For Valentine’s Day, we’re once again looking at the wide variety of onscreen relationships: movies about ill-fated couplings, toxic partners, and unconventional romances, to help offset the sticky-sweetness of the season. Follow along here.
Vanilla Sky is not a great movie.
Featuring dorm-room philosophizing, an embarrassing Tom Cruise performance, shaggy storytelling, and the kind of cringe-inducing twee dialogue that writer/director Cameron Crowe had been flirting with his entire career yet never fully succumbed to, this English-language remake of Alejandro Amenábar’s Abre los Ojos (Open Your Eyes) is an ambitious mess that probably wouldn’t make the cut of most critics’ top 1,000 films of the 21st century.
But in depicting toxic relationships, it’s kind of a master class. And in doing so more than a decade before the #MeToo movement rightfully empowered feminists to call out harmful male behavior (while U.S. voters twice elected a misogynist convicted felon to the highest office in the land), it feels ahead of its time as a critique of masculine egotism.
At its heart, the whole film is about unhealthy bonds. From his initial interaction with a fellow human, publishing empire heir and notorious playboy David Aames (Cruise) treats everyone poorly as he puts his own interests first. On the cusp of turning 33 — one of the film’s oddly plentiful Jesus allusions; go down that rabbit hole at your own risk — this narcissist obsessively plucks gray hairs, has staffed at least one of his three magazines with attractive young women, and admits to believing he could be the one person to achieve immortality.
The karmic consequences of living forever are fitting for a man whose every connection seems on the verge of collapse. Though he appears to express some form of admiration for the lovely Julie Gianni (Cameron Diaz) after she spends the night in his luxurious Manhattan penthouse, he’s quick to dismiss her as merely a friend with benefits when his “best friend” Brian Shelby (Jason Lee) inquires about their status.
David may be generously bankrolling Brian as he writes his novel, but this patron otherwise expresses little loyalty to him. The instant David lays eyes upon dancer Sofia Serrano (Penélope Cruz), Brian’s date to David’s birthday party, he swoops in and begins flirting, barely flinching even after Brian calls him out on his behavior.
Suddenly immune to an uninvited Julie’s bedroom advances, David mysteriously enlists Sofia to help him lose his “stalker” — a bizarre shift in behavior that suggests he’s terrified of commitment to someone who clearly adores him while he hypocritically pursues a monogamous future with a woman he met minutes earlier.
Based on Sofia’s speedy acquiescence, Crowe wants viewers to believe that this meeting is one of love at first sight between both parties, and over the course of a magical, chivalrous, sex-free evening, Cruise/Cruz do an admirable job of convincing us that change is a-coming for our toothy male protagonist.
The next morning, however, David is back to his old ways. Basking in the glory of new love — unmistakably evinced by Cruise’s trademarked, gobsmacked overbite — he’s nevertheless suffering a case of blue balls, and when Julie drives up from her surveillance position at the end of the block with an offer to relieve his condition, he zips into her car and they head to her place.

Upon making this fateful decision, David deserves every ounce of pain that awaits him. As Julie pours her heart out while dangerously weaving through traffic, some viewer catharsis is achieved as she lays into him with harsh truths about his character. And despite her whiplash-inducing pivot from jilted fuck buddy to murder/suicide mastermind, there’s little to suggest Julie deserves to be treated so poorly by her would-be lover.
Though Julie’s plan is only half successful, David’s post-crash disfigurement serves as a physical manifestation of his poor decisions. Terrified of the truth, he hides behind a literal mask, falsely claiming that vanity has nothing to do with his hesitancy to show his face in public.
Arriving two years after the brilliant one-two Cruise-mystique-critiquing punch of Magnolia and Eyes Wide Shut, Vanilla Sky doesn’t quite reach those films’ levels of emotional insight. But like those superior works, Crowe’s entry also ascribes to the notion that this Cruise archetype’s most toxic relationship is with himself.
As such, it’s natural to be skeptical of David’s second chance with Sofia — namely because he simply doesn’t deserve it. Despite this new lease on life, the guy can’t even reciprocate a naked Sofia’s “I love you” in bed (while no less than Bob Dylan plays on the soundtrack!). Yet it’s his deep-rooted self-deception that truly proves his downfall.
Unable to cope with reality, David enlists the services of cryogenic suspension company Life Extension and its lucid dream option so that he can artificially be with Sofia forever. But even with this god-like advantage, David’s self-absorption is so extreme that — with the help of a software glitch — he soon turns his perfect fantasy into a nightmare.
The resulting journey of self-realization plays like It’s a Wonderful Life on acid, and though a transformation of sorts awaits on the other side, David’s predictable behavior when happiness is thrust upon him makes it difficult to buy Vanilla Sky’s positive concluding note. But who knows? Perhaps this walking cautionary tale will do better in Vanilla Sky 2: Electric Boogaloo. Yet like the real-life Cruise/Cruz romance that arose from this production, David’s purported rehabilitation seems unlikely to last.
“Vanilla Sky” is streaming on Hoopla and available for digital rental or purchase.