by Patrick Bromley
1. The Last American Virgin (1982) I've written about this one before, but it just came up in the comments with a reader and actually inspired this list. There is a lot about this movie (Cannon Films' attempt at bringing the Israeli Lemon Popsicle series to the U.S.) that is terrible -- it feels like a foreigner's interpretation of American teen sex comedies like Porky's. But then there are also weird scenes of ugly truth, like when the boys visit a prostitute and all end up with crabs, or the incredibly harsh and honest ending. No other teen movie ends like this one, and that's why those of us who still talk about it (there are a few of us) are talking about it. For all its stupidity, The Last American Virgin is one of the few movies that gets what it feels like to be a teenager right, if only for a moment.
The Night Before (1988) Thom Eberhardt's follow-up to the great Night of the Comet is another inversion of the familiar teen movie tropes. Rather than have a teen movie that gets interrupted by the apocalypse, Eberhardt plays it straight...almost. It's a standard nerdy guy (Keanu Reeves) gets date with spoiled princess (Lori Loughlin) to go to the prom story. Only we never see the prom. And the nerdy guy blacks out and has amnesia. And the spoiled princess gets sold to a pimp. The movie walks a weird line between traditional teen movie hijinx and genuine sleaze, but it's a fascinating experiment. Plus Keanu Reeves is really sweet and goofy, something he wouldn't get to be again until The Watcher.
3. How I Got Into College (1989) Having already covered the horrors of high school and what to do with the summer after graduation, the third movie in Savage Steve Holland's teen trilogy (following the great Better Off Dead and the less-great One Crazy Summer) moves its attention to higher education. The movie is missing one very important element: John Cusack. His replacement, Corey Parker, is no replacement. But it features a lot of the same absurdist humor as his first two movies and takes the lives and concerns of its teenage protagonists very seriously. Lara Flynn Boyle (back when she had a face) is a standout, mostly because she's playing the kind of grade-grubbing perfectionist that's usually the uppity villain of most teen movies. Instead, the film understands the kind of pressure that kind of young person is under and doesn't pass judgment. Though it might be the least successful of Holland's teenage trilogy, How I Got Into College is smart and very sweet.
Dick (1999) Man, '99 was an embarrassment of riches of teen movies, no doubt kicked off by the second-wave renaissance (thanks to stuff like Can't Hardly Wait and She's All That). One of the best of that lot was Dick, a sharp political satire masquerading as a teen comedy starring Kirsten Dunst and Michelle Williams. With an insane bench of supporting actors (Will Ferrell, Bruce McCulloch, Ryan Reynolds, Dan Hedaya, Dave Foley, Teri Garr, Harry Shearer and even Ted C. McGinley) and a really funny script by Andrew Fleming, the film plays out the Watergate Scandal through the eyes of two clueless young girls. Such an underrated movie.
5. Cruel Intentions (1999) This one's a little trickier. The umpteenth reimagining of Les Liasons Dangereuses (Dangerous Liaisons for you philistines) casts a bunch of teen stars -- many of them from TV shows at the time -- and has them play spoiled rich kids fucking each other and fucking each other over at a prestigious East Coast private school. Director Roger Kumble's adaptation is surprisingly sharp and funny, largely thanks to a scene-stealing turn by Selma Blair as one of Ryan Phillippe's conquests. The love story between Phillippe and future wife (and futurer ex-wife) Reese Witherspoon is played straight, which helps ground a lot of the film's silliness. Great music, too. This movie should be terrible and isn't at all.
6. 10 Things I Hate About You (1999) I've already gone on at embarrassing length why I think 10 Things I Hate About You is one of the best of the second-wave teen movies. I won't repeat myself here.
Get Over It! (2001) There's a terrific movie buried inside the almost totally forgotten Get Over It!, which stars a pre-SUPER INTENSE Ben Foster as a high school boy who's been recently dumped and Kirsten Dunst as the girl who helps him recover. The movie is full of musical numbers (including a GREAT opening credits sequence), as the characters are all participating in their school's production of a musical adaptation of A Midsummer Night's Dream with very funny original songs. Unfortunately, the film is cockblocked by lots of early-2000s Miramax tampering: clumsy stunt casting -- I'm looking at you, Sisqo -- and horrible gross-out set pieces (still chasing the Farrelly Brothers formula three years too late) that interrupt what is otherwise a smart and funny teen movie. The musical stuff is so good and the raunchy stuff so bad that the movie winds up feeling schizophrenic.
8. Sugar & Spice (2001) Cheerleaders rob a bank to help their pregnant captain. It's a stupid premise, but the movie doesn't pretend otherwise; the girls learn everything they know from watching Reservoir Dogs, Point Break and Heat. What makes this one work -- beyond its self-aware sense of humor and brisk running time (80 minutes!) -- are the performances of Marley Shelton and James Marsden, who are incredibly sweet and simple and totally in love. A lesser movie would make fun of them for being "dumb," but Sugar & Spice recognizes how adorable and winning they both are. This is a movie that could have easily tried to go DARK but wisely resists that urge. Otherwise it would have been Jawbreaker. NO ONE WANTS THAT.
9. Not Another Teen Movie (2001) Nowadays, Not Another Teen Movie gets lumped in with Friedberg/Seltzer garbage like Epic Movie and Date Movie and Celebrity Impersonator Gets Kicked in the Balls Movie. It's much, much better than that, though, demonstrating a ZAZ-like interest in going for any and every joke possible. Chris Evans is terrific in an early performance (he should do more comedy) and Jaime Pressly plays the kind of part she was born to play/only part she CAN play. The movie has its problems -- the way it mixes first and second-wave teen movies ('80s and '90s) doesn't totally work because the references are all over the place, and there's way too much reliance on stupid poo jokes and that sort of thing -- but the movie has somehow managed to age very well. It's better and funnier than I remember it being in 2001.
Nick & Norah's Infinite Playlist (2008) Some day very soon, I'm going to write a much longer piece about this movie, which was totally and unfairly dismissed when it came out in 2008 because a) teen movies are no longer a thing, really and b) everyone decided they were tired of the Michael Cera schtick. Ok, sure. Not every single thing in Nick & Norah works; like several other movies on this list, there's an odd reliance on gross out set pieces and there are too many extraneous plot threads, but what works really works. I've said this before and I'm sure I'll repeat myself in the longer piece, but Nick & Norah is so of its time that it feels ahead of it. The movie (and the book on which it is based) understands and respects young people in a way that very few modern movies do. And because so much of the movie is about characters who love and connect over music, the soundtrack is fantastic. Even if you don't see the movie, you should buy that album.
*Almost every one of these trailers (linked to in the titles) grossly missrepresents the movies they are advertising. It's actually kind of funny, unless you're actually watching them to get a sense of whether or not I'm right about them being pretty good. Then you'll think I'm the worst.