I had low expectations walking into this film, as I think Tom Cruise is a bad actor and Cameron Crowe is a bad writer. Everything they do is so obvious, so forced, and so unnatural. For their first post-Jerry Maguire collaboration, they chose to adapt Alejandro Amenábar's labored twist-ending Spanish movie Open Your Eyes. Crowe pads Amenábar's original story with the witty, clever-clever dialogue he so likes to write, which nobody ever says in real life. To make matters worse, whenever Crowe actually does coin a catchy phrase, he can't leave it alone - he has to repeat it over and over, like a guy telling the same joke at a party. ("That is the saddest woman to ever hold a martini", "We'll meet in another life, when we are both cats", etc.)
Meanwhile, Tom Cruise plays yet another filthy rich ladies' man with a hot car, a cool job, and everything going for him. That is, until the day he dumps his sex partner (Cameron Diaz, good but wasted) for the exotic Penélope Cruz. Diaz goes nuts and takes Cruise on a joyride over a bridge and smack into a brick wall. She dies in the accident; his beautiful face becomes disfigured. And for a little while, Vanilla Sky is interesting. Cruise Elephant-Mans himself around Manhattan with believable-looking scar makeup that distorts his face so that he actually has to act a little. Unfortunately, the story then takes a left turn into, you know, that zone where things are not quite what they seem, and the third act gets bogged down in unwelcome sci fi hogwash.
This is the A.I. of psychological thrillers: there are some good moments, and deep down the story has some interesting ideas, but the film as a whole is overstuffed and preposterous.