Great humor, excellent cast... and more than a bit disturbing.

Rating: 9/10 (12 December 2001)

This is a very trippy movie, and the less you know about the plot going into the theater, the stronger it's effect will be. It's one of those Sixth Sense/ Usual Suspects/ Devil's Advocate "what-the-heck-is-going-on" types. The difference is, Vanilla Sky doesn't just throw out clues as to what's going on... it throws out red herrings, too. And then --just to keep you questioning what you see even more-- tells the majority of the story in flashbacks & dream sequences.
Don't be surprised if Cameron Diaz ends up getting an Oscar nomination for her role as "the saddest girl ever to hold a martini." Aside from Being John Malkovich, this is her best role yet.
Tom Cruise's performance reminded me strongly of his role in Jerry Maguire (another Cameron Crowe movie). His character is not used to caring for anyone but himself, and once again his self-centered lifestyle ends up inflicting serious emotional damage to those who love him. Instead of yelling "show me the money", this time he's yelling something else... but telling what it is would ruin the surprise. ;0)
Lots of comedy and witty dialogue throughout the movie, much more than you would expect from seeing the trailers. Jason Lee seemed to get the bulk of the funny bits, but Cruise gets in his share of memorable zingers, too.
I gave it a 9, because I haven't seen a movie this good for several months, but it wasn't quite perfect. The plot seemed to drag on unnecessarily just a little near the end (teasing the audience before the conclusion, perhaps?), and that kept me from gracing it with a 10.