Directed By: Karen Maine
Starring: Kaitlyn Dever, Isabela Merced, Kyle Allen, Sean Teale, Bradley Whitford, Christopher McDonald
Plot Summary: A comedic retelling of Shakespeare’s “Romeo and Juliet,” told from the point of view of Romeo’s jilted ex, Rosaline, the woman Romeo first claims to love before he falls for Juliet.
Much like a lot of plays written by William Shakespeare, Romeo and Juliet has been contextualized in very interesting ways. We’ve had a zombie version in Warm Bodies, a lavish musical West Side Story and hell, even Troma did a delightfully gross out version, Tromeo and Juliet, written by James Gunn. The list could go on and on. The last big generational take on the Bard’s most famous work was Baz Luhrmann’s 1996 Romeo + Juliet starring a young Leonardo DiCaprio. Honestly, as a pre-teen, this movie blew my mind, and I still occasionally play the iconic soundtrack. I only mention this because, I love that movie, and I always want to talk about it. But more to the point, I cannot recall another big budget adaptation that has had the kind of staying power.
When I heard the plans for Rosaline, which casts a light on Romeo’s girlfriend (who gets quickly dropped early on), I was pretty excited. It seemed like a really curious take on material that literally dates back to the late 1500’s. Is it worth checking out? Thankfully, yes. Much like The Princess, Rosaline is another attempt at rebranding heroines in period films with a modern girl boss twist. The latter statement might sound a bit cynical, however they are just cool power fantasies for girls, and that’s awesome in my opinion.

Rosaline is brilliant in how it wonderfully plays on what we think we know about the famous tale, yet puts a fresh spin on it. The movie is clever in how it subverts staples of the play at every corner. Notably, and most effectively, I adore how they re-frame Romeo as not this legendary lover, but as dull-as-dishwater. We get to see notable moments from the play, such as the famous balcony scene, but through a news lens, which is less epic-romance.
The screenplay for the most part is pretty whip smart with some decent humorous moments and action-set-pieces. Outside of the comedy, I was very curious how this movie would handle the tragedy aspect. Tonally, the writers do play it smart with these aspects and it makes for a really satisfying finale. Visually, the movie does have a nice look with a rich and layered production design and uses its great natural locales to give it a bigger scope and feel.

Kaitlyn Dever (Booksmart) is really great as the titular Rosaline, and her signature dry wit works perfectly for the film’s stuffy setting. Isabela Merced is dazzling as Juliet and is talented with a charm that commands all the scenes that she is in. The supporting cast, including Kyle Allen, Sean Teale, Bradley Whitford, Christopher McDonald, are all fantastic.
That being said, the movie is far from perfect. Rosaline, for all its cleverness and subversions, never strays very far from the time-tested tropes and cliches. It was a big missed opportunity that the writers never worked harder to push more boundaries without sacrificing the message or tone. Also, the second act does start to sag a bit and could have used a tighter overall focus.
Karen Maine’s spin on Rosaline (based on the novel When You Were Mine) is certainly not as trailblazing as it would like you to think. However, it has enough wit, charm and great characters that you do not really mind the more clunky elements. If you have an open mind, you will enjoy this new spin on a classic.
Rosaline will be available to stream exclusively on Hulu on October 14, 2022.
[youtube https://www.youtube.com/watch?v=DVMc3rUXW-A]
Rosaline is a smartly written re-telling of a classic with wit, charm, and some great characters.
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GVN Rating 8
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Big film nerd and TCM Obsessed. Author of The Ultimate Guide to Strange Cinema from Schiffer Publishing. Resume includes: AMC’s The Bite, Scream Magazine etc. Love all kinds of movies and television and have interviewed a wide range of actors, writers, producers and directors. I currently am a regular co-host on the podcast The Humanoids from the Deep Dive and have a second book in the works from Bear Manor.