It was a weird time. A time (the only time) when Freddie Prinze Jr. and Shane West ruled, when Mandy Moore, Julia Stiles and Kirsten Dunst were equals. When awkward musical numbers, mini-backpacks and makeover montages ran rampant. When Anne Hathaway, James Franco and (by god) Heath Ledger deigned to walk the hallowed halls of high school comedy.
  1. Can't Hardly Wait (1998)
    I have a lot of affection for this one, even though it could've been much better. Best pals Ethan Embry and Lauren Ambrose are both charming as they take separate paths to romance on graduation night. Unfortunately, Jennifer Love Hewitt is a boring dream girl who never gets to be interesting and has terrible hair. Seth Green, on the other hand, is completely weird and lovable as Lauren Ambrose's unexpected love interest. Other highlights include Charlie Korsmo's rendition of Paradise City.
  2. 10 Things I Hate About You (1999)
    A classic to this day if only because it features Heath Ledger in all his shaggy-haired Australian-accented glory, looking rather embarrassed as he belts out Can't Take My Eyes Off You. A benchmark in the classic literature (Shakespeare's Taming of the Shrew) to teen movie adaptation, it peppered such phrases as "mewling rampallian wretch" and "I burn, I pine, I perish" into the dialogue. Bonus appearances by Joseph Gordon Levitt, David Krumholtz, and the always wonderful Allison Janney.
  3. Never Been Kissed (1999)
    Drew Barrymore can get away with just about anything, even this nonsense: she's an undercover reporter who goes back to high school and falls in love with her teacher, played by Alias dreamboat Michael Vartan (it creeped me out that he was more into her when he thought she was in high school). Bonuses: David Arquette, as her popular brother who follows her back to high school, Molly Shannon and John C. Reilly as coworkers who fall in love, and a pretty great roller coaster of a 90s makeover.
  4. She's All That (1999)
    Oh god no, we can't make over Rachel Leigh Cook! She's ARTSY! The classic Pygmalion story, except extra stupid. Some highlights: Paul Walker (may he RIP) as a ridiculous jerk, Matthew Lillard as his usual obnoxious self, Anna Paquin as seriously out of place with a seriously weird attempt at an American accent. Special appearance by that Sixpence None the Richer song.
  5. Drive Me Crazy (1999)
    Against my better judgement I really love this one. Sure it's named after a Britney Spears song and stars endlessly chipper yet prematurely middle aged Melissa Joan Hart, but that's all balanced out by charming bad boy next door Adrian Grenier, and a script by Rob Thomas (creator of Veronica Mars and other great things). Here, she's the popular one who turns her outcast next door neighbor into the perfect prom date, complete with totally unnecessary makeover (now with khakis and a swatch!).
  6. American Pie (1999)
    I suppose this was an important entry in the evolution of the gross out teen comedy, but I never liked it much. What did it really give the world but some dirty flute jokes, Stifler, Tara Reid and a franchise that just kept going, trying to build on nostalgia and charm where there was none.
  7. Cruel Intentions (1999)
    This one isn't really a comedy but the hilarious, over-the-top turns by Sarah Michelle Gellar and Ryan Phillipe almost make it count. Also, it jumps right on that adaptation train that Clueless started back in '95, turning the 18th century French aristocrats from Les Liaisons Dangereuses into bratty, smug upper east side teenagers. Selma Blair, Reese Witherspoon and Josh Jackson round out the cast, and the soundtrack is 90s perfection.
  8. Down to You (2000)
    I don't remember this one at all and that's because it's totally forgettable. I'd rewatch it for this list but I probably still wouldn't have anything to say about it. Still, it does star teen movie royalty from this brief shining time in history (not the Brat Pack but the Mini-Backpack Pack?), Freddie Prinze Jr. and Julia Stiles. Actually I think it was set in college, which makes it irrelevant as this list is for high school comedies. But I liked that Mini-Backpack Pack line so I'll leave it.
  9. Center Stage (2000)
    Definitely a classic. Main character Jody Sawyer's dancing might not be up to par, but as one recruiter says during try outs, "Just look at her." She's a boring pretty blonde ballerina, sought after by a bad boy and a good boy (both of whom happen to be laughably bad actors, since they're actually very good ballet dancers). Supporting actors include Zoe Saldana and Susan May Pratt. Bonus: an epically long and totally unrealistic final performance (how does her hair and makeup change mid-dance?!)
  10. Whatever it Takes (2000)
    Supposedly a modern day high school set Cyrano De Bergerac, this one's pretty forgettable. Post Freaks and Greeks James Franco plays a weirdo popular kid to Shane West's super boring nice guy (his much more interesting sidekicks played by a nerdy Colin Hanks and a crazy-eyed Aaron Paul). Jodi Lyn O'Keefe plays the same role she did in She's All That. Best part (other than Aaron Paul): love notes are composed on iMacs and sent via this newfangled thing called email.
  11. Bring it On (2000)
    An instant classic. The tooth brushing scene alone puts the charm in charming. By far the best of Dunst's inexplicably prolific batch of teen movies. (She could've been doing great things but I kind of love that she was doing this.) Also glad the adorable Jesse Bradford got his moment as a leading man, chuck taylors, clash t-shirt, crooked grin and all. Bonuses: Eliza Dushku and Gabrielle Union as badass cheerleaders.
  12. The Princess Diaries (2001)
    A classic ugly duckling story in which frizzy haired, bespectacled Anne Hathaway becomes shiny and contact lensed. She's clumsy, she has a grumpy cat, she lives in a converted firehouse, and her best friend is Heather Matarazzo. She's also a princess and Julie Andrews is her grandmother. What's not to like about any of that? Add to that the awkward love interest played by Jason Schwartzman's little brother, who's in a band and fixes cars. Perfection.
  13. Get Over It (2001)
    Featuring a high school production of A Midsummer Nights Dream, complete with Backstreet Boy-esque musical numbers, Kirsten Dunst, who is better than almost everything she appears in, Ben Foster, who will go on to be a badass but appears here as an adorable little ginger boy, Zoe Saldana, Mila Kunis, Colin Hanks, and serious artifact of the time Shane West, totally ridiculous as a former British boy band member. Plus Ed Begley Jr., Swoosie Kurtz, Martin Short and of course Sisqo and Vitamin C.
  14. Crossroads (2002)
    All I remember about this movie is the weird casting of Britney Spears as high school valedictorian. And when she gets naked with fellow nerd Justin Long her abs look distractingly like those of a pop star. It's a road trip movie and her best buds are Zoe Saldana and Taryn Manning. It was written by Shonda Rhimes and directed by Tamra Davis. I probably liked it but I forget.
  15. A Walk to Remember (2002)
    The beginning of Mandy Moore's reign as a soulful teen heroine. She's the good, God-loving girl to Shane West's (can you believe it) bad boy. It's not really a comedy and *spoiler alert* she even dies at the end, but there's something about this one that stands out in this short but prolific teen movie era. It's actually pretty sweet, and Moore earns her spot as B movie royalty for the next 5-8 years.