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20. Animal House (1978)
Watch Animal House now on Amazon Prime Video
19. Pretty in Pink (1986)
While he didn't direct Pretty in Pink, there's little touches of John Hughes all over this socially-aware teen flick. Well, he did write it. One of his more successful movies - it made $40 million back on its teenie $9 million budget - the basic premise follows high schooler Andie Walsh (Molly Ringwald) as she dreams of dating the rich and hunky Blane (Andrew McCarthy). The path of true love never did run smooth, of course, and she finds herself debating her lot in life and whether her social status will prevent her from landing the posh totty. Luckily there's her best friend Duckie (Jon Cryer) who ensures there are always laughs just around the corner.
Watch Pretty in Pink now on Amazon Prime Video
18. 10 Things I Hate About You (1999)
What's most refreshing about this retelling of Shakespeare's The Taming of the Shrew is how the supposed 'shrew' is actually a badass feminist. That'll be Julia Styles's Kat. When she's not shredding on her guitar, she's reading The Bell Jar as a way to give the finger to the “oppressive patriarchal values that dictate our education.” At the same time, Heath Ledger is the self-appointed Aussie bad boy paid to, er, 'tame' her. There's oodles of little plot entanglements (this is Shakespeare after all) that really rev up all the teenage hormones of Kat's fellow high schoolers. The soundtrack's a late '90s gem (I Want You To Want Me by Letters To Cleo still rocks) and adult actors Larry Miller and Allison Janney get just as many laughs as the teens.
Watch 10 Things I Hate About You now on Amazon Prime Video
17. Donnie Darko (2001)
Nostalgia for '80s sci-fi kicked off in the early 2000s with Richard Kelly's filmmaking debut. At the tender age of 26 he wrote and directed this twisted, head-scratcher of a time travel movie that just so happens to be a brilliantly observed piece of teen cinema. Donnie (Jake Gyllenhaal) is not your average kid. He has visions of a giant rabbit named Frank who tells him the world will end in 28 days. During that period, Donnie goes through the same gamut of angsty teen experiences as most and then some. Alright, he basically has a month-long existential crisis. What stands out is how Kelly balances the seriousness of things (Donnie's tumultuous relationship with his mom, Donnie outing a pedophile) with some proper LOL-inducing humor. The Sparkle Motion line alone is just perfect.
Watch Donnie Darko now on Amazon Prime Video
16. Brick (2005)
A decade before he was given like, the coolest gig ever directing Star Wars 8, Rian Johnson knocked out this nifty noir. Young high schooler Brendan Frye (Joseph Gordon-Levitt) turns into a detective when his ex-girlfriend (Emilie de Ravin) turns up murdered. This ain't no comedy, folks. Brick takes its noir influences super-seriously, and our protagonist really goes through the wars trying to uncover what the hell is going on. It's like something cooked up by Raymond Chandler. This is a teen flick with 'cult classic' written all over it. JGL is fantastic in an early dramatic role, and it cemented director Johnson as a talent to keep an eye on.
