For another '90s teen classic where a guy is way too pressed to get a girl who quite frankly enjoys her own company, there's "She's All That." Popular jock Zack Siler (Freddie Prinze Jr.) has to turn outcast artist Laney Boggs (Rachael Leigh Cook) into prom queen material to win a bet and protect his reputation. For the record, because apparently it needs to be said: Laney was beautiful with her glasses! While we don't exactly buy into the makeover trope that riddles teen movies of yesteryear, there's still a lot to enjoy in this classic, like "10 Things I Hate About You"'s Union, who steals every scene she's in.