The interview was recorded in March 2024 and has been edited for clarity and conciseness. This article is the second of two parts.
The Chronicle (TC): Speaking of ‘Anyone But You,’ what was the inspiration behind the script? How did you approach adapting Shakespeare into a modern rom-com?
Ilana Wolpert (IW): It’s based on ‘Much Ado About Nothing,’ my favorite Shakespeare play. At Duke, I was studying Shakespeare intensely and even thought I’d go into academia. I was in Antic Shakespeare, a theater group, and I studied at the Globe in London.
When I started writing movies, it felt natural to base one on a Shakespeare comedy. So many of my favorite films — ‘10 Things I Hate About You,’ ‘She’s the Man,’ ‘Clueless’ — are modern adaptations of classic stories.
Jacqueline Monetta (JM): Ilana is a Shakespeare fanatic. There's no one who knows Shakespeare better!
I wasn’t always a Shakespeare person, but I loved the adaptations. ‘She’s the Man,’ ‘10 Things I Hate About You,’ even ‘The Lion King’ — all are based on Shakespeare plays. It was so cool to work on a film like that.
TC: Jacqueline, as a producer, what criteria do you go through when selecting a film to produce? And what is the process of getting a script picked up by a producer?
JM: Every script is different. Sometimes it's a pitch, sometimes it's a book or just an idea. For’ Anyone But You,’ I remember hearing that Sydney Sweeney and Glen Powell had attached themselves to a modern adaptation of ‘Much Ado About Nothing,’ and I thought, Oh my God, this sounds amazing! That afternoon, I reached out to Will’s team — he’s represented by UTA, which is how I ended up working for him — and UTA also represents Ilana. We got the script that evening, I read it that night, and the next day, Will and I talked about how we had to make this movie.
For me as a producer, I always look for projects that feel theatrical, fun, and have a sense of nostalgia. I want to make movies that I would love to watch. At Olive Bridge, we always prioritize big ideas, unique stories and character-driven narratives. Every movie we work on is one we’re genuinely excited about.
TC: Ilana, how was writing for ‘High School Musical: The Musical: The Series’ different from writing a feature film? How was it turning a beloved IP into a TV show?
IW: Writing for TV is different from writing features because you’re working within episodic constraints. In a feature, you can expand the world more and have more time to explore characters. In TV, especially in ‘High School Musical: The Musical: The Series’, we were working within the limitations of a high school setting. But I love both formats equally!
TC: As a writer or a producer, how closely do you work with the casting process? How involved were you with the key actors?
IW: For ‘High School Musical: The Musical: The Series,’ I didn’t work very closely with Olivia Rodrigo. But Sydney was a producer on Anyone But You, so I got to know her through that process.
JM: As a producer, casting is a big part of the job, and it’s one of my favorite processes. For “Anyone But You”, Sydney and Glen were already attached when Olive Bridge and Will came on board. But for the rest of the cast — Darren Barnet, Alexandra Shipp, GaTa, Dermot Mulroney — we worked closely with Will to decide who fit the roles.
On set, my job was to make sure Will and the cast were happy and working together seamlessly. It’s a lot of collaboration, and I was on set almost every day.
TC: How surreal was it to see “Anyone But You” go into production? How did it feel seeing it come together at the premiere?
IW: It was amazing. It takes so many people to make a movie happen, and it’s surreal to think that it all started with me sitting at my computer during the pandemic, trying to escape reality by writing. The experience was incredible, and the premiere was so special. It still hasn’t fully hit me that we made a movie!
JM: The production process was such an amazing experience. The cast had great chemistry, and we did so many fun bonding activities — ropes courses, movie nights, dinners, even attending the Sydney Pride Parade. We were constantly together, even on our day off.
Seeing the movie gain traction, especially on social media, made it feel real. When we saw Anyone But You trending all over TikTok, that was a moment where it really hit me.
TC: How do you handle the public reaction and newfound attention that comes with success?
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IW: Well, my Letterboxd account has a lot more activity now! I posted a five-star review of Anyone But You, jokingly acknowledging my bias since I wrote it, and suddenly I was getting comments from teenagers saying either, Never write again, or This was amazing! It’s been amusing.
JM: We’re laughing because our day-to-day lives haven’t changed much! We’re busier, and we’re getting more rom-com scripts sent our way, but it’s business as usual. It’s exciting to see people respond to the film, though.
TC: What’s next for both of you? Any upcoming projects?
IW: I’m currently writing for a new Amazon series about a group of kids who start a band after high school. I’m also developing more rom-coms and have some exciting projects in the works.
JM: We’re producing a lot at Olive Bridge. Will’s next film is a comedy with Apple, hopefully shooting this summer. We’re making The Aristocats remake for Disney, adapting the Just Dance video game into a movie and producing a Netflix series based on Holly Madison’s Playboy Mansion story. There’s a lot going on!
TC: That sounds amazing! Thank you both so much for your time.
Arnav Jindal is a Trinity sophomore and culture editor of The Chronicle's 119th volume.