Napoleon Dynamite...
As I understand, there was a major hype around this one a while ago. It's the typical non-typical MTV production a-la Daria, Beavis and Butthead, that has the tendency to take the most cliche teen-movie situations (first date, prom, highschool president elections) or just general teenage topics and treat them in a twisted point of view. This one especially connects with Todd Solondz's Welcome to the Dollhouse movie. Both share strong 80's aesthetics and choose to follow the classic-outcast's interactions with society, while making the whole high school deal seem surrealistic, grotesque even. Here, though, this point of view isn't taken into extreme, but rather left as a self aware comedy of nonsense, which makes for a very enjoyable (and pointless, of course) viewing.
The characters are very colorful and quite hilarious, and watching them placed together, and their different reactions, is basically what makes this movie what it is.