6. Ricky Lipman - Not Another Teen Movie
Why He's Awesome: Ricky Lipman is constantly in the service of the film's nerdy protagonist, Janey Briggs, recording mix-tapes for her and writing lovesick poetry that he reads out in class, proving to be a hilarious satire on the "friend zoned" buddy of the girl, who is in fact much better suited for her than the guy she ends up with.
How He Got Shafted: This satire results in a hilarious climax which completely gives Ricky the shaft; he gets his by a bus on the way to the airport to stop Janey from heading to France for art school, and is beaten there by Jake (Chris Evans), who professes his love for her and gets the girl. Ricky shows up moments later, filthy and bloody from his accident, causing nobody to believe his story or applaud his efforts to win Janey over. Poor guy, but at least he beats that other dude to the slow clap (even if he gets mercilessly beaten for it).