Be Prepared to Think.

Rating: 8/10 (14 July 2002)

I like this film because it makes you think. It is in no way a standard feel good film or action flick in the traditional sense. The trailers for the film are rather misleading because none of them mention anything besides the fact that Cruz, Cruise, and Diaz are in it.
A lot of critics hated this film because of the plot. Perhaps that's why the studios didn't advertise it. However, judging from the reviews of other people on this site, this film has found an appreciative audience.
Vanilla Sky challenges the viewer to figure out what is real and what is not. Its plot is a close cousin of films like Jacobs Ladder, The Others, Mullholand Drive, Fight Club, Lost Highway, The Matrix, The Sixth Sense. All of these films play off the concept of alternate realities. If you like films that make you wonder if you're living a dream, then check out this film.
My only personal qualm with the film is that, if you take it literally, you have no reason to fear death and therefore can do horrible things to others, and to yourself, and somehow be a better person because of it. That is... IF you have enough money. I don't think this something the director or writer was purposefully trying to portray, but that's what I got out of the film, among other, less selfish things. All this means that the director didn't have a concise vision for the film.
Vanilla sky is a spooky, eerie, thought provoking film. But because of a jumbled vision, the film will not be a classic. It COULD have been better but it's not bad at all. I give it 80% out of 100%. Better than average but not A material.