If The Matrix was the digital sci-fi alternate reality film of the turn of the century, Vanilla Sky would be the slightly less impressive analogue version. Starring Tom Cruise opposite Penélope Cruz, Vanilla Sky takes on a lot of big, high concept ideas and achieves some of them pretty well and some less so.
To summarise what the film ultimately ends up being about would be pretty a pretty big spoiler, but to put it vaguely it presents us with a choice: is fake happiness better than real emotion? What if you don't even know it's fake? In the less successful philosophical avenues VS takes us down, you look into the life of a man who seemingly has it all, the wealth, the women, even the best friend, but is somehow empty inside when an accident and a rejection present him with something he cannot have.
Cruise stars alongside the other Cruz with the pair being joined by Cameron Diaz to form a confusing and passionate love triangle that is ultimately the undoing of the playboy-come-businessman as he descends into a dream like haze of reality and hallucination bleeding into one another. Cruise tends to come across well as the narcissistic, self-involved daddy's boy although most of that probably comes naturally with being Tom fucking Cruise. Cruz (who played the same role in the original Spanish version of the film Abre los ojos) plays one of her typical earlier Hollywood roles, in that she's the flirtatious and endearing dreamer. In one of the key scenes she steps out of the happy-go-lucky character in one of the more realistic reactions to a "hero" in a hollywood romantic relationship, but it is followed immediately in the next scene by a bit of character development that comes straight out of left field, but fear not, this is actually explained pretty well at the end.
Speaking of the end it's all a bit confused. The first third of the film sets up a nice bit of intrigue with prison cells, a psychologist and a mask. There are questions set up and the answers look like they'll really deliver. After this the film kind of goes off the rails a bit with the whole dream and/or mental illness concept; identities are switched up, things don't follow chronologically and things happen that just flat out don't make sense. It pretty much continues like this until the final 15-20 minutes of the film, where director Cameron Crowe seems to have painted himself into a corner. The finale of the film starts off with two characters literally stood in a moving lift with one explaining the plot to the other. It's a masterclass in how not to follow the film-maker's mantra of "Show don't tell". That said the emotional climax is pretty heavy and some harsh truths are brought to the forefront for both leads. I'm not quite sure the emotional impact outweighs the clunky approach, but it definitely compensates a great deal.
Vanilla Sky is a bit of a difficult one to rate. I enjoyed it towards the end, once things became more coherent again, but large periods of the film just felt like self indulgence on the part of the people making the film, as if they were making it for themselves and not the audience. When it's good it really is quite good, but the confusing bits are most likely to just leave you saying "Eh? What?" than the deep ponderings they were so clearly intended to induce.