25 of The Most Angsty Movies You Definitely Owned as a Teen

As some of us settle in to that late 20s/early 30s bracket, we might start clearing our shelves of the flicks we haven't watched in the last two years. It's like the "hanger test" for your movie collection. While sifting through some Hollywood classics, a few Best Picture nominees, and oodles of comedies that are guaranteed to make you laugh no matter how many times you've watched them, you'll probably come across a few titles that bring you careening back to your most awkward, angsty years.

Ah yes, if you were anything like me in high school, you wore black band t-shirts, listened to sad, sad emo music and had a lot of feelings. And those feelings needed to be validated by your so-hip-it-hurts collection of records, ticket stubs, and of course, movies. How else would you prove to your MySpace friends how deep you really were if you didn't have the perfect list of music, books, and movies to prove the depth of your emotions?

Take a journey back into your teen Dark Ages, won't you? Some of these movies are keepers, and some of these just have to go. Happy cleaning!

Image: Twentieth Century Fox

by Rachel Semigran

'Donnie Darko'

All around me are familiar faces, worn out places worn out faces…

Click here to buy.

Image: Adam Fields Productions

'Fight Club'

No…they were the SAME GUY!? OMG OMG.

Bonus: Brad Pitt’s abs at their finest.

Stream Fight Club here.

Image: Twentieth Century Fox

'Eternal Sunshine of the Spotless Mind'

Post-screening discussions included, “Would you erase an ex from your memory?” and “When are we going to Montauk?”

Stream Eternal Sunshine Of The Spotless Mind here.

Image: Focus Features

'The Boondock Saints'

One of the worst movies you ever owned. And yet, everyone you were friends with thought it was sooooooo cool. The guys you dated probably had the movie poster in their room, too.

Image: Franchise Pictures

'Garden State'

That monologue about pain being REAL was probably your AIM away message for ages.

Stream Garden State here.

Image: Camelot Pictures


Hey, even sad kids needed date movies. Or rather, makeout movies.

Stream Amelie here.

Image:Claudie Ossard Productions

'Requiem for a Dream'

Cripes, even the TITLE is too emo to handle.

Stream Requiem For A Dream here.

Image: Artisan Pictures

'American Beauty'

All the proof you ever needed that the suburbs were as bad as you thought.

Stream American Beauty here.

Image: Dream Works

'V for Vendetta'

Remember, remember… when Natalie Portman shaved her head!

Stream V for Vandetta here.

Image: Warner Bros.

'The Truman Show'

Because you needed back-up evidence for telling your friends that Jim Carey is actually a really great actor. It’s also a really beautiful film that still makes you cry.

Stream The Truman Show here.

Image: Paramount Pictures


You felt cool for owning it, but still never really “got” it.

Stream Memento here.

Image: Summit Entertainment

'SLC Punk'

Were you a POSER? Let this film and Matthew Lillard (!!!) help you find out!

Stream SLC Punk here

Image: Beyond Films


This was like, really deep, and like f*cked-up, you know?

Image: Miramax Films

'Empire Records'

We mustn’t dwell… no, not today. We CAN’T. Not on Rex Manning day!

Stream Empire Records here.

Image: New Regency Pictures

'High Fidelity'

This was the listicle when it was underground.

Stream High Fidelity here.

Image: Touchstone Pictures

'Dazed and Confused'

You learned about this movie from your cooler, older neighbor and it became an instant favorite.

Stream Dazed and Confused here.

Image: Gramercy Pictures

'Detroit Rock City'

Screw this small town! Screw the rules! Screw my parents! I WANNA ROCK.

Stream Detroit Rock City here.

Image: New Line Cinema

'Before Sunrise'

You discovered this film and decided it was your special secret and watched it alone and cried. A lot.

Stream Before Sunrise here.

Image: Sunrise Production


Brad Pitt AND Guy Ritchie together on one project. DUUUUH.

Stream Snatch here.

Image: Columbia Pictures


You probably owned every Kevin Smith movie just in case someone had to ask you about owning Kevin Smith movies.

Stream Clerks here .

Image:Miramax Films

'10 things I Hate About You'

Your bleeding heart was allowed one teen rom-com, so naturally you allowed yourself the one that’s based on Shakespeare. Plus Heath Ledger.

Stream 10 Things I Hate About You here.

Image: Touchstone Pictures


Even the most angst-ridden of teenage women loved and understood the world of Cher Horowitz in her platform and pleated glory.

Stream Clueless here.

Image: Paramount Pictures

'Can't Hardly Wait'

Preston Meyers talks about going to a seminar with Kurt Vonnegut… of course you loved this movie, Aman-DUUUUH.

Stream Can't Hardly Wait here.

Image:Columbia Pictures

'Kill Bill'

Pulp Fiction was a little before your time, and even when you first watched it, you couldn’t full appreciate it. Kill Bill was just funny and artsy enough to be stomached.

Stream Kill Bill here.

Image: Miramax Films

'Sin City'

Your current, more feminist-minded self hates your former self for once owning this.

Stream Sin City here.

Image: Dimension Films