25. Hoosiers 1986
Most school movie jocks are belligerent bullies. But Jimmy Chitwood (Maris Valainis) is part Larry Bird, part Rain Man, letting the swish of the basketball net do his talking. Hoops-crazed Hickory, Ind., adores him for it. His support of embattled Coach Dale (Gene Hackman) sways the town, and his skill transforms Dale from goat to genius. In the championship game, the Brylcreemed god overrules Dale's last-second strategy with three words: ''I'll make it.'' Definitely. — Jeff Labrecque

24. Rushmore 1998
For some reason, Rushmore doesn't quite feel like a high school movie. Maybe that's because director/co-writer Wes Anderson's wonderful comedy doesn't feel like any other movie ever made. But it's about school days: Just the fact that Jason Schwartzman's tirelessly enterprising Max Fischer is a student at all becomes palpably bittersweet, since he's too young to ever win Olivia Williams, the teacher of his (and anyone's) dreams. — Gregory Kirschling

23. Cooley High 1975
Written by Good Times co-creator Eric Monte and directed by Michael Schultz, this tearjerker provided the blueprint for Boyz N the Hood. In mid-'60s Chicago, geek Leroy ''Preach'' Jackson (Glynn Turman) and hoop star Richard ''Cochise'' Morris (Lawrence-Hilton Jacobs) struggle to stay out of trouble while prepping for graduation. The soundtrack, featuring G.C. Cameron's ballad ''It's So Hard to Say Goodbye to Yesterday,'' remains as beloved as the film. — Margeaux Watson

22. American Pie 1999
A frivolous teen comedy that left its mark: Jason Biggs taught us the dangers of webcam misuse (and baked-goods abuse), while the guy who'd become Harold — or was it Kumar? — popularized the term MILF. Pie was both funnier and bawdier than Porky's, though that 1981 romp gets points for Kim Cattrall's outrageous orgasm scene. But even she can't top Alyson Hannigan's perfect delivery of the line (all together now): ''This one time? At band camp?'' — Hannah Tucker

21. Grease 1978
Still the top-grossing film musical ever, Grease may look too pure to be ''pink,'' but listen to those lyrics (and watch John Travolta ogle Olivia Newton-John in ''You're the One That I Want'') and you may find yourself blushing. Beneath the karaoke-heaven soundtrack lies a story with teen pregnancy, ''pussy wagons,'' and a TV personality trying to put an aspirin in a girl's Coke. Naughty but harmless, it's just like high school should be. — Mandi Bierly