6. Never Been Kissed (1999)
If you look past the ridiculous slapstick moments (I think Drew Barrymore runs into a door at least twice in this film), you start to feel for her spaz of a character, a reporter who goes undercover at a high school to find a story, despite having been an outcast back in her day. Performances by David Arquette, Molly Shannon, John C. Reilly, Jessica Alba and James Franco keep it entertaining, although once again Michael Vartan seems to have been cast simply because he looks dateable.

5. Billy Madison (1995)
Arguably Adam Sandler's funniest movie next to The Wedding Singer, albeit the one where he truly earned his reputation for childish humor. Of course, that's because he plays a 20-something man-child who failed every class he ever took, and his having to go back and take 1st through 12th grades all over again doesn't help matters. Don't listen to what "civilized society" tells you, watching Sandler peg kids with dodgeballs is just as funny as when Peyton Manning did it on SNL years later.

4. Hiding Out (1987)
Jon Cryer is a bearded, nearly-30 stockbroker who testifies against the mob, but when they start gunning for him, he escapes police custody and hides out at his younger cousin's high school, adopting the clever alias Maxwell House...er, Hauser and creepily hooking up with a high school girl. The beard and bad hair actually make the 22-year-old Cryer look believably grown-up -- possibly more grown-up than he does now -- but the minute he shaves them off he goes back to looking like Duckie.

3. Strangers With Candy (2005)
Amy Sedaris uglies herself up once again to play Jerri Blank, the 46-year-old junkie whore who comes back home to finish high school and seal the deal with whatever guy or girl catches her eye. Stephen Colbert steals every scene he's in as a closeted teacher, and if you like the 2-hour movie, you can go back and watch the 20-odd hours of the TV series that spawned it. (It's actually even funnier.)

2. Back to School (1986)
Before Rodney Dangerfield squandered the appeal he gained from Caddyshack in such kiddie fare as Rover Dangerfield and Ladybugs, he squeezed out one perfect film. As Thornton Mellon, Tall & Fat retail chain magnate, Dangerfield happily joins his son at college after his marriage falls apart, and enjoys throwing his money and weight around, impressing or disappointing his professors (including Sam Kinison) in the process. Also, Robert Downey, Jr. plays his first crazy person.

1. Plain Clothes (1988)
If Hiding Out is not very well-known, then Plain Clothes is just plain obscure. Probably because instead of starring 1980s legend Jon Cryer, it stars Arliss Howard, a man with a long career, but someone who was last seen making a guest appearance on Medium, for what that's worth. Still, Howard rocks his monotone delivery as an undercover cop whose younger brother is arrested for murdering his teacher. When he goes undercover at the school (backed up by Wes Anderson regular Seymour Cassel), he finds more than he bargained for in one hot English teacher (Suzy Amis) and a motley crew of teacher-suspects, including George Wendt, Abe Vigoda, Robert Stack and Harry Shearer. Worth it just for the vulgar-yet-erotic seduction poem Howard chooses to read in English class.