Vanilla Sky was definitely not the movie Cameron Crowe fans were expecting to see when they filed into theaters in December of 2001—especially not with Crowe's Jerry Maguire leading man Tom Cruise looming large on the poster. Instead of a feelgood romance or a fun coming-of-age story, they got a moody, elliptical remake of a hit Spanish film. A feckless playboy (Cruise) suffers near-death and disfigurement after his relationship with his new girlfriend (Penélope Cruz) plunges his ex-lover (Cameron Diaz) into homicidal obsession. He plunges into depression, has his face surgically restored, and then his life really starts to go haywire.
Ultimately, viewers are told that much of what they've seen is a lucid dream in Cruise's brain, which has been held in cryonic stasis for more than 100 years, and that the more troubling elements of the narrative are the result of a glitch. He's given the choice to either reboot the dream or exit it once and for all by jumping off a building and being brought back to life. He jumps—and the last shot is of Cruise's character opening his eyes, starting his life over again.
There are lots of interpretations for all this, some of which were supplied by Crowe himself in the commentary track for the DVD—but the correct one might just be accepting what you see onscreen as the actual events of the story. Crowe seemed to lean that direction while talking with Film School Rejects about Vanilla Sky's unused alternate ending:
"You want people to understand what you're going for, so the question is, looking at both endings: Did the pendulum swing too much in the direction of us explaining stuff? I think it did. The original ending was more open-ended, a little less explained."
From Looper.com
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