Ferris Bueller’s Day Off (1986)
The first time I saw FBDO I was not quite a teenager, and this movie lit up my every wish of what high school would be like: stealing parents’ cars, pulling pranks, skipping class, getting away with everything. To be a teen was to be Ferris Bueller was to be wild and loosed upon the world. Matthew Broderick plays Ferris, a charismatic high school boy who engages in all manner of hairbrained shennaniganery in order to skip school for a day with his girlfriend, Sloane (Mia Sara), and his head-case best buddy, Cameron. Every time I watched this movie I imagined which character I would be like as a teenager. You want to be Ferris, the courageous antihero, but you also want to be Sloane—firmly ensconced in the power position of being the #1 girl of a boy who controls the world (plus, the accent and the white leather fringe jacket), though most of the time I knew I was probably headed for Cameron territory, sans the whole standing-up-to-his-dad monologue (or maybe if we are truthful, I was the warm-Gummi-bear girl). I liked the Ferris version of being alive and in/out of control; it was much more appealing than other cinematic portrayals of high school at that time—the drugs, death, and privilege of Less Than Zero or the more realistic caste-system misery of The Breakfast Club—because it was fun. Every adult in the movie is an idiot, which is the most unifying truth of being in high school, is it not? That sense that you are bursting to live and be free connects you to Ferris in every frame of this film. SAVE FERRIS. —Jessica

National Lampoon’s Vacation (1983)
The ultimate family road trip comedy finds Chevy Chase playing the bumbling paterfamilias of the Griswold clan. As they make their way across the country to Wally World, everything that could possibly go wrong does, and it’s all very, very funny and very, very Chevy Chase-y (so, super goofy). Vacation, which was written by John Hughes, was released the same year I was released from my mother’s womb. Is that just a coincidence, or was I just really anxious to see this movie? There’s no way to be certain but I do love the movie enough to watch it whenever it comes on TV (and that’s a lot), and when I get married, I’m probably going to walk down the aisle to Lindsey Buckingham’s “Holiday Road” (the Vacation theme). —Amber

The Point (1971)
Harry Nilsson was inspired to make this movie (and its accompanying soundtrack album) when he “was on acid and looked at the trees and realized that they all came to points, and the little branches came to points, and the houses came to points.” He thought, “Oh! Everything has a point, and if it doesn’t, then there’s a point to it.” This ultra ’60s/’70s vibe dominates the music, the dialogue, the happy animation, the spirit, and the point of the movie. In the film, Oblio is a little boy in the Land of Point who was born with a round head. This isn’t chill, because everyone in the Land of Point is supposed to have a point. So Oblio is banished, with his dog, Arrow, to the Pointless Forest. On the road to the forest, Oblio meets many friends whose voice actors are probably on acid, such as a rock man, giant bees, and a leaf vendor. He eventually realizes that not everything has to be pointed in order to have a point in life. Regardless of the constant puns and the “whoa man” vibes, I hope that this movie points you in the right direction. —Olivia

Almost Famous (2000)
Fifteen-year-old William Miller wants to be a rock & roll journalist; the problem is that there is nothing rock & roll about him. He’s earnest and nerdy! He doesn’t do drugs, and he respects his mom! If he weren’t a fictional character, your parents would probably love it if you dated this guy! (Actually, this movie is loosely based on the early life of Cameron Crowe, who also made very important teen movie Say Anything.) But with a little luck and perseverance (and his big sister’s hand-me-down record collection), he starts writing for underground music papers, then is miraculously assigned to go on tour across America with the fictional band Stillwater to profile them for Rolling Stone magazine, whose staff has no idea that he isn’t even old enough to drive. William is thrown into a world of alluring groupies, luxury hotels, experimental drugs, shaggy hairdos, and hairy situations (ba-dum ching!). My favorite thing about movie, besides the fact that it is just plain beautiful and funny and touching, is that William’s mom, Elaine, played by Frances McDormand, is a constant presence throughout, whether she’s dropping William off at a concert and embarrassing him by yelling, “Don’t take drugs!” or by harassing Stillwater and their entourage via hotel telephone. The band’s guitarist, Russell, thinks he’s a hardened rock star, but when Elaine lectures him over the phone about keeping her son out of danger and asks him, “Do I make myself clear?” and he answers “Yes, m’am,” you see him becoming 15 years old again before your eyes. If you’re like me, you’ve had times where you felt like your innocent ideals and honesty prevent you from being “cool.” Almost Famous serves as a good reminder that sometimes the best thing we can be is uncool. FUN FACT: Patrick Fugit, who plays William, grew three inches during filming and some of his costars had to wear platform shoes by the end of production to keep things looking consistent. —Gabby

Bill Cunningham New York (2010)
This movie is a sermon about work, and a poem to New York. Long before the Sartorialist came around, there was Bill Cunningham, the OG street-style photographer, whose work broke ground in Women’s Wear Daily and the New York Times in the ’70s and Details magazine in the ’80s (it was a real culture and fashion magazine then, and not the sweaty dudefest it is today). Now in his 80s, Cunningham still works at the Times and still rides his bike all over New York, taking hit-and-run pictures of interesting-looking people and sussing out weekly trends (way before the fashion press has taken note) for the paper. He lives on very little; he’s a monk whose religion is his work. He doesn’t accept money when he doesn’t have to, he sleeps on a pallet on the floor, and he devotes his life to making good things. This movie taught me everything I have ever needed to know about creating things, about working, and about LIFE IN GENERAL. If you want to make a life around any kind of creative practice, if you are trying to figure out how not to sell out, if you are interested in fashion and/or photography, if you live in or love New York, if you like documentaries in general, if you have a soul—you have to see this movie. (It’s on Netflix.) —Anaheed

North by Northwest (1959)
Shot in incredibly vibrant Technicolor, North by Northwest tells the story of a man (played by the handsome and charming Cary Grant) who believes he has been mistaken for someone else and that he is being watched. There are chases involved, featuring a wide array of American landscapes, including an iconic scene at Mount Rushmore. The scene on the train between Grant and Eva Marie Saint, though tame by any of today’s standards, is one of the steamiest scenes ever (made more so by its subtlety). This film is visual gold, and the suspense will keep you at the edge of your seat! It will also make you want to travel the country and be in the middle of a giant mystery. —Tara

Natural Born Killers (1994)
People are often shocked to learn that this is one of my favorite movies, because I’m this pacifist vegan girl, and Natural Born Killers is one of the most violent and twisted road trip movies of all time. It’s about Mickey and Mallory, lovers played by Woody Harrelson and Juliette Lewis, who go on a mass murdering spree across the Southwest that is glamorized—in fact, encouraged—by the mass media. The 24/7 news culture and our obsession with/glorification of crime fascinate me, and especially back in 1994, this movie felt like a really bold statement about all that. Also, while Mickey and Mallory do some truly reprehensible things, there moments when I can’t help rooting for them—like when Mallory beats the crap out of and kills some dudes who sexually harass her, and there are flashbacks to her traumatic childhood. It’s also visually stunning—M&M are on a murder spree across one of the most beautiful parts of the country, after all—and the soundtrack, produced by Trent Reznor, is one of my favorites of all time. —Stephanie

Crossroads (2002)
Before Britney had her babies, before Britney shaved her head, before Britney’s bank accounts had to be taken over by her father, there was a small sliver of time when it seemed like she might make it out of adolescence OK. We know now that she had a rocky entrance to adulthood, at best. But back in 2002, when she starred in this road movie with Zoe Saldana, Taryn Manning, and a guy with a face like a moose named Anson Mount, there was still hope. I saw it when it came out in the theater—I too was not a girl, not yet a woman then—and I loved it. It’s not a great film, but it is a perfect snapshot from a moment in time when things could have gone either way. —Emma

Paris, Texas (1984)
This movie is a thing of beauty; a visceral, poetic experience. Set to bluesy slide guitar by Ry Cooder and featuring cinematography reminiscent of William Eggleston’s photos, it follows a man named Travis, who’s wandering through the desert, seemingly in shock from some kind of traumatic experience. As we travel with Travis, we learn about his family, his past, and what the heck happened to him to get him where he is. There are beautiful scenes in rest stops, diners, and gas stations in the middle of the American nowhere, and discoveries of hidden weirdness in pockets of the South and the West. Harry Dean Stanton plays Travis, and he is just incredible; and so is everyone else in the movie, including Hunter Carson, who plays Travis’s son, and Nastassja Kinski, who plays his wife. And let’s not forget the mohair sweater that Kinski wears through much of the movie, over which Leeann swooned here! —Tara

The Adventures of Priscilla, Queen of the Desert (1994)
This movie is touching and so, so funny. There’s the perfect amount of ABBA, elegantly kitschy dance routines, and men wearing shimmering, sequined costumes with massive silver capes that billow in the breeze. What more could you want from a movie? What more could you want from life? Hugo Weaving plays a drag queen who’s asked to perform at a resort in a remote Australian town. He brings his two friends, Adam/Felicia (Guy Pearce) and Ralph/Bernadette (Terence Stamp), and they travel through the Outback in a rundown bus dubbed “Priscilla.” The trio encounter intolerance and confusion at many stops along the way, but are always resilient and uncompromising about who they are. The movie is gorgeously shot (the way the bright, Academy Award-winning costumes contrast with the desert landscape is simply stunning) and so much fun. You’ll laugh, you’ll cry, you’ll head to your nearest sewing machine and make a dress out of flip-flops. —Amber

My Girl (1991)
My Girl follows the very special best-friendship between Anna Chlumsky (as Vada) and a post–Home Alone #1, but pre–Home Alone #2, Macaulay Culkin (as Thomas J.) as they bicker, jump into lakes cinematically (cuz, well…), and even kiss each other on the lips! Thomas J. is obvs in love with Vada, but Vada is in love with her teacher (a very dangerous dynamic, ESPECIALLY at the age of 11). She is also obsessed with death; her mother died when she was a baby, and this majorly plagues her. It doesn’t really help that she and her father (Dan Aykroyd!) live in a funeral parlor. I’m not going to spoil the end of the movie, but I’ll just say that it involves some deep bee stings, Jamie Lee Curtis in a bunch of sexy ’70s pantsuits, and the road to de-obsessing. —Olivia

Mystery Train (1989)
I’ve always been fascinated with Elvis—not as much as an actual entertainer, but more as a representative of a certain era of machismo and kitschy Americana. This is probably why I love Mystery Train so much. The movie follows three sets of people as they pass through Memphis, all ending up at the same hotel. Though Elvis himself is long since dead by the time the movie takes place, his spirit lingers—through a pair of Japanese tourists obsessed with all things Graceland, to the actual literal ghost of Elvis giving counsel to the hotel tenants after hours. —Anna

Paranoid Park (2007)
Alex, a 16-year-old skater in Portland, discovers a skate park called Paranoid Park, where he befriends two older and more rebellious locals and ends up accidentally killing a security guard while attempting to hop a freight train (that isn’t a spoiler; it’s what sets the plot going). Set to classical music and featuring Gus Van Sant’s characteristic slow-motion sequences, the movie captures Alex’s loneliness and the weight of his crime, and gets all the details about being a real teenager in America right. —Tara ♦