‘Annie Hall’ At 40 & The Romantic Break-Ups It Inspired

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Anti Romantics
These are the films that (thankfully) don't see our couples find a happy ending thanks to Woody Allen's classic romantic comedy.

Photos: Everett Collection, Photo Illustration: Dillen Phelps

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The Movie: La La Land
The Couple: Sebastian (Ryan Gosling) and Mia (Emma Stone)
Their Fate: At its core, La La Land proves to be less about love and more about dreams, and while Mia and Sebastian's love story is initially charming and enviable, it deteriorates when they both become so wrapped up in their own careers they realize that they can't be there for one another. After a long separation and reconciling, they acknowledge that they're always going to love each other, even if they don't know what the future holds. In the end, they both get the careers they always wanted, and Mia marries and has a baby with someone else. They share a wordless acknowledgment of the love they once had when Mia happens to visit Seb's jazz club, and that's the end of that.
[Where to Stream La La Land]

Photo: Everett Collection

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The Movie: (500) Days of Summer
The Couple: Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel)
Their Fate: From the beginning, this film tells us that it's "not a love story". Like Annie Hall, it's often presented in a nonlinear format, and it's largely a tale of the way Tom projects his fantasies of a perfect love onto Summer and resents her when she ends things. Summer eventually marries someone else, a man she feels sure about - she was never really sure about Tom. While Tom is initially devastated, he learns to pick himself up, interviews for a new job, and asks out a new woman named Autumn. (It's okay, you can groan).
[Where to Stream (500) Days of Summer]

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The Movie: Like Crazy
The Couple: Jacob (Anton Yelchin) and Anna (Felicity Jones)
Their Fate: Things are mildly doomed from the start when Anna, an English exchange student, and Jacob, an American native, fall in love, and accidentally throw Anna's visa into jeopardy when she decides to stay with him the summer after graduation. While they attempt a long-distance relationship and evidently get married to try to get Anna's visa ban lifted. After she is finally allowed back, they uncomfortably reunite, knowing that things will never be the same due to the indiscretions during the gaps in their relationship. They stand in the shower and reflect on what they once had. (It hurts).
[Where to Stream Like Crazy]

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The Movie: Ruby Sparks
The Couple: Calvin (Paul Dano) and Ruby (Zoe Kazan)
Their Fate: This film is built on a fantasy, but the love story that exists at the helm is as real as any other. While Ruby is a character that manifests into reality after Calvin writes her, he does, for the first time since his last terrible breakup, experience romance and joy. Problematically, however, like Tom from (500) Days of Summer, he projects an idealized version of a "dream girl" onto her, and becomes consumed by controlling her. After a long, sad confrontation, he learns to let her go. It's a stunning moment of growth for the protagonist, and she does indeed disappear, though he later encounters her real-life doppelgänger in a park and perhaps embarks on this relationship with his newfound ability to love people the way that they are.
[Where to Stream Ruby Sparks]

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The Movie: Blue Valentine
The Couple: Dean (Ryan Gosling) and Cindy (Michelle Williams)
Their Fate: This film exists on the darker end of these romances, as it chronicles the demise of Dean and Cindy's relationship. Told in nonlinear format, we are shown the couple's meeting, courtship, and eventual marriage, and the couple gradually becomes hateful towards each other. Dean drinks too much and has a temper, and Cindy is withdrawn and sad. Though they try to keep things together for their young daughter Frankie and it seems like a reconciliation might be on the horizon, it's clear things are over and they just aren't good for each other anymore. Dean walks away.
[Where to Stream Blue Valentine]

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The Movie: Celeste & Jesse Forever
The Couple: Jesse (Andy Samberg) and Celeste (Rashida Jones)
Their Fate: Celeste and Jesse were best friends turned high school sweethearts who got married and are now getting divorced. They continue to pursue friendship because they think they can make this strange situation work despite the fact that they are both seeing other people. They both respectively struggle to move on, suffer a friend breakup, and eventually, the two sign their divorce papers, share one last kiss, and move on with other people. Sometimes, people really are better off as friends.
[Where to Stream Celeste & Jesse Forever]

Photo: Everett Collection

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The Movie: The Break-Up
The Couple: Gary (Vince Vaughn) and Brooke (Jennifer Aniston)
Their Fate: Brooke and Gary's break-up is the entire premise for the film, so it's no surprise when things come to a halt, but they evidently fall back in love with each other and try to win each other over in a series of ways. They eventually split up again, never having been able to make it work, and run into each other by chance on the street one day. After a brief, awkward catch up, they go their separate ways, but share a friendly, knowing smile as they part.
[Where to Stream The Break-Up]

Photo: Everett Collection

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The Movie: An Education
The Couple: Jenny (Carey Mulligan) and David (Peter Sarsgaard)
Their Fate: While this is definitely more of a coming-of-age story than a romance (and is based on a memoir), the hopes and dreams young Jenny carries about ending up with the older, charming David are crushed when she discovers he's married and has a child. She evidently goes off to Oxford to pursue her studies and independence, and explore relationships with boys her own age. (Thank god).
[Where to Stream An Education]

Photo: Everett Collection

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The Movie: The Devil Wears Prada
The Couple: Andy (Anne Hathaway) and Nate (Adrian Grenier)
Their Fate: This flick is definitely Andy's show above all, and because of her dedication to her career, her relationship with live-in chef boyfriend Nate begins to fall apart. He's ultimately fairly selfish for the duration of the film, pouting when she misses his birthday for an important work event and berating her for finding a sense of style. In the end, when they seemingly reconcile, they agree to start dating again - but let's be honest, it ain't gonna last.
[Where to Stream The Devil Wears Prada]

Photo: Everett Collection