Chuck Bass as James Spader's A-Hole Yuppie Character in Pretty in Pink
Colorful blazers? Check. Gleeful snobbery? Check. Faaaabulous hair? Check again! Imagine Chuck Bass looking some girl up and down and declaring she "was, is, and will always be nada."

Vanessa as One of the Ferrets from Beastmaster
Nothing to see here, just a mean Vanessa joke we instantly thought of while brainstorming this list. Hopefully she could be the one who dies. (One of them dies in the movie. Spoiler alert?)

Serena as Private Benjamin in Private Benjamin!
Private Benjamin was a beautiful blonde socialite with a heart of gold and shit for brains, but when she got tricked into enlisting in the army she found a strength within herself to beat the system in some fabulous lingerie, and still have the energy to dump that two-timing piece of Eurotrash Armand Assante at the end. It's pretty much the role Serena van der Woodsen was born to play.

Dan Humphrey as Dead Poets Society's Neil
Oh my god, can you imagine Dan Humphrey as Puck? And we thought his performance in The Age of Innocence was hilarious. Plus they both liked reading and whining, and we wouldn't mind seeing Dan die in a movie, if it's never going to happen on the show.

Rufus as The Nothing in The Neverending Story
No character adjustments required! Move along now, just a mean Rufus joke we instantly (and I mean instantly) thought of while brainstorming this list.

Erik van der Woodsen as Teen Wolf!
It would explain his frequent absences and ever-changing appearance, at least. "Where's Erik?" "Oh, off teen wolf-ing again." "Ah, that explains the new hair."

Jenny as Veronica in Heathers
Veronica wanted to be popular like it was her job, and it ended up royally screwing her life up. Jenny may not have taken Blair out like Veronica and J.D. disposed of Heather, but you know deep down she wanted to.

Nelly Yuki as the Entire Cast of Revenge of the Nerds
In the cinematic translation of Nelly going to Yale while Blair settles for that one-room peasant school, NYU.

Blair Waldorf as a Female Version of Tom Cruise in Risky Business
Originally I was going to just have Blair be the Glenn Close role in Dangerous Liaisons, but decided it was too obvious and not iconic enough. Then I thought -- who could run a brothel out of her parents' house better and more fabulously than Blair Waldorf? She wouldn't be caught dead underoo dancing, but hasn't that Guitar Hero commercial ruined that scene forever, anyway? Plus, we already know she likes to have sex inside modes of transportation, so that famous scene is taken care of. That'll teach Yale not to let our girl in.

Other ideas? Blair as Robocop? Dorota as Tootsie? I know, this was obvious to me, too. Leave 'em in the comments!