David Ames (Tom Cruise) lives a charmed life the ultimate golden boy. He's got looks charisma and money--lots of money. David has inherited a multimillion-dollar publishing business from his late father and he could care less about it. He has women buzzing around him like flies including one actress Julie Gianni (Cameron Diaz) who has more than a crush on him. One fateful night David meets the girl of his dreams Sofia (Penelope Cruz) and has an amazing all-nighter with her where she tells him profound things like "Every minute that passes is an opportunity to turn things around." David finally understands what it means to fall in love and to commit but then abruptly his luck runs out. In the morning David flushed with exhilaration as he leaves Sofia's apartment makes a near-fatal mistake: he gets into a car with Julie who has been following him to smooth things out with her. In one tragic moment his whole life radically changes. He desperately tries to piece things together to get Sofia back but the more he tries the stranger the circumstances become around him especially when he's accused of murder. Soon he's not sure whether what's happening to him is a dream or reality.
Cruise is a great actor when given the right material. His performances in movies such as Born on the Fourth of July and Magnolia show that Cruise has the acting chops to dig in and make it work. Unfortunately Vanilla Sky wasn't the right vehicle for him. Cruise is actually somewhat compelling as the superficial rich guy who falls in love and then deals with his tragic deformity but his performance falls apart halfway through the film as the character spirals into his own private abyss. His co-star Cruz who played the same character in the 1997 Spanish film on which Sky is based Abre Los Ojos is truly a beauty on screen but the chemistry between the two was pretty tame. Somehow Sofia's transition into the English-speaking world lacks passion. In fact the only time Sofia is truly passionate is when she yells at David in Spanish. Diaz does a serviceable job playing the stalker Julie but doesn't really have much screen time. Even the usually good Jason Lee as David's best friend seems wasted. Only Kurt Russell's supporting turn as David's prison therapist hangs together and rings true.
It's painfully obvious writer/director Cameron Crowe did not make this movie from his heart like his other films. Instead he adapted the material from Abre Los Ojos a film about the world of casual sex and young adults taking responsibility for their actions and turned it into this convoluted mess. Sky starts with some promise as Cruise's shallow playboy deals with the increasingly wacky Julie and then falls in love with the beautiful Sofia. The long night David and Sofia spend together is filled with sexual energy (more from their banter though than any real sparks between the actors) and the characters seem alive--just the stuff Crowe thrives on. Even the pain David first goes through after the accident is moving. The wonderful thing about Crowe is he can really write unbelievable dialogue. Sofia has one of the best lines to describe Julie as she watches her pine after David: "She's the saddest girl I've ever seen holding a martini glass." Yet it is clear that if Crowe doesn't feel it in his bones the movie falls flat. Once Sky moves off into the surreal halfway through Crowe loses his touch and you're left scratching your head saying "Huh?"