When the ahead-of-its-time film Vanilla Sky was initially released, people didn’t really know what to make of it. After all, on paper, it certainly seemed like a winner. You had writer/director Cameron Crowe, hot off his Oscar-winning, career highpoint, signature film Almost Famous. He reunites with star Tom Cruise for their follow-up to the critically acclaimed, award-winning, feel-good, guy-friendly rom-com Jerry Maguire. What could go wrong?

Well, as it turns out, a lot. Coming off a marriage that disintegrated during the endless shooting of Stanley Kubrick’s final film, Eyes Wide Shut, Cruise was in a bit of a “dark” period that also included an excellent turn as the misogynistic “motivational” speaker in the somewhat underrated Paul Thomas Anderson flick Magnolia. That would continue with the dystopian sci-fi opus Minority Report and the brazen hitman role in Michael Mann’s likewise underappreciated Collateral.

Between these atypical roles and Cruise’s later oddball outbursts on TV, railing against psychiatry and jumping up and down on Oprah Winfrey’s couch declaring his love for actress Katie Holmes, the public didn’t quite know what to do with him. This resulted in a series of films that didn’t quite perform as expected at the box office, eventually leading Cruise to fall back on his action movie laurels and stick with the likes of the Mission Impossible series.

It’s too bad, as Cruise did some of his strongest work in this period, with Vanilla Sky being a decided highlight. Though the film received decidedly mixed reviews at the time, it performed well enough at the box office, taking in over $203 million on a $68 million budget- not too shabby for what amounted to the blockbuster equivalent of an arthouse flick.

Which makes perfect sense when you realize that Vanilla Sky is actually a remake of the 1997 Spanish movie Open Your Eyes from filmmaker Alejandro Amenábar, who gave his blessing to the remake and even visited the set. Though Crowe’s remake lacks the undeniable dream-like quality of its predecessor, it more than makes up for it in its visual grandeur and typically fantastic soundtrack. The soundtrack befits a man who used to cover music for Rolling Stone from when he was a mere teenager, itself the subject of his previous film, Almost Famous.

The Music

In some ways, the Vanilla Sky soundtrack is even better than the admittedly excellent Famous one, running the gamut from the then-burgeoning EDM movement, with tracks by Underworld and The Chemical Brothers to excellent deep cuts from the likes of Bob Dylan, Todd Rundgren and even The Monkees.

In addition, the film boasts a lovely score from Crowe’s then-wife Nancy Wilson, best-known as a member of the classic rock mainstays Heart, plus a title track written expressly for the film by none other than Paul McCartney, who received an Oscar nomination for his song. It was also the film which introduced me to the excellent Icelandic ambient rock group Sigur Rós, who are well-worth seeking out if you’re not familiar.

The Cast

Also worth a mention is the excellent cast, which features some actors you might not recall being in it, or simply weren’t familiar with at the time. In addition to Cruise and main co-stars Penélope Cruz and an arguably never-better Cameron Diaz (gotta be this film or Being John Malkovich), you have Kevin Smith mainstay Jason Lee, pre-My Name is Earl; the legendary Kurt Russell; an incredibly-young looking Noah Taylor, long before Game of Thrones; and a pre-Harry Potter Timothy Spall.

What’s more, you have brief-but-memorable turns from Tilda Swinton, personal fave Alicia Witt (Urban Legend), a young Michael Shannon, a pre-Big Bang Theory Johnny Galecki, talk show host Conan O’Brien, and various supermodels of the day- including a pre-Banshee Ivana Miličević and Shalom Harlow.

Plus, there’s an appearance by no less than Steven Spielberg, who was visiting the set to talk with Cruise about their upcoming project together, Minority Report, and gifted Crowe with a cameo in which he calls Cruise’s character a “son of a bitch!” Crowe would return the favor with a cameo of his own in Report. Also worth a mention is that then-future director Catherine Hardwicke, best-known for Twilight, served as the production designer on the film.

The Story

Vanilla Sky follows protagonist David Ames (Cruise), a self-involved publishing magnate, who inherited his father’s empire at a decidedly young age. Receiving a controlling share in the company, it resulted in quite a bit of resentment from the older board members he has to report to. We meet David on the morning of his 33rd birthday and get a glimpse at his playboy lifestyle, which includes a supposedly no-string-attached “relationship” with Julie (Diaz) and palling around with best bud Brian (Lee, at his most likable).

When Brian shows up at David’s birthday party with the lovely Sofia (Cruz), David wastes no time in moving in on her, much to Brian’s chagrin. After falling deeply for her over the course of one night, David makes the mistake of getting into the car with an unhinged Julie, who has followed him there and stalked him throughout the previous evening’s festivities.

After unloading on him big-time about his treatment of her, she promptly wrecks the car, killing herself and seriously injuring David, in particular disfiguring his face. From there, David begins a downward spiral that only gets weirder and weirder as the film goes on, until David isn’t quite sure what is or isn’t real- the same of which could be said for viewers.

Fave Quotes

The film is filled to the brim with great quotes and, for the most part, steadfastly avoids the sort of treacly declarations that turned off certain viewers- think the likes of “You complete me” and “You had me at hello.” Jason Lee in particular has some great ones, acting as a sort of surrogate for those of us guys who aren’t fortunate enough to look like Tom Cruise, and who know the pain of having a friend that has snatched a girl out from under them- and not for the first time.

Here are some of my favorites:

  • Brian, to David: “Just remember: the sweet is never as sweet without the sour- and I know the sour.”
  • Sofia, to David: “Every passing minute is another chance to turn it all around.”
  • Sofia, to David: “I’ll tell you in another life… when we are both cats.” (Reportedly, it’s something Cruz actually said to Crowe at one point, which just makes it all the greater.)
  • David, to Sofia: “Look at us. I’m frozen, and you’re dead, and I love you.”
    Sofia: “It’s a problem.”
  • Brian, to David: “You will never know the exquisite pain of the guy who goes home alone.”
  • David, to his psychiatrist: “If I talk, you’ll just think I’m crazy.”
    Dr. McCabe: “With all the possible respect I can offer a man wearing a latex mask and spouting conspiracy theories, David, believe me, you’ve crossed that bridge.”
  • David, after a nearly having a car crash: “We almost died.”
    Brian: “I know. My own death was right there in front of me, and you know what happened? YOUR life flashed before me eyes.”
    David: “How was it?”
    Brian: “Almost worth dying for.”
  • Dr. McCabe: “I’m real! I’m… I’m… mortality as home entertainment? This CANNOT be the future. Can it? CAN IT?”
  • David, to Sofia: “I like your life.”
    Sofia: “Well, it’s mine, and you can’t have it.”
  • Sofia, to David: “What’s your nickname?”
    David, hesitating: “Citizen Dildo.”
    Sofia: “Hmm. You are not staying over.”
  • Thomas, to David: “The last time we were together, you were in a coma, and you were very fucking rude to me. You didn’t say a WORD.”
  • David, to Dr. McCabe: “Doc, once you’ve been driven off a bridge at 80 miles an hour, somehow you don’t invite happiness in without a full body search.”
  • Julie, to David: “If I wasn’t me, I’d buy my album.”
    David: “Well, you know, if you can just reach ONE person.”
  • Dr. McCabe, summing up his life to date: “My favorite Beatle was once John. Now, it’s Paul.”
    David: “I always liked George.”
  • Sofia, upon seeing Pete Townsend’s smashed guitar at David’s: “So this is what’s become of rock ‘n’ roll- a smashed guitar in a glass case displayed on some rich guy’s wall!”


Though not quite as surreal as the original, the film does get better and better as it goes on, and features a much-more elaborate puzzle than found in Open Your Eyes with lots of clever “clues” and things to decipher. My personal faves: the chalkboard and David’s X-rays. Check out the cool theories on what is “really” happening in the film, as well as a list of the various clues found within the film here.

As such, though certainly not without precedence in other similar type movies and shows- “Twin Peaks” certainly leaps to mind- Vanilla Sky undeniably pre-configures many of the later “freeze frame”-friendly offerings found in the likes of Lost and even Pretty Little Liars. The film has a plot line that likely influenced a lot of the “virtual reality” films and TV shows that followed, notably Black Mirror (especially the episode “San Jacinto”).

Despite the influence, Vanilla Sky received mixed reviews at the time, however I’ve always liked the film and, as we all know, sometimes it takes a hot minute for a film to be appreciated like it should be. As such, this is one ripe for rediscovery, for sure. Vanilla Sky is undeniably Crowe’s most experimental film, and the one which most rewards multiple viewings. Though I do love me some Almost Famous.

Alas, after the critical drubbing, he soon returned to more familiar waters with films like Elizabethtown, We Bought a Zoo, and Aloha, with unfortunately diminishing results, making one wish Crowe would throw caution to the wind and do something along these lines once again. Especially with the current climate being much more welcoming to such things these days. (Ditto Cruise.)

Who knows? In light of the “safe” choices Crowe has made as of late, he might decide to do a low-budget indie flick that takes him back to his roots again. I’ve learned to never count anyone out- they might just surprise you. Much like Vanilla Sky did a lot of people at the time. Check it out- it’s a total cult classic, and an A+ in my book.

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