20 Quirky Movies Every ~Hipster~ Teen Was Obsessed With

Growing up, there were certain teen movies that stayed with you as you entered adulthood. Almost always, they were indie movies featuring some kind of brooding lead character who had a whole lot of emotions, just like you. These were the movies that had some kind of classic, coming-of-age tale, that you most likely posted about all over your Tumblr. It could have been an age-old classic like The Breakfast Club or a more recent teen drama like Paper Towns.

No matter how cheesy or unrealistic those movies may seem now, they’ll always have a spot in your heart. So, here are 18 quirky movies that will stir up a whole lot of nostalgia for every former ~hipster~ teen.

1. Nick & Norah’s Infinite Playlist

First of all, let’s start off by saying that this teen movie gave a lot of young straight girls some seriously unrealistic expectations about high school romance. That may be why we loved it so much. For two hours, we watched as Michael Cera and Kat Dennings played out every ~deep~ teenage girl’s romantic dream. Nick (played by Cera) was sensitive, shy, artistic and unbelievably complicated — AKA every angsty teenage girl’s dream. *Sigh.*

2. The Breakfast Club

This movie is an absolute classic, and it’s easy to see why. No matter how many years go by, every emotion-filled, brooding teenager can relate to at least one of the characters in this coming-of-age teen movie. Released in 1985, The Breakfast Club is just as relevant now as when it first came out. It showed how deeply troubled even the toughest, smartest, weirdest, or most popular people in high school could be. It made us feel a little less alone. Plus, I think a lot of us were totally crushing on “The Criminal.” Just me?

3. Juno

Another one starring Cera, this movie was a little dicey in terms of the mixed messages it sent to young audiences, but it was still a staple teen movie for the ~hipster youth~. Pretty much anything involving Michael Cera can be categorized this way, TBH. The love between Bleeker and Juno was unusual, and the two really only understood each other. It was super romantic. Granted, this movie kind of sent the message that you can have a baby at 16, give it up for adoption and the rest of your life will be easy-peasy. All that aside, it was still a smart indie dramedy that resonated with a lot of teenagers.

4. Little Miss Sunshine

If you didn’t feel personally attacked by this movie at least one time in your life, then you were not a truly angsty teenager (spoilers ahead, BTW). The family in Little Miss Sunshine was incredibly dysfunctional, and it made us remember that we weren’t the only ones dealing with a lot of deep, complicated issues. This movie was so beautiful because it was also so devastating. Watching Dwayne (played by Paul Dano) learn that he can’t be a pilot, after dedicating his whole life to it was like a kick in the chest. Plus, Dwayne was basically a caricature of every sullen, emo dude we all had a crush on at one point — with way more depth.

5. Moonrise Kingdom

This movie isn’t exactly a teen movie, TBH, but something about watching Moonrise Kingdom as a teenager was a formative experience. Seeing Sam and Suzy run away together to pursue their young, innocent love made us feel all kinds of things. Maybe it’s because they were so young, it reminded us that true love may still exist, despite the fact that your prom date was ignoring your texts. Plus, like most Wes Anderson movies, it’s really aesthetically pleasing, which made it a staple movie on every teen’s Tumblr account for a while.

6. 500 Days of Summer

Of course, the quirky rom-com to end all quirky rom-coms, we had to mention 500 Days of Summer. This movie is, to this day, one of the most iconic ~hipster~ movies of all time. Every single girl who watched this most likely fell head-over-heels for Joseph Gordon-Levitt, who played Tom. We also wanted to beZooey Deschanel (who played summer) more than anything. The only issue with this movie is that its purpose was to portray an unhealthy relationship that was doomed to fail, which definitely flew right over the heads of its teen audience.

7. Almost Famous

Another teen movie classic, Almost Famous may be one of the most-watched movies by millennials everywhere. It pretty much summed up our entire idea of what it meant to be cool. This cult classic follows William Miller, a teen reporter for Rolling Stone who travels the country writing about all of his favorite bands and musical idols. Almost Famous showed us the less-glamorous side of rock and roll, and took our highly-charged, teen emotions for a rollercoaster ride. Plus, who among us couldn’t relate to being totally obsessed with a group of musicians?

8. Dazed and Confused

Dazed and Confused is another one of those coming-of-age cult films that just never gets old. This movie had all the makings of a ~hipster~ teen movie, and many of us hoped that one day we would be as badass as the kids in this flick.

Basically, it was just a whole lot of underage drinking, smoking weed, making out and listening to rock music. It managed to portray all the insecurities teenagers feel, even the “bad kids” who seem too cool to be self-conscious. Plus, if you remember — this is the movie where Matthew McConaughey said his now-iconic line, “alright alright alright.”

9. SLC Punk!

This teen movie was a little bit lesser-known, but had a pretty serious cult following. SLC Punk wasn’t entirely relatable for a lot of teenagers, but it was so badass, emotional and dramatic that it became a hit with high school audiences. Basically, it follows a group of hardcore punk kids in the 1980s, and the difficulties they face with violence, drugs and their moral values. Not to give too much away, but the movie shows how even the toughest people are often putting on a front and feeling seriously insecure. The ending of this movie is so heartbreakingly-realistic, it’s no wonder so many angsty teenagers became obsessed.

10. Stuck in Love

Stuck In Love is a fairly recent indie teen movie about love (both young and mature) and familial difficulties. This movie most likely became a success among teenage girls because it starred Nat Wolff, former frontman of the Naked Brothers Band (yeah, remember them?) and Logan Lerman. The movie shows how the unhealthy relationship between the parents, Bill and Erica, has affected their kids, Rusty and Kate. While Kate prefers the partying lifestyle and a more promiscuous love-life, Rusty is too shy and insecure to ask out the girl of his dreams.

11. Paper Towns

Nothing says misunderstood, angsty, hipster-teen better than anything by John Green. The famous novelist had one of his more popular books, Paper Towns turned into a film, much to the delight of his army of teen fans. This flick was another one about highly-unrealistic romance between two incredibly unusual and ~deep~ teenagers. We all wanted to be as mysterious and misunderstood as Margo, in the hopes that someone like Q would come searching for us in the name of love. Unfortunately for us, most high school boys were not Q, and we were not nearly as deep as we thought.

12. It’s Kind of a Funny Story

Like almost any book-turned-teen movie, the book for It’s Kind of a Funny Story was significantly better, but the movie was still great. The story is pretty heavy, as it deals with Craig, a 16 year-old who checks himself into a psychiatric hospital after nearly jumping to his own death. During his time there, he meets Noelle (played by Emma Roberts) and the two, you guessed it — fall in love. The characters in this movie are extremely complex and interesting, and were able to convey a lot of the feelings that tons of insecure teens are experiencing.

13. The Royal Tenenbaums

You know if we were going to mention Wes Anderson we had to mention The Royal Tenenbaums. If you want to talk about messed-up families, this is the movie for you. ~Hipster~ teens flocked to this movie like moths to a flame. It was fairly depressing, as the movie is mostly about three well-off teenagers (The Tenenbaums) who experience their golden years in their youth. The movie picks up once they are forcefully reunited by their formerly-absent father, as they’re all trying to cope with their failed adult lives.

14. Garden State

Not only was Garden State basically a bible for brooding teenagers everywhere, the soundtrack was absolutely golden. The best part about this movie is that it’s hard to say exactly what it’s about. It’s pretty upsetting, and talks a lot about being a totally apathetic adult, and follows Andrew (played by Zach Braff as he returns home to his parents at 26-years-old. A series of super-depressing events unfold as he begins a unlikely friendship with Sam (played by Natalie Portman). Plus, the whole thing is set to a soundtrack with a whole bunch of songs by The Shins, so it was bound to be a hit for the misunderstood teenager.

15. Spring Breakers

The Spring Breakers movie was definitely bizarre, to say the least. Its surprising amount of popularity probably had to do with its star-studded cast (Hey, James Franco, Ashley Benson, Selena Gomez, Vanessa Hudgens and Rachel Korine) and its eerie, neon aesthetic. This movie got pretty horrible reviews from critics, because the entire thing is a kind-of pointless, unbelievable story with a lot of bad acting. However, the fact that it had a whole lot of crime, pretty girls in bikinis, drinking and drugs made it really appealing teen movie for edgy kids everywhere. Plus, anybody who was anybody could spend hours debating that it was actually supposed to be that bad which made it good, because it’s a critique on spring break culture or whatever.

16. Sixteen Candles

Similarly to The Breakfast Club, Sixteen Candles is another timeless classic by John Hughes. This teen movie is about feeling ignored, having a crush on the popular guy, and being seriously annoyed by your family. Spoiler alert: the main reason a lot of us loved watching this movie was because it featured an unassuming, nice girl who ends up with the boy of her dreams. It gave us all the slightest hope that we too would find love like Molly Ringwald. Spoiler alert #2: most of us did not.

17. Eternal Sunshine of the Spotless Mind

Eternal Sunshine of the Spotless Mind definitely isn’t just a teen movie, but it resonated with a lot of teenagers because of how freaking deep it is. Not gonna lie, this movie may take a few watches in order to fully understand a lot of the nuance in it (at least it did for me), but it’s super worth it. Seeing the way Joel and Clementine rebuild their lost relationship is really heartbreaking and incredibly beautiful. Plus, it spurred discussion on whether you would erase that awful ex from your memories if you could.

18. Donnie Darko

A few years ago, if you asked any hip teen what their favorite movie was, there was a 99% chance they would say Donnie Darko. This cult-classic teen movie is pretty difficult to explain due to how surreal and symbolic it is, but it was primarily so attractive to teens because of how dark and misunderstood the main character is. Donnie Darko, played by Jake Gyllenhaal, begins having visions of Frank, a figure in a rabbit costume. Basically, everyone thinks he’s crazy, because Frank has told him that the world will end in 28 days. Honestly, you truly have to watch it to understand..

19. The Perks of Being a Wallflower

The Perks of Being a Wallflower is arguably one of the most well-known books for teens in our generation. Despite the fact that it often gets mocked for being a book that ~hipster teens~ read, it’s honestly a fantastic book (I swear!). The adaptation of the book is (obviously) not as great, but it was still hugely popular, starring Emma Watson and Logan Lerman. It follows the story of Charlie and his struggle with clinical depression, trauma, familial strain, and his unlikely friendship. Plus, that whole scene when they drive through the tunnel was probably reenacted by every teen who saw the movie.

20. Charlie Bartlett

Last but not least, we have Charlie Bartlett. This movie was so awesome because the main character, Charlie was a total badass. After being booted from private school after private school, he enrolls in public school. The story goes that Charlie ends up abusing the number of psychiatrists he sees, getting tons of prescription meds, and becomes a psychiatrist to the students via the boys’ bathroom. As you can imagine, this goes horribly wrong, but the whole movie is about the various issues and insecurities associated with high school, making it a go-to for every ~hipster~ teen.

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