8. Not Another Teen Movie
A whole decade before he became Captain America, Chris Evans starred in this devastatingly funny send-up of classic high school comedies, albeit one which has been unfairly lumped in with all the other "...Movie" movies.
Not Another Teen Movie is not a film made in good taste by any means: there's an extended gag where a classroom gets showered in faeces, and Evans walks around with a banana sticking out of his ass at one point, so there's that.
And though it's easy to dismiss a film like this as another broad, gross-out parody that has no staying power whatsoever, this is absolutely the best (and smartest) of all the comedies that followed Scary Movie's lead.
Smartly picking She's All That as its primary target of mockery - a timeless "ugly duckling" story which will keep being told until the end of time - Not Another Teen Movie also keeps the topical period humour to a minimum while steering the comedy towards classic coming-of-age movies we've all seen.
And moreover, it isn't so much a mean-spirited takedown of these films as it is a loving ode to them, even while underlining their thorough absurdity, and sometimes, their rampant sexism.
Probably the smartest gags in the movie involve an extended third-act dance sequence (prompting one character to declare, "You'd never guess that everyone at this school is a professional dancer!"), and an hysterical subversion of the cliched romantic airport reconciliation, where the doe-eyed love interests get together despite it being painfully clear they're ill-suited for one another.