21. Sky Captain and the World of Tomorrow - I was always alarmed by how many people trashed this movie without bothering to really watch it. I was also surprised by the lack of comprehension as to what the purpose and mode of the story was. This is an old-fashioned, innocent, wide-eyed adventure noir swiped directly from 40's comic books. The dialogue is deliberately cheesy, but that's exactly what it's supposed to be... The aesthetics are spot on and incredibly gorgeous. Really, and to think that a couple years later everyone acted as though 300 was a modern marvel. I agree with Roger Ebert, i think this film captured exactly what it set out to and personally, i appreciated that.
22. Bandits - It's one of those decent movies that's largely forgettable. For some reason, i really enjoyed the simplicity of the crimes and the neurotic chemistry between Billy Bob Thornton, Cate Blanchett, and Bruce Willis. It marks one of the only instances in which Thornton can be referred to as adorable and a convict love triangle can be called charming. Really and truly.
23. Cruel Intentions - I love Les Liaisons Dangereuses as a French novel. Therefore, a teenage, prep school, sex romp version should somehow compute as a complete bastardization of classic literature, right? Oh so wrong. This is one of those movies that i wanted to resist but wound up completely accepting. Sarah Michelle Gellar and Ryan Phillippe as super manipulative popular kids? They give the Gossip Girl kids a run for their money. Despite all the tacky scenes and deliberate shock value, i will watch this whenever i'm given the opportunity. Plus, the soundtrack is killer. I mean, seriously, they even used one of my favorite songs in the trailer.
24. Freaky Friday (2003) / The Parent Trap (1998) - I'm counting these two Disney/Lohan remakes as being essentially one guilty pleasure because, well, they're basically the same movie: a silly gently bent gimmick about family togetherness. It's fairly taboo to enjoy Lindsay Lohan fare these days (the exception being Mean Girls), especially if you're a 20-something film aficionado. But over the years i've seen both of these movies more times than i'd care to reveal (thanks in part to younger relatives, but they're also both great for when you're stuck in bed or on the couch sick) and every time they leave me perfectly happy.
25. Velvet Goldmine - This movie is incredibly beautiful, but so piecey. Director Todd Haynes has some issues with cohesion, i would say. There are huge segments that don't work at all, it's too long, and parts are just laughable. I have seen this movie several times in the company of almost everyone, and i'd say 60% of audiences have finished the movie feeling somehow dirty. It's a rough, unflinching, and often mythologized vision of the glam rock era. For every one thing wrong there's two that are right, and for every time i view it and question my taste, there are two viewings where i am suitably impressed. The costumes and soundtrack alone are completely brilliant. Jonathan Rhys-Myers looks his best in make-up and shiny clothing. True story.
Honorable Mentions: The Island, Constantine, Nanny McPhee, etc.