By: Adam Shiff ’24
Ilana Wolpert ’11 joined Pine Crest School as a fifth grade student. A former runner, Ilana has fond memories of early morning practices, riding the bus with her three best friends (of 20 years now), circle pizza and rolling cheese in the dining hall, and the first time she was told that she could be a writer.
After graduating from Pine Crest, Ilana earned her undergraduate degree in English and theater studies at Duke University. “I focused on Shakespeare studies,” said Ilana, “and during my senior year, I took a screenwriting class. That is where things clicked for me—I knew that was what I wanted to do.”
Ilana’s appreciation for Shakespeare and the classic literature genre began as a seventh grade student. “Ms. Brown, my seventh grade English teacher, was my favorite teacher at Pine Crest,” she said. “She really cared about her students and discovering their strengths. She was the one who really encouraged me and told me I was a writer. That was the first time it sparked anything for me—I was always interested in writing, but no one really told me anything about myself until Ms. Brown did. That was special, and I feel that year was the year that I also became really infatuated with looking at books in a different way and thinking about them and really embracing them.”
“I had always been very into Shakespeare,” said Ilana. “His work always resonated with me. Some of my favorite teen movies are inspired by Shakespeare, like the romantic comedy ‘Ten Things I Hate About You.’”
“‘Much Ado About Nothing’ is my favorite Shakespearean piece, and I kept coming back to it at school, even throughout my studies in college,” Ilana continued. “I believe this is the original ‘enemies to lovers’ romantic comedy. There is so much farce, great humor, and so many great characters. It's about family and friendship, but also a battle of wits and genders. It's really a wonderful play. I always felt it would make an amazing movie.”
Ilana recalled being overcome with a special feeling during her senior year at Pine Crest when she wrote for Spring Scenes, a student-produced, off-campus performance. “When I wrote my scene for that, it was the first moment I thought ‘oh this feels really good, and this is really fun, and I love this experience.’ It was very affirming—I just wasn’t sure what the path was to becoming a professional writer, and a lot of it I had to figure out by just going for it.”
As Ilana explained further, “I always had an inclination that writing could be in my future, but I was not sure in what capacity.” With the help and encouragement from her best friend, Ilana moved to Los Angeles without a job but with the dream to write for TV and film. “I got very lucky and landed a job within a few weeks of moving there as an assistant,” she said. “I have been here for eight and half years now.”
Though she secured a job, success in the industry did not come overnight. Ilana worked as an assistant for four and a half years. Over the summer of 2019, she sold a show and subsequently got hired for her first writers’ room as a full-time writer. “For me, my first big break was getting an initial meeting with a production company who knew me as a writer and not just as an assistant,” she said. “It was then that the screenwriting for the movie evolved.”
“The movie” she referred to is “Anyone But You,” based on the idea Ilana had long carried with her of an adaptation of “Much Ado About Nothing.”
Combining her love of the classics with her literary creativity, Ilana explained the direction and approach behind the story that evolved into the major motion picture, “I wanted to transport audiences back to the ’90s and early 2000s, immersing them in something that felt good and timeless. I wanted it to be classic while still feeling fresh and modern. But we were very intentional about not time-stamping the movie in 2023. You don't see technology, you don't see Instagram, and not many iPhones; it's very centered on people being present in a moment in time.”
Actors Glen Powell and Sydney Sweeney are the star duo teaming up for Ilana’s big screen movie debut. Sweeney was the first to be cast. “We wanted to find the right female lead for this because it is based on Shakespeare, and she was very excited about the part,” Ilana said. “One day, Sweeney called and said ‘What about Glen Powell for the lead role?’ and we all loved the idea. Once the two of them were on board it was very easy to get a director attached and sell it to the studio. It seemed like all of a sudden, we were off to the races—starting pre-production, and people were moving to Australia. It was like ‘oh my God—we're making a movie!’”
Though the movie debuted recently, in December 2023, Ilana is already moving onto future projects. While in Los Angeles, she has also been credited as a writer for the CW show “Crazy Ex-Girlfriend,” and “High School Musical: The Musical: The Series,” on Disney+. Judging from her work, her future projects are sure to bring Ilana great success!