The Good, the Bad and the Ugly (Sergio Leone, 1966)
I really like Westerns in theory, but I seem to have trouble getting into them whenever I actually watch one. This is obviously one of the classics - called by some the greatest Western ever made. It's quite long (nearly three hours) and very slow, especially in the first hour, and initially I was a little bored and impatient with it. But once the story picks up and you get to know the characters better, it's fascinating, and it's got both great action (the three-way stand-off at the end is fantastic) and interesting social commentary. The three main characters are on the trail of a buried treasure during the Civil War, and while this incredibly important and divisive battle rages around them, they couldn't care less, treating it as little more than a nuisance. I don't think I've seen another film that treats the Civil War this way - it's generally regarded as such an important part of American history that no one seems willing to dare trivializing it. Of course, Leone's not American, and the film doesn't really trivialize the war, just shows it from a different perspective. The three bandits alternately align themselves with the Confederates and the Union whenever it's convenient, and none of the frontier settlers seems to much care who wins the war, as long as they profit from it. It's a very interesting take on it.
Pumpkin (Anthony Abrams & Adam Larson Broder, 2002)
I think it's time to admit that I have a problem: I am obsessed with Christina Ricci. How else can I justify watching this lame excuse for a black comedy, which is neither funny nor particularly satirical, is painfully long, meanders all over the place and totally miscasts Ricci as a perky sorority girl? I totally can't. I'm sorry. I need help.