Rosaline offers an audacious alternative to Shakespeare’s Romeo And Juliet

If the name Rosaline rings a bell, it’s because she’s the mentioned-but-never-seen girlfriend Romeo was dating right before falling for his one true love in William Shakespeare’s Romeo And Juliet. Yet in director Karen Maine’s feature Rosaline, the character once regarded as a footnote becomes the lead, guiding a hilariously irreverent and empowering re-fashioning of that tale of woe. Crafting a comedy from the perspective of the Bard’s minor characters isn’t exactly new, as Tom Stoppard’s Rosencrantz And Guildenstern Are Dead did the same with Hamlet, but the innovative idea is reinvigorated with witty dialogue, a solid ensemble and astute direction.

Though others her age wed for money, status and land, Rosaline Capulet (Kaitlyn Dever) is determined to marry for love, going so far as to scare off potential suitors for an arranged marriage. Her doting dad (Bradley Whitford) thinks he’s found the perfect match to tame Rosaline’s tempestuous spirit: hunky heartthrob Dario (Sean Teale), who’s returned to visit his parents while on a short leave from military service. Yet Rosaline’s heart already belongs to another: handsome himbo Romeo Montague (Kyle Allen). Their families’ years-long feud prevents their illicit romance from going further than sneaking love letters while passing in the street or stealing embraces on her balcony under the cover of night.

Rosaline’s world turns upside down upon the arrival of her estranged cousin Juliet (Isabela Merced), who’s also fallen for an irresistible, achingly romantic young man. It’s Romeo of course, and he’s infatuated with Juliet. So much so that his laser focus on her doesn’t give him any time to break it off with Rosaline, whose lovelorn heart still pines for him. Being the clever, resourceful mind that she is, Rosaline plots to break up the star-crossed lovers. She even enlists the help of gay bestie Paris (Spencer Stevenson) to escalate her plan. But her efforts take unexpected turns, leaving her frequently in the company of Dario as they find themselves in foreign territory—both literally and figuratively.

Adapting screenwriters Scott Neustadter and Michael H. Weber have made shrewd, intelligent changes from Rebecca Serle’s book When You Were Mine, on which the film is based, changing the setting and time period from modern day Southern California to Renaissance era Italy. This shift not only provides the proper basis for many of the jokes and comedic hijinks, it smartly disposes of modern trappings, adding a timelessness to the picture and justifying stoner Steve the Courier’s (­­­Nico Hiraga) blessed existence. They trim the fat, doing away with more than one best friend for Rosaline. Integrating references to Shakespeare’s original characters and period-specific scenarios keeps the narrative cleanly constructed.

However, not all the changes are for the better. Altering Rosaline and Juliet’s interpersonal relationship, making Juliet less of an antagonist and more of a naïve rube, coupled with Rosaline’s not-mean-spirited-enough scheme, fails to give the second act a strong motor. While it wouldn’t be in the film’s best interest to become a reductive story about two women fighting over one man, Rosaline and Juliet’s friendship and eventual betrayal don’t carry much weight—at least until the third act, when Rosaline’s inevitable redemption surfaces.

Maine and her cadre of craftspeople gift her follow-up to Yes, God, Yes with a lavish, tactile feel typically missing from the bland, flat look of streaming films of its ilk (like Netflix’s Persuasion). Cinematographer Laurie Rose harnesses the power of soft, natural light to highlight characters’ pure intentions. Editor Jennifer Lee’s sense of montage delights, as she cuts with precision to heighten comedic effect. The soundtrack complements the equally anachronistic modern dialogue, pulling influence from A Knight’s Tale in track selection and Bridgerton in period-stylized covers. Maine, along with composers Drum & Lace and Ian Hultquist, even drop a winking nod to Clueless for kicks and giggles.

Dever is as excellent as ever as the acerbic, quick-witted, jilted ex. She coaxes the hilariousness and heartbreak out of each scene with ease and authenticity. While Dario’s internality isn’t explored much, Teale gives him depth and dimension, with glints of inspiration from Cary Elwes in The Princess Bride and Heath Ledger in 10 Things I Hate About You. Minnie Driver is a standout in the supporting cast as Rosaline’s caring-but-exasperated Nurse Janet, channeling John Cleese’s dry British wit in her multi-faceted work.

Rosaline’s impactful arc is both sincere and self-aware as it promotes its protagonist from the wings to center stage. Though not entirely perfect, this inventive picture’s flaws feel forgivable, if not downright charming. Perhaps serving to inspire a younger generation to think outside the box when it comes to writing, or in this case re-writing inspired fiction, Karen Maine’s film is lovable enough not to discard.