The Lost, Weird Art of Vanilla Sky

Introducing Endless Mode: A New Games & Anime Site from Paste

Read our announcement | See the 10 Best Games of 2025 (So Far)

Last year marked the 20th anniversary of Cameron Crowe’s seminal film, Vanilla Sky, a film I watched and then rewatched for the first time this month. My viewing of the film came during a dire time in my life, early in February when I was still feeling jaded by the year’s recent Sundance output. I had mostly been doing rewatches of films that I loved, or first watches that were either flat-out bad or not quite exhilarating. Everything changed for me after watching Vanilla Sky, a movie that, ironically, was adapted from a Spanish film that played at the 1998 Sundance Film Festival.

I feel like it’s possible that everyone is born implanted with a loose cognizance of Vanilla Sky, because it feels like I have been aware of the film for most of my life. The movie has certainly held a weird, nagging little niche in my mind since around middle or high school; that image of a wistful Tom Cruise staring off into the distance flanked on all sides by a picturesque, Mac screensaver background, his eyes following me as I downloaded songs from the soundtrack off of Limewire. But I never really knew what Vanilla Sky was about (what a treat for me, then, to finally witness at the ripe old age of 27). I knew it was a film that maintained something of an odd reputation over the years, and that Crowe infamously freaked it with the track list. I also knew that it was a science-fiction film, even if, as I watched it, I struggled to understand how it fell into that genre before I arrived at the final act. Simply put, they don’t make them like this anymore.

Most Popular

Having now seen Vanilla Sky, it’s a movie that I don’t think could ever truly disappear from the cultural consciousness even if the creators desperately tried to remove all traces of the thing. I firmly believe that if the world ended tomorrow, Vanilla Sky would still persist, like a dream held tightly in the back of one’s mind that the dreamer can no longer discern from reality or memory. Or, perhaps, even more appropriately, like the intrusive vestiges of David Aames’ (Cruise) former life that antagonize him and turn the lucid dream that he chose to embark upon into a nightmare. This is after falling in love with Penélope Cruz, after his quasi-lover Julie Gianni (Cameron Diaz) attempted to commit murder-suicide with him in her car and disfigured his beautiful face, after having committed suicide, and after being cryogenically frozen—by which point the movie had already turned into 10 different movies that reveal themselves like Russian nesting dolls across the narrative.

I was only six when it came out, but I’m positive that I’m not the first person to watch or revisit Vanilla Sky in the past few years and come away with a more acute feeling than ever that things—in the film industry, but also everywhere—are worse now. It’s a film that could only have been made at the turn of the millennium: That post-Matrix technological and existential fixation with finding oneself trapped in an artificial world, during a time when Tom Cruise was still at the top of his game and eager to make dramatic movies with auteurs (though, at this point the Mission: Impossible domino had already been struck down), when Jason Lee and Cameron Diaz were still sought-after cinema regulars and, of course, when a mainstream, Hollywood movie as insane as this could have been made with any budget behind it at all. I hate to be the kind of person who says “watching this piece of art is like being high” while having watched it stone-cold sober. But watching Vanilla Sky is truly like being high and having your high mutate from euphoria, to hilarity, to paranoia, to fear, to calm fatigue, right before you finally nod off into a deep and blissful sleep.

For those unfamiliar, Vanilla Sky follows Cruise’s David Aames: Wealthy heir to his late father’s publishing company, which he struggles for ownership of alongside a board of shareholders he refers to derogatorily as “The Seven Dwarves.” On the side, he has a not-quite-romantic but very much sexual relationship with a woman named Julie Gianni (Diaz), who views their relationship as both very sexual and, unbeknownst to David, very romantic. At a party, David’s best friend Brian Shelby (Lee) introduces him to Sofia Serrano (Penélope Cruz), who David quickly falls for—much to the chagrin of Julie. Scorned by David and, apparently, deeply unstable, Julie offers David a ride to work the next day, having followed him from his party to Sofia’s apartment where he had spent the night. After espousing an absurd monologue—in which Diaz has to utter the sentence “I swallowed your cum, that means something” with the kind of complete and total sincerity that got her nominated for numerous awards that year—Julie intentionally loses control of the vehicle and crashes the car. Julie is killed in the crash, David is left permanently disfigured and, suddenly, he must now navigate through life as a shudder weird and ugly person while he develops an increasingly passionate romance with Sofia.

Having already taken a small handful of surprising detours by this point, Vanilla Sky only becomes far more deranged. From the beginning, there are short sequences interspersed throughout which signify that the life David leads in New York, the life we were introduced to, is actually a flashback. In present day, an uncanny, silicone-masked David dons prison attire and is interrogated on a murder charge by Kurt Russell. Thus, we’re aware that the narrative has to lead us to some big reveal that David has or has not been framed for murder, right? Perhaps a trial scene is in order? No, that is indeed not the case. Far from it, actually. Despite the fact that the film is over 20 years old, I am reluctant to dig too far into the arc’s trajectory than I already have, and the hard-turn revelations one must weather while watching, because it was such a wonderful journey for me to experience being totally ignorant of the plot—let alone the film’s ridiculous and glorious final act, which left me dumbstruck as to how I had gotten there from where the film began.

There are ludicrously edited montage sequence that elicit belly laughs, like the one in which David, post-face-mangling, gets plastered in a club out of spite; lines of corny dialogue conveyed with the type of cinematic sincerity that is quickly fading into obsolescence, like Lee’s oft-recurring one about life being about “the sour and the sweet.” Of course, there are the infamous pop-rock needle drops utilized with a devil-may-care attitude from a director who had just recently won an Oscar for his acclaimed film about rock music journalism. And then there’s Cruise’s performance, which has been described as “playing himself” (I don’t really know what that’s supposed to mean) or, as the San Francisco Chronicle negatively put it, “Cruise’s vein-popping, running-the-marathon performance.” While Cruise is certainly not mining the depths he clearly had in Magnolia or Eyes Wide Shut, there is a comic urgency to his portrayal of Aames that is made all the funnier upon remembering that the film is something of a vanity project.

Though a remake of the Spanish film Abre los ojos (Open Your Eyes), one that takes everything from the original—including Penélope Cruz—except the depth, it’s hard to not view Vanilla Sky as irrefutably superior due to the reason it was made. The fact that Vanilla Sky operates as a narrative and visual carbon copy of Open Your Eyes does not negate the fact that it exists as a curious symbol of Cruise’s narcissism. It’s something that has endured and become far more crucial to Cruise’s celebrity persona as the years have gone on, and becomes far more compelling to consider in context with the plot of the film and the disfigured character that he once portrayed.

Cruise optioned the rights to a remake of Open Your Eyes immediately upon seeing it at the 1998 Sundance Film Festival, then enticed director Cameron Crowe on board as director based on their previous collaboration on Jerry Maguire. Vanilla Sky is, thus, unique from the original because of Cruise’s involvement and what the film can be interpreted as meaning to him: A movie about a man preoccupied with his image, with his mortality and the fruitless quest for eternal youth. The film marks an interesting dividing line in Cruise’s career, one of the last of a handful of roles between 2001 and 2006 before the actor would leave his multifaceted dramatic work behind for the safety of action blockbusters. Maybe the strange self-obsession of Vanilla Sky saw Cruise revealing more of his true self on screen than he ever wanted to, or ever would again.

Vanilla Sky was a financial success but a critical mixed bag. However, it has garnered a cult following over the years, perhaps due to increased fatigue over the progressively unimaginative neo-Hollywood apparatus. I’m happy to now join the leagues of “Sky Heads,” as a fan of bizarre, bombastic films that take strange stylistic chances and alienate critics like myself. Perhaps the recent reappraisal of Vanilla Sky is truly just a signifier of the way the industry has taken such a depressingly creative downturn, forcing audiences to look back on the bizarre dregs of yesteryear with the sort of rosy-eyed nostalgia that created the very nostalgia circlejerk of today. It’s also an intriguing relic when one takes a look at the state of the modern vanity project. Adrian Brody’s recent low-fi Clean, while wonderfully awful, barely made a blip. On the other end of the vanity spectrum, passion projects like Francis Ford Coppola’s Megalopolis cannot come to fruition through normal industry channels: Coppola has had to finance the entire thing himself.

As a remake itself, Vanilla Sky is not quite exempt from being another cog in the machine which has birthed the current state of the American film industry. Still, it remains a totem of a Hollywood that no longer exists, one where even a remake could be a swinging-for-the-fences concoction of wide-eyed auteurism, celebrity egotism and a double-dose needle drop of “One of Us” by Joan Osborne.

Brianna Zigler is an entertainment writer based in middle-of-nowhere Massachusetts. Her work has appeared at Little White Lies, Film School Rejects, Thrillist, Bright Wall/Dark Room and more, and she writes a bi-monthly newsletter called That’s Weird. You can follow her on Twitter, where she likes to engage in stimulating discussions on films like Movie 43, Clifford, and Watchmen.