Every Tom Cruise Movie Ranked From Worst To Best

Vanilla Sky is a tough film to get your head around. On the one hand, it's trippy, metaphorical execution is interesting enough to keep you invested; on the other, it's increasingly convoluted plot can be enough to drive you mad.

A perfect example of a film you have to see more than once to understand (and even then, you probably won't), Vanilla Sky stars Cruise as a cruel publisher who loses his grip on reality after a car crash purposefully caused by an enraged Cameron Diaz.

Cruise does his level best to keep things moving smoothly, and though the film's a hard one to digest, it's nonetheless one of the actor's most daring and left-field projects to date, and he deserves some props for taking the chance.