Groundhog Day (1993)
Saying this movie is a masterpiece is like saying Sriracha sauce is merely a good hot sauce and not the greatest hot sauce ever invented to slather on every edible thing that exists. Bill Murray plays an incorrigible narcissist whose job as a local weatherman takes him to Punxsutawney, Pennsylvania, to cover the Groundhog Day celebration, a yearly tradition he loathes. Because of a blizzard, Bill Murray—who in the most classic of ironic twists is named Phil just like the groundhog—is snowed in for the night, only to wake up and realize that he is stuck in some kind of cruel time warp that forces him to relive the same day (Groundhog Day!) over and over again. So what happens to a person who has experienced the same day thousands of times? Well, if you’re Bill Murray’s character, you punch away annoying people in the street, experiment with all the different ways to kill yourself, take up all the hobbies that you never had the time for before, and obsessively try to win over your producer, played by Andie MacDowell, even though she is so kind and pure-hearted that it’s almost obscene and would never love a tainted, miserable lout like you (you = Bill Murray; congratulations). You know how sometimes you try to do that ill-advised thing of becoming the person you think the person you like wants to be with? And you know how it never really works because you can’t really be someone else’s idea of a good person because you can only ever be who you are? Well, imagine if you have one million chances to try out every single combination of personalities and pick-up lines on this hypothetical crush, and BOOM, you’ve just imagined the premise of Groundhog Day. As funny as this movie is, it’s also kind of…profound? Because what is life anyway but a series of the same fucking thing over and over and over again? And god forbid you should be the Debbie Downer who points that out and refuses to smile at the scripted rituals that the rest of society expects to you participate in. Somewhere between misanthropy and clarity, we find our anti-hero, Bill Murray, doing what he does best, being a hilarious asshole you can’t help rooting for, and if you think I just got deep, well girl, you just thought right. —Jenny

Annie Hall (1977)
This is the kind of movie to watch when you are down on love troubles, because it will help you keep a sense of humor about the stupid complexity of it all. (Until you give in and watch Music and Lyrics and question the meaning of life through tears and Oreo bites, that is.) It is about a relationship that exists and then doesn’t, told in flashbacks and monologues and…I swear it’s less pretentious-artsy than it sounds, because it is also FUNNY and ridiculous and Woody Allen hates himself too much for it to be that serious. Diane Keaton is amazing, but I always get annoyed when Annie Hall is classified as a Manic Pixie Dream Girl, because she has her own aspirations and (SPOILER) fulfills them, regardless of the lovable-loser Woody Allen character, whatever his name is—he basically plays himself in every movie and they may as well all be called Woody Allen by Woody Allen Starring Woody Allen Playing Woody Allen. But this one, this one is called Annie Hall. And you will fall in lurve with her. —Tavi

Fatal Attraction (1987)
Fatal Attraction is the best stalker movie ever made. I think a lot of people will call me lame when I say I’ve seen it literally 20+ times, but whatever, I just love crazy people too much. Glenn Close plays Alex Forrest, a cool and sexy businesswoman who can apparently wear a white linen suit in the pouring rain and still look awesome. Michael Douglas plays Dan Gallagher, a high-powered dude who has it all (great job, cute kid, loving wife) but because he’s a dumb loserface he has a one-night stand with Alex Forrest. But it’s more than a one-night stand for Alex…WAY more. Then she goes nuts and it’s the greatest. Like, “Hey, Dan, play this cassette that I made for you while you’re in the car driving home from work. Oh btw, it’s a tape of me threatening you like crazy. Oh btw again, I’m driving in the car behind you as you listen to this tape!” Or the movie will cut to a scene of just Alex sitting by the telephone, flicking the light on and off, waiting for a call from Dan. Creepy, right? See it and weep! —Hazel

Swimfan (2002)
Swimfan is like a Fatal Attraction for teenage audiences. The story goes: boy sleeps with girl, girl seems normal, everything seems cool, but actually the girl is a nutcase who will kill in the name of an obsessive crush. Awww, now that’s love! Swimfan is sort of cheesy and a little unbelievable, but that always translates to “BEST MOVIE EVER” in my book. Some intense cello is played! Some sex is had in a swimming pool! Some aggressive IMing happens! Also who doesn’t love a twisted teen? Definitely not me, ’cause I live for that shit. —Hazel

Bye Bye Birdie (1963)
This movie is just so ridiculous and happy and secretly creepy that I just don’t care to socialize with anyone who cannot find SOME kind of good or humor in it. Ann-Margret plays KIM MCAFEE, a fangirl who is nominated to kiss Elvis-esque teen heartthrob CONRAD BIRDIE on television, but she is dating the very jealous HUGO PEABODY. I know! You already love it! It is made only more amazing by the fact that Ann-Margret DATED Elvis in real life! She is so dreamy in this, and all the ’50s clothes will make you swoon. There is also a marriage subplot with Dick Van Dyke and Janet Leigh, which I would be all yawn about since it’s about olds, but it’s the chimney sweep from Mary Poppins and the shower victim from Psycho, so it’s actually one of my favorite subplots on planet earth! God, what else? Oh yeah, it is kind of sexist and weird but like, one of those things that is too old for it to be worth being angry about, so you just have to roll with it and think about how fun it would be to be a full-blown Justin Bieber fan just to be part of the weirdly spiritual activity of screaming with a mob of other girls at a male in tight pantaloons. —Tavi

The Incredibly True Adventure of Two Girls in Love (1995)
This movie was so good I was crooning at the screen and clawing at my face with love and appreciation throughout. I’m so happy it came into my life. It’s really rare that I find a film that I connect to as a queer person, you know? But I could see myself in this. It had little moments that made me go, “That happened to me too! I get you 100%!” That is so rare. Not that heterosexual films aren’t enjoyable and their romances not enthralling (if you’re a bird, I’m a bird, Ryan Gosling) but this film really gets me. For example: the scene at the diner, which showed the dilemma of holding hands. Just HOLDING HANDS with your honey. So simple, right? But for us homos, it’s super complicated. I’ve been on the subway with my lady and felt so afraid to hold her hand for fear of other people’s reactions, so this felt 100% legit. This movie is so romantic because it has these moments where you can see the genuine joy of two people just getting to know each other and being with each other and getting to know themselves at the same time. It’s not all happy, and the lives of the main characters aren’t perfect, but overall this film was like a big hug and a reassuring pep talk from a big sister about how normal being gay is and how it is OK. WATCH IT. —Arabelle

Fear (1996)
A good girl falls in love with the bad boy, and all hell breaks loose. Fear is like a Lifetime movie but with a not-terrible ending. Nicole (Reese Witherspoon) is courted by David (Mark Walhberg), a boy from “the wrong side of the tracks”—and also obviously a man and not a boy, but I guess this is Hollywood—and even though the first time he appears you’re totally screaming “BAD NEWS BEARS” at the screen, Nicole can’t hear you and so their relationship progresses until it climaxes in possibly the best rollercoaster scene ever to be captured in a movie. Like in all good horror movies, after Nicole loses her virginity, shit gets crazy and David gets violent and jealous and gives himself a tattoo on his chest that says “NICOLE 4 EVA,” which is all the proof you need to know that dude is deranged (other signs include stealing a picture of her family and replacing the dad’s head with his own). The movie gets super intense for sure, but mostly it is full of hilariously bad decisions that can really be traced back to Nicole’s best friend, Margo (Alyssa Milano). Actually, now that I really think about it, this movie is REALLY the classic tale of “good girl led astray by her totally nutso BFF.” I mean, they go to a party and Margo immediately starts grinding on the ONE dude who’s obviously in his 30s and DEFINITELY a criminal. You will cringe, you will laugh, you will scream, you will listen to the same Bush song like three or four times, but in the end, you will love this movie. Definitely watch with friends for maximum LOLs. —Laia

Eternal Sunshine of the Spotless Mind (2004)
Early on Jim Carrey’s character says, “Why do I fall in love with every woman I see who shows me the least bit of attention?” That line is me in a nutshell and after hearing it, I was a goner—I got a big ol’ crush on this movie. The unconventional love story is about a man who undergoes a non-surgical procedure to have his ex-girlfriend (played by the always awesome Kate Winslet) erased from his memory after learning that she’s done the same with her memories of him. It’s a relationship movie, but it’s also more than that. Eternal Sunshine looks at the importance of memory and how the things that we’d rather not remember are sometimes inextricably tied to the moments that we do want to hang on to. It’s science fiction that doesn’t really feel like science fiction. It’s fun, it’s magical, and it’s also sad in very subtle, beautiful way. —Amber

When Harry Met Sally (1989)
This is one of the best “romantic comedies” to ever exist. It is about Billy Crystal and Meg Ryan trying to answer the age-old (fake) question of whether heterosexual women and men can ever be just friends, with no desire to have sex with each another. It’s a romantic comedy, so you can probably guess exactly how everything pans out, but you will find yourself caring about these characters so much that it is worth watching even though you know the plot won’t really keep you on the edge of your seat. Meg Ryan is just so sweet and funny and Billy Crystal is just so sweet and funny and by the end you feel like you’ve eaten Mickey Mouse-shaped pancakes, that is how sweet and funny it is. It is filled with gems such as the “white man’s overbite” and the fake-orgasm diner scene. As my dad likes to remind me frequently, we have eaten in that deli, along with billions of other New Yorkers and tourists HARRY AND SALLY. —Tavi

Young Adult (2011)
This movie blew me away. Diablo Cody wrote it, that’s why. The plot: YA author Mavis Gary (pushing 40, freshly divorced, hung over every AM) gets an email announcement from her high school sweetheart’s wife, proudly announcing the birth of their child. Mavis becomes obsessed and decides that she’s going to get her ex back. She is the only member of this karass to have left their tiny hometown; she drives back there listening to the same song from an old make-out cassette tape the entire way (“The Concept” by Teenage Fanclub). This movie is not pretty—I experienced some pretty sick heavy cathartic discomfort—but it was so worth it. (Your experience will be entirely different.) This is an important movie that gives some much needed insight into (my) Generation X(cellent). The details will amaze you, as will Patton Oswalt. —Sonja

Harold and Maude (1971)
SO MANY TEARS. This is about a morbid young man who drives a hearse and a delightful old lady who introduces him to hookah smoking, grand theft auto, and, most important, love. When I say SO MANY TEARS, I mean sad-happy tears. Like how I get when I think about how beautiful and strange life is, or when I successfully get those Sing-a-ma-jig things to harmonize while I am at the Jewel. Also, the soundtrack is entirely Cat Stevens! Also, it was made in the ’70s, so everything is grainy and saturated and pretty! Wahhhhh. —Tavi

Kicking and Screaming (1995)
Ostensibly about love and post-collegiate life, this movie, Noah Baumbach’s first, is really about a group of friends who are obsessed with staying young and hip and witty, and are constantly trying to outdo one another. Extra points for super-’90s fashion, and one of the best ensemble casts ever: Eric Stoltz (Some Kind of Wonderful), Josh Hamilton (The House of Yes), Olivia D’Abo (The Wonder Years), Chris Eigeman (Metropoltian), Parker Posey (Party Girl), Jason Wiles (Beverly Hills, 90210), and more. —Emma S.

Pretty in Pink (1986)
Whenever I talk about Pretty in Pink, I spend 10 seconds discussing the plot and the next six hours talking about Duckie Dale’s clothes. Like, sometimes I watch this and think, Duckie is the best! and other times I’m all, Ugh, Duckie, you are venturing into total Brian Krakow territory, and also the knowledge that you will one day star in Two and a Half Men makes me want to weep! but I always appreciate the clothes. I mean: bolo ties, checkered vests, creepers, fedoras, plaid pants??? It was like a thrift store threw up on him in the best way possible. AND THE OTIS REDDING SCENE!!! Oh god, the Otis Redding scene. But there is more to this movie than just Duckie, I swear. Molly Ringwald plays Andie Walsh, her coolest/most iconic role ever. Andie is a DIY queen with a teen bedroom to die for. And she works at a record store and her boss has the BEST fucking hair and dresses. Then there’s the kickass soundtrack! And the strangely appealing young James Spader! And the Otis Redding scene! You guys, I really love the Otis Redding scene. —Anna

Some Kind of Wonderful (1987)
Of all the teen movies written by John Hughes, this has to be the most underappreciated. Eric Stoltz plays Keith, a working-class kid who asks out super-popular Amanda Jones (Lea Thompson). When Amanda says yes, Keith’s platonic BFF Watts (Mary Stuart Masterson) starts to realize that she has feelings for him. If you love Pretty in Pink, you’ll love this one too. In fact, the two movies complement each other—not only do they deal with some of the same issues, but both have protagonists with red hair. Anyone who has (or has ever had) a crush on a close friend needs to watch this movie. Better yet, watch it with your crush! Seriously. Do it. —Amber

Say Anything (1989)
John Cusack’s character, Lloyd Dobler, became famous for being the iconic Perfect Boyfriend and for holding a boombox over his head outside Diane Court’s bedroom window. Diane is this unattainable girl, but what places her so far out of reach is that she’s “a brain” and has ambition, not that she’s beautiful (even though she is; I mean hello she is Ione Skye). And what makes Lloyd perfect isn’t that he’s super hot and successful (he isn’t either); it’s that he’s devoted to Diane and happy to play a supportive role in her big life plans. This is one of the best romantic comedies of ALL TIME and if you don’t agree you have a piece of chewed-up garbage where your heart oughtta be. Watch it with your crush, and you never know what will happen! I saw it (in the theater! I’m old) with a TOTALLY PLATONIC buddy and as we walked out he asked if I wanted to be boyfriend/girlfriend. Say Anything is a secret love potion! —Anaheed

Vertigo (1958)
This movie really creeped me out, but in a really really good way. I was also weirded out and confused and hopeful—basically, Vertigo is a rollercoaster ride. The fever of James Stewart’s emotions is palpable, and I mean, dressing your new girlfriend up as the women you used to be in love with is a little on the obsessive side. The storyline is really arresting, and the visuals are really washed out and eerie. I still haven’t forgotten the nightmarish green of the hotel sign, or Kim Novak’s profile. All in all, pretty perfect. —Naomi

(500) Days of Summer (2009)
There are at least 500 different reasons why I’m crazy about this adorable anti-romantic comedy, but because it would take 500 seconds (give or take) for you to read that list, I’ll give you the top five. As a kind of homage to the film’s nonlinear narrative, the numbers are non-sequential. (3) There’s a Hall & Oates dance interlude. (5) Joseph Gordon-Levitt sings “Here Comes Your Man” and if you close your eyes, you can pretend he’s singing to you. (2) Zooey Deschanel sings “Sugar Town” and if you close your eyes, you can pretend she’s singing to you. (4) This quote: “Just ’cause some cute girl likes the same bizzaro crap you do, that doesn’t make her your soul mate.” Those of us who crush hard and take our pop culture seriously should always remember these wise words. (1) The movie is cute and quirky but it’s also one of the most honest depictions of a relationship (the highs, the lows, the end, the beginning, the stillness, the expectations, the exasperation, the Sid and Nancy of it all) that I’ve ever seen. —Amber

Crumb (1994)
In high school, I was told by my teachers that it was OK to be an outcast because one day I would turn my weirdness into art, into something that other people would value and appreciate, but no one ever mentioned what happens to the outcasts who don’t achieve redemption. This documentary by Terry Zwigoff (who directed Ghost World), about the radical comic-book artist R. Crumb and his brothers, Charles and Maxon, takes a weird, tender, and intimate look at both of those possible outcomes, contained in this one family. The brothers grew up fearing their abusive disciplinarian of a father and being humiliated by their peers. Two of them don’t fare so well: Charles, the oldest one, who drew comics as a kid and influenced his brothers to start drawing them too, eventually becomes a middle-aged shut-in living in his mother’s basement, medicating himself against depression and anxiety until he’s nearly catatonic. (He killed himself not long after this movie came out.) The youngest one, Max, becomes a self-punishing ascetic who sleeps nightly on a bed of nails. Meanwhile, Robert becomes the legendary artist R. Crumb, lauded and reviled by critics for his brilliant, garish, often perverted, drawings. (Cue Le Tigre singing about John Cassavetes: “Misogynist? Genius?” Crumb, like Cassavetes, is probably both.) He somehow managed to turn his obsessions into art. But what about the rest of us? What about people who don’t have the ability to save ourselves from the madness of our obsessions? When Max calmly reveals to the camera that he’s a registered sex offender, it becomes clear how scary and tenuous that line is between a sick obsession as in “that’s a sick-ass Nirvana shrine right there” and “that’s a sick-ass creep right there.” And man, I really want to stay on the right side of that line. —Jenny