Rosaline Review: Kaitlyn Dever’s Talent is as Boundless as the Sea

O Kaitlyn, Kaitlyn, wherefore art thou Kaitlyn?

“Main character syndrome” is a phrase that I first saw on TikTok — not something I’m proud to admit — but I think is relevant to this conversation about a new film set to hit Hulu this Friday. Everyone knows at least one person, whether it’s from school or just someone in our daily lives that thinks that they are the main character of everyone’s stories. In reality, most of these people are mere supporting characters. As Rosaline shows us, this same complex existed back in the 14th/15th centuries in a film about a character in the classic Romeo and Juliet story that would be no more than a footnote in that story — despite what the last line of this film may suggest. 

There was almost a world where Romeo and Rosaline would have been the duo that led a staple of high school English classes — at least according to Rosaline (played by the uber-talented Kaitlyn Dever) herself. Never heard of her? Well, Rosaline was Romeo (Kyle Allen)’s original love who, after being stood up at a masquerade party, begins exploring new options including Rosaline’s cousin Juliet (Isabela Merced). However, let’s not put the cart before the horse, as Romeo and Rosaline were up to the same shenanigans that you’ve grown to know Romeo and Juliet for. The two exchanged letters — it’s been well-documented that Romeo is the Cyrano de Bergerac of this world — and snuck up to each other’s balconies under full moons at night. But due to the conflicts between the Montague and Capulet families, the two are forbidden from each other. Yet, as history has shown us, we all want the forbidden fruit — that is half the fun, after all — and the elaborate relationship comes to a head once the events of the masquerade party mentioned above occur. 

(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. © 2022 20th Century Studios. All Rights Reserved.

But as the saying goes: when one door closes, another opens. Rosaline, during her efforts to steer Juliet away from Romeo, meets a handsome sailor named Dario (Sean Teale). Dario doesn’t come from royalty as just about every other character in the film does, but he does have a charm about him that would make any girl — except Rosaline in the early goings of this film — desire him. The two start off on rocky terms, with Juliet being taken aback by Dario’s ability to take it as much as he can take it, before finally beginning to come around to each other as the film progresses.

Rosaline, the character, is a bit of unchartered territory for Dever; who’s usually the one being chased, not the jealous ex. Rosaline not speaking in a British dialect allows Dever’s signature sarcasm to shine in a film with plenty of wit and sarcasm. Admittedly, the character of Rosaline is not always the most flattering — something that can’t be said of many of Dever’s characters — yet the actress playing her clearly embraces that. Simply put, Rosaline is a narcissist who is always looking out for herself. She even goes as far as to take on a “big sister” role of sorts for her younger cousin Juliet. Rosaline is so self-centered that she is so hyper-focused on the wrong guy while the right one could just be standing right there. 

We’ve now covered nearly all the ground with Dever’s versatility as an actor. She has tackled comedy (Booksmart), drama (Dopesick), rom-coms (Ticket to Paradise), oh, and she’s a damn good singer (shoutout to Beulahbelle). Anyone who knows me is aware — and likely sick of me reiterating — that I’m a big believer in Dever and think she can do no wrong. She saved the trainwreck that was that film adaptation of Dear Evan Hansen and made it watchable and I think she should be allowed to pick any project she wants regardless of the ridiculousness of its premise as a reward for that.

And that’s exactly what Rosaline is. When it’s firing on all cylinders, it’s a meta satire of the Romeo and Juliet story. Perhaps a bit on the nose, but this is akin to how the Scream films mock horror films of yesteryear. And I think it’s necessary to lean into that lore because the character of Rosaline is no more than a footnote in Shakespeare’s play. 

Creating a film about an unseen side character in one of the most iconic literary works ever is a bold move by director Karen Maine and screenwriters Scott Neustadter and Michael H. Weber; who wrote their screenplay based on the novel, When You Were Mine by Rebecca Serle. When done correctly, you get a film like Rosaline. On the flip side, you also inherit the risk of making a film about a side character no one cares about. Imagine a Star Wars film revolving around Boba Fett, oh wait…

(L-R): Kaitlyn Dever as Rosaline and Sean Teale as Dario in 20th Century Studios’ Rosaline, exclusively on Hulu. Photo by Moris Puccio. © 2022 20th Century Studios. All Rights Reserved.

And a special shoutout to Nico Hiraga is deserved, who plays Steve the Courier, the first Shakespearean stoner. Hiraga was one of the standout side characters in Booksmart — one that likely wouldn’t require his own story despite how intriguing his journey at an Ivy League school would be — and once again steals the show in Rosaline. He’s like that one roommate that you repeatedly tell to fill up the Brita pitcher and despite the “I will” they give you in response, you know deep down that they aren’t going to do it. 

Fortunately, Neustadter and Weber never lose sight of what Rosaline is: a rom-com. The film is written as such and sure, if you’ve ever seen a rom-com, I can guarantee that you can gess the story of Rosaline beat-for-beat. Should that bother you? Not in this case. After all, there is a reason that there are formulas in this world, and that’s because they work. In the superhero genre, cookie-cutter films are less excusable. In a rom-com, however, you can only take so many swings. Plus, I’d also argue that placing a rom-com in the world of Shakespeare is already a big swing — much less revolving a story around a footnote in one of the most iconic plays of all time.

(L-R): Isabela Merced as Juliet, Mercedes Colon as Lady Capulet, Alistair Toovey as Tybalt, Bradley Whitford as Adrian Capulet, Christopher McDonald as Lord Capulet, and Kaitlyn Dever as Rosaline in 20th Century Studios’ Rosaline, exclusively on Hulu. Photo by Moris Puccio. © 2022 20th Century Studios. All Rights Reserved.

The set design and aesthetic of a film like Rosaline are vital to its success in pulling the audience into this medieval world. Sure, it has a few sequences — namely the sequences on a boat — where it’s clear that this was shot on a soundstage, but the castles of the Montague and Capulet families are mesmerizing despite how little of the scope we get to see, as are the costume designs (shoutout to Mitchell Travers, whose work is stellar). Despite the small number of occasions that the sets and costume design can be showcased together, the two party scenes in the film do them justice.

I’m not going to sit here and act like Rosaline is a game-changing rom-com or satire. Heck, Ticket to Paradise may trump this film as Dever’s best performance of the year later this month. But Dever continues proving that her talent is as boundless as the sea. I’d argue that she’s currently on a level where any film is watchable with her presence (again, I can’t emphasize enough how much she elevated Dear Evan Hansen a year ago), and thou shall watcheth Rosaline for that very reason.

Rating: 82%

Rosaline will be available to stream exclusively on Hulu on October 14.

Andrew Korpan

Andrew Korpan

Film "critic" and entertainment journalist whose work has been featured in Above the Line, Below the Line, Collider, /Film and Coastal House Media.
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