In 2025, Vanilla Sky just doesn't hold up. The women in the story are such flat objects, it's hard to watch it without eye roll after eye roll. The whole thing seems to think it's clever & it very much isn't. It resorts to very lazily explaining absolutely everything in great detail right at the end all deus ex machina-like. It seems like Vanilla Sky is a little time capsule filled with everything bad from the 90's. Blech. & also fuck Tom Cruise.