A warning - I'm going to discuss the ending of this film, and pretty much everything in it. I wouldn't be able to say much about it if I didn't. It may spoil your enjoyment of the movie
Vanilla Sky is probably the film I would make if films I made were anything like the roleplaying adventures I run. That is to say the plot falls into the same category as The Matrix, Exiztence, The Truman Show and Dark City while the flm isn't quite sci-fi... Well, OK the film is sci fi, most of it happens while Tom Cruise is in cryogenic sleep (and they didn't do my cryogenic "Icy dead people" joke...), but the viewer doesn't know that - at least not at first.
Frankly the first time cryogenics was alluded it was clear that was what was going on. I happened to guess exactly the point where the cryogenic sleep started wrongly - but it didn't matter that much. There is a story tied in with all this, but frankly it isn't too interesting an can be summed up by saying Spoilt Rich Kid learns absolutely nothing, while shagging two cute women.
And thats it. The women (Cameron Diaz and Penelope Cruz) are really very cute. Tome Cruise acts well. Timothy Spall is in it, and thats always a good sign, even if his london accent isnt quite as good as his brummy one. The film is engaging, but the pacing isn't great - it lags a little, especially during the expositiory scenes.
The thing is, it isn't a bad film, its quite enjoyable to watch, passes the time well. There isn't anything special about it, but that isn't a bad thing in and of itself. 3.5 icy dead people out of a possible 5 methinks.