Originally published at Cinema Sugar.

1. Brick

If you found high school to be a dark, inscrutable enigma with a rigidly enforced social-class structure and impenetrable lingo, you’ll deeply appreciate Rian Johnson’s lean and masterful debut feature that renders adolescence as gritty film noir. A young, sphinx-like Joseph Gordon-Levitt investigates his ex-girlfriend’s mysterious disappearance like a teen Dashiell Hammett detective, navigating double-crosses and life-or-death stakes that feel right at home in the high drama of high school.

2. October Sky

Chris Cooper and Laura Dern would be enough for a solid cast, but even at 17 years old Gyllenhaal brings the charisma and authenticity emblematic of his now long and impressive career. (Still, the secret star: composer Mark Isham’s devastating heart-punch of a theme.) The movie is about family and friendship and science and America, but ultimately it’s about a teenager with a dream. “This one’s gonna go for miles…”

3. 10 Things I Hate About You

Heath Ledger beaming with rascally charm (and pulling off an epic lip-dub years before they were cool). Julia Styles taking no prisoners. Joseph Gordon-Levitt aw-shucks-ing his way into our hearts. Sorry Clueless: this is the best ’90s Shakespeare film adaptation and it’s not close.

4. Dazed and Confused

Tag your high-school self: were you kinda skeevy like Wooderson, mama-bear protective like Jodi, effortlessly cool like Pink, pseudo-intellectual like Tony, a live-wire bully like Darla or O’Bannion, victimized like Mitch? Dazed lives on because it’s all of us, and that’s alright, alright, alright.

5. Booksmart

This directorial debut from Olivia Wilde was charming as hell. In conjunction with the natural chemistry between Beanie Feldstein and Kaitlyn Dever as straight-laced overachievers out for one crazy night before high school ends, Wilde’s script brings the film to depths of character, understanding, and humor that are rare in debut features and especially in movies about teens.