to do with a revival is revive what has been seen before. When going through the script on my own, I went through every single Little Red line and asked, ‘How can I make this completely different to what anyone has seen before?’ I read every line out loud and did the complete opposite of what my natural instinct was. I asked myself what the stereotype of what Little Red was and how I wanted to make her different, unique, and separate to what anyone has ever seen.” The voluble audience response to the wry, streetwise young woman on stage has led Lester to think, “Oh good, I’ve made the right choice of character.”

Lester also appreciates the journey her character goes on—from sassy and bratty to vulnerable as she realizes, along with everyone else, “no one is alone.” She and the rest of the cast are well aware of the emotional swings of the audience too: the laughter, then the crying and sniffling, especially at the end. “It’s so wonderful and fulfilling to know we brought them on this journey with us and we have succeeded in doing our jobs.”

Lester said she was extremely starstruck when first meeting the rest of the cast. “I’m a diehard theater kid at my core. All of these people are such experienced veterans of the Broadway world. I was really nervous and very intimidated about being grouped with them. I still feel all that, but I know them on a human level now, so can talk and joke with them. There was definitely a moment of imposter syndrome—‘Am I really allowed to be here?’”

Acting alongside the likes of Denée Benton, Heather Headley, Neil Patrick Harris, and Sara Bareilles helped temper the feeling. “Watching these people on stage is to see the end product of their work, not the process of getting there. Watching how they came up with those performances was very humanizing. It broke down the flashy, sparkly stardom of it all, and made me realize, ‘Oh, you guys are hard-working actors like I am. To watch that process first-hand was very grounding. It helped me be comfortable asking for help if I needed it.”

Like everyone else, Lester is watching the extensions the show keeps getting. “I would love Into the Woods to take on the life Chicago (the longest-running musical revival and the longest-running American musical in Broadway history) has taken on, and that it becomes a show which, when people come to the city and hear it is on, they think they have to get a ticket for it. I’ll be with the show as long as they will let me.”

Lester also keenly registers the political and cultural heart of the show—as it interrogates democracy, community, and what makes a family. “The first time it was performed was during the AIDS crisis, then it was performed after 9/11, and now it’s being performed, post-pandemic and amid everything else that is happening in this country,” Lester said.

“I think there’s a level of catharsis and release it offers to people, in how it resonates with their lives and things happening in the wider world. That’s what Sondheim does so beautifully. He takes these well-loved fairytale characters to tell a story bigger than themselves.

“One line constantly sticks out in my mind. When the Baker’s Wife has died, the Witch says, ‘Wake up, people are dying all around us.’ They’re not the only ones suffering loss. From the stage, you hear the gasps of the audience when she says that. That line rang true during the AIDS crisis, it rang true after 9/11, and it rang true after the pandemic. I think that’s why people are coming and enjoying it and getting so much from the show. It’s therapeutic.”

“I had to remind myself of who I was”

Alongside Into the Woods, Lester is also preparing to film season four of High School Musical: The Musical: The Series, happy that her character Ashlyn is taking a similar path to her portrayer in becoming “a diehard theater kid.” Showrunner Tim Federle, says Lester, takes inspiration from the actors’ lives in shaping their teen alter egos. Like Lester, Ashlyn also suffered from imposter syndrome when she was awarded the part of Belle in a production of Beauty and the Beast, wondering if she deserved the role.

“I don’t think that questioning ever goes away in anything you do,” Lester said. “There will always be a moment of ‘Why?’ But as you get older, you stop questioning, ‘Why me,’ and more why you are in the circumstances you are in. That’s something I have grown to know about myself. Self-doubt is a very real normal thing, and it will always happen. A lot of the performance industry is about ‘right place, right time.’ You have to trust the process,’ as Miss Jenn (from HSMTMTS) says.”

It is not strange, Lester says, being 22 and playing a high school student. “I have never played my own age before. In a way it’s nice I am older. I can nurture Ashlyn as a person and character because I have grown beyond what she is going through. It gives me a better understanding and acceptance of who she is. It helps me portray her in an authentic way because I have lived through it.

“Ashlyn is a lot younger than me, and is slowly learning as time goes on. And I am still learning to look at the bigger picture of how you get there and why all the trust, hard work, dedication, professionalism, and respect you put into the world will come back to you.”

This came from directly watching her parents when younger. Lester doesn’t know if it was an advantage, “or more a luxury,” that she grew up watching them at work on TV and theater sets, but that they “led their lives with kindness and respect” is something Lester seeks to emulate. Her family has come to multiple performances of Into the Woods, laughed, cried, and cheered her on. As we speak, her mother begins singing in another room. “There is always theater going on here,” Lester said, laughing.

Looking to the future is the best kind of mystery. Lester says she is “living the dream, doing two projects, one on stage and one on screen, one Sondheim, the other Disney. It can’t get any better than that. At some point, I would love to originate something one day, build a character from the ground up.” A writer of poetry since a kid, she has also “dabbled in screenwriting,” and so writing her own scripts is another dream, as well “having a family one day and raising kids.”

Performing remains her “biggest passion and where I feel most free and unapologetic and truly myself. It is my top priority, and I would love to continue that in any way possible.”

Lester recalls that as a very young child she had supreme confidence because “I had nothing to apologize for. Given the chance to perform, I did it broadly, loudly, and never apologized for who I was. Then you go through a phase of being a teen and young adult and you start to see yourself through other people’s eyes. My biggest enemy growing up, especially in high school, was living through the lenses of other people. I had to remind myself of who I was when I was little, when the world was my oyster, and there was no judgment—when I was living truly, authentically, with no question or qualms. As an adult, I try to remember who that little kid was, dancing on the coffee table with no apologies, and when nothing negative in the world could get to her.”

Lester paused. “It’s funny. When you get older you try to re-adopt some of the qualities you had when you were super-little. I definitely try to do that now. You think, ‘If I was able to do that then, what’s stopping me from doing it now?’”

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