For Kaitlyn Dever, ‘Rosaline’ Was Worth the 10-Year Wait: ‘It’s Not Something I’ve Really Done Before’

“The more and more I thought about it, the more I thought Rosaline was maybe just a really heightened version of myself,” the Emmy nominee said

Kaitlyn Dever as Rosaline in 20th Century Studios' Rosaline, exclusively on Hulu. Photo courtesy of 20th Century Studios.
Kaitlyn Dever as Rosaline in 20th Century Studios' Rosaline, exclusively on Hulu. Photo courtesy of 20th Century Studios.

Kaitlyn Dever may embody one of literature’s most overlooked characters in “Rosaline,” 20th Century Studios’ campy and modernized retelling of William Shakespeare’s “Romeo and Juliet” from the perspective of the forgotten Capulet, but the Emmy-nominated actress is anything but. 

Earning her first executive producing credit on the Hulu film (based on Rebecca Serle’s book “When You Were Mine”), the “Dopesick” star continues her ascent in Tinseltown, setting her sights on directing next and gushing about being featured opposite rom-com greats Julia Roberts and George Clooney in “Ticket to Paradise,” which debuts next week, in a recent interview with TheWrap.

“When I approached Rosaline, the way I developed the character and the process behind bringing this character to life was just really pushing any boundaries that I had been afraid of before,” Dever told TheWrap, “because Rosaline has an intensity and her intensity is the drive throughout the story in the film, and I think that it’s not something I’ve really done before. It’s not something I’m necessarily used to.” 

Though, it might be something that comes easier in time.

Dever, who first broke out with 2019’s wildly funny “Booksmart,” first read the script for “Rosaline” at 15, sending in an audition — for Juliet — shortly after. The 25-year-old then played the waiting game, always wondering what happened with the project until she got a call about it in 2020.

“I just remember loving it so much, and it was unlike anything I’d ever read before, and it’s such a great idea,” she said. “And then nothing happened with it and I always wondered — I always wanted that movie to get made and I was so excited for it to get made, even just to see it as an audience member because I just loved the story so much. And then I was shooting something about two years ago and I got a call and they were asking if I wanted to play Rosaline: The story I had been thinking about for forever and I couldn’t believe it that they were even considering me to play her and to take on that kind of role.”

It was after her initial audition for “Rosaline” that she met its scribes, longtime writing partners Scott Neustadter and Michael H. Weber (“(500) Days of Summer”), on the set of the heart-wrenching 2013 indie “The Spectacular Now,” in which she played Kristal. Then, “Yes, God, Yes” helmer Karen Maine was brought on to direct. 

“I love the both of them and their collaboration and how they write and their style and everything,” Dever said of the duo, adding, “And then the filmmaker, Karen, is someone that immediately understood Rosaline so well, and we agreed on so many things and it was just an immediate connection that Karen and I had. I think she just really understands comedy and subtle comedy, and tackling the emotional parts of this movie.”

In many ways, “Rosaline” offered Dever a blank canvas; while the character is mentioned in Shakespeare’s seminal play, the ink runs dry on her essence and motivations. As an executive producer, along with the likes of Shawn Levy (“Free Guy”), the actress and Maine crafted the eponymous character to move beyond the movie’s cheeky tagline, “Meet Romeo’s Ex,” and embody a holistic, forward-thinking person. 

“I wanted to represent all the parts of her: She’s a total feminist and ahead of her time and she has so much drive and dedication,” Dever said. “She’s a person that is completely rejecting all the gender restrictions that were put on women at that period of time. So I wanted to represent all of these parts of her while really focusing on the comedic moments and the comedic timing.”

(L-R): Spencer Stevenson as Paris, Kaitlyn Dever as Rosaline, Kyle Allen as Romeo, and Henry Hunter Hall as Mercutio in 20th Century Studios’ ROSALINE, exclusively on Hulu. Photo by Moris Puccio.

As Dever and Maine shaped the character out of canon and using the script as a guide, Rosaline’s grit and free-spirited energy was naturalistically born out of the star’s own personality. 

“Creating this role with Karen was just my favorite thing ever, doing that on a daily basis on set, and she really allowed me to feel free in that and try different things,” the actress recalled. “The more and more I thought about it each day on set, the more I thought Rosaline was maybe just a really heightened version of myself.”

Being involved behind the camera for the first time and getting into the filmmaking process on the ground floor also helped Dever guide the film’s narrative beyond Rosaline, while also informing her of the next steps she wants to take in her career. 

“The fact that this story is told from a female perspective, I was so honored that they allowed me to come on board in that kind of way,” she said. “Directing is something that’s very much on my mind recently and this, I feel like, has been a really great experience to just learn. Obviously, I learn so much as an actor — being on set and collaborating with producers, directors and writers — but I think being involved in the early stages of a project really is so informative. I love being part of the process; the casting process, and the early stages of making a movie is so cool. I’m forever grateful that they allowed me to be an executive producer.”

While “Rosaline” comes from a storied tradition of revamping the Elizabethan era playwright’s works — with adaptations on a sliding scale of reinvention from “Rosencrantz and Guildenstern Are Dead” to Baz Luhrmann’s “Romeo + Juliet” and ‘90s teen classics like “Clueless” and “10 Things I Hate About You” — Dever said the “unique feel” of the script enables it to feel like a “standalone” movie.

“What we were trying to do with ‘Rosaline’ was something fresh and new because that’s what the script called for,” she said. “It called for a brand new, exciting take in this kind of world, essentially. I was also just thinking about comedies and romantic comedies in general that I sort of grew up on, like ‘The Princess Bride’ and even [laughs] I mention ‘Ella Enchanted’ just because it was one of my childhood favorites, and because Minnie Driver is in that movie — I was just over-the-moon excited when she got attached to play the nurse in this movie.” (Driver delivers several excellent line readings as the aforementioned nurse, where she is forced to explain her medical qualifications in abundance — something that particularly comes in handy when reimagining the “Romeo and Juliet” death scene.)

Dever recalled the climactic scene — which is subverted to hilarious ends and took two days to film — as one of her favorite on-set experiences: “That whole scene, there’s just so many actors to cover and so much dialogue. I just find it sometimes so funny when there’s a bunch of actors in those kinds of costumes, [we] get together and [we’re] being all so dramatic. It was one of those days that if I wasn’t laughing, someone else was laughing. Bradley Whitford and Christopher McDonald were just always on fire with their comebacks and their ad libs,” she said, adding that she “really appreciated” how “everyone really put 100% of their effort” into its making.

Next up, Dever will appear as the daughter to Clooney and Roberts’ divorced couple in “Ticket to Paradise,” who travel to Bali in an attempt to sabotage her upcoming nuptials. Coming up exactly a week after “Rosaline’s” release, it’ll mark the first major theatrical rom-com release for either star in over a decade.

“They’re both in the same fun, feel-good realm that I think everybody is looking for in movies right now,” Dever said of the films. “So it’s really exciting to be able to talk about both of these projects that I love so much, and getting to be in a movie with George Clooney and Julia Roberts is also not bad [laughs]. I love both of them so much and have looked up to them for so many years and I’m just so grateful I got to just be in scenes with them and act with them and learn from them.”

“Rosaline” is now streaming on Hulu.