One of the most enduring breakup movies of all time serves as the inspiration for Ariana Grande’s latest album, Eternal Sunshine, which maps the downfall of her marriage and subsequent headline-making new relationship. That would be 2004’s Eternal Sunshine of the Spotless Mind, in which exes Joel and Clementine (Jim Carrey and Kate Winslet) undergo procedures to erase one another from their respective memories after splitting.

In the hours after Grande’s record was released, viewership of the 20-year-old movie has doubled on Vudu, according to Fandango. And the music video for one track, “we can’t be friends (wait for your love),” recreates famous shots from the film. Many other artists have used breakup movies as reference points for their work as well—from Netflix’s Someone Great inspiring Taylor Swift’s 2019 song “Death by a Thousand Cuts” to SZA’s recent Grammy-nominated track, “Kill Bill,” a nod to the 2003 film.

Given the universality of heartbreak, there’s often a cyclical nature to these things: A real-life split inspires a movie, which influences a song about another’s romantic misfortune, and so on. As we celebrate the latest breakup-movie-to-music entry, we look back at some of the best breakup movies of all time, presented in chronological order—from Casablanca’s “Here’s looking at you, kid” to the in-yun of Past Lives.

Casablanca

Release year: 1942

Director: Michael Curtiz

Notable cast: Humphrey Bogart, Ingrid Bergman

This best-picture winner is synonymous with five little words: “Here’s looking at you, kid.” It’s what Humphrey Bogart’s Rick Blaine utters to his former flame Ilsa (Ingrid Bergman), who reignites their past love affair upon her arrival in Casablanca with her husband, Victor Laszlo (Paul Henreid). Even if you haven’t seen the classic film, you know how this one goes down, thanks in large part to persistent references in popular rom-coms from When Harry Met Sally to The Holiday.

The Graduate

Release year: 1967

Director: Mike Nichols

Notable cast: Dustin Hoffman, Anne Bancroft, Katharine Ross

Dustin Hoffman’s breakout film hinges on two separations—the first from his aimless Benjamin’s unlikely friends-with-benefits relationship with Mrs. Robinson (Anne Bancroft), and the second involving that woman’s more age-appropriate daughter, Elaine (Katharine Ross). The icky optics of that aside, the movie’s most important breakup is the one we don’t actually get to see yet know is coming from the second Benjamin Braddock bursts through church doors shouting Elaine’s name on the day of her wedding to another man. An ill-planned public display of affection from a desperate man rarely makes for a shrewd romantic move.

The Way We Were

Release year: 1973

Director: Sydney Pollack

Notable cast: Robert Redford, Barbra Streisand

In a second-season episode of Sex and the City, Carrie Bradshaw explains that there are two types of women: “simple girls and Katie girls.” She’s talking about Barbra Streisand’s character in this heartbreaking classic, a passionate activist who falls for Robert Redford’s Hubbell, a jock with a secret talent for writing. Their separate outlooks on the world are eventually the couple’s undoing. Streisand, who also sings the film’s beloved title song, wrote of the movie in her recent memoir: “I, too, love The Way We Were and consider it a highlight of my career. I think it’s one of Bob’s best performances…and probably one of mine as well…and I’m thrilled whenever I see us listed as one of the screen’s most romantic couples. We made something that will last a long time…much longer than most real marriages.”

Scenes From a Marriage

Release year: 1974

Director: Ingmar Bergman

Notable cast: Liv Ullmann, Erland Josephson

Before HBO’s 2021 limited series starring Oscar Issac and Jessica Chastain, there was the then groundbreaking original film about Marianne (Liv Ullmann) and Johan (Erland Josephson), a once picture-perfect couple now picking up the pieces of their failing union. The film’s minimalist legacy can be seen within a range of projects in the years that followed, from Woody Allen’s Husbands and Wives to Sam Levinson’s Malcolm & Marie. In its immediate wake, the movie allegedly sparked an uptick in family counseling appointments in Sweden—as well as an alleged increase in divorce rates. Ingmar Bergman is on the record as saying this aftermath made him “incredibly happy” because people were inspired to leave situations that no longer served them.

The Shining

Release year: 1980

Director: Stanley Kubrick

Notable cast: Jack Nicholson, Shelley Duvall, Danny Lloyd

The Shining often gets classified as pure horror, or a Stanley Kubrick masterpiece, or even a highly referenced quote generator. But at the crux of everything is a really, really bad breakup between Jack Nicholson’s maniacal author Jack Torrance and his long-suffering wife, Wendy (Shelley Duvall). The film’s most terrifying sequences mine the depths of our sympathies for Wendy as she watches the man she loves lose his mind. Honestly, who among us hasn’t felt like they were fleeing from an ax murderer during a particularly brutal breakup?

Heartburn

Release year: 1986

Director: Mike Nichols

Notable cast: Meryl Streep, Jack Nicholson, Jeff Daniels, Stockard Channing

Nobody plays a heartbreaker quite like Nicholson, who, in Heartburn, has the audacity to screw over his pregnant wife (played by Meryl Streep) in humiliating fashion. The film is based on Nora Ephron’s 1983 novel, a thinly veiled account of her real-life split from Watergate journalist Carl Bernstein. (This photo of the former couple pretty much sums it up.) The book and its film adaptation are a scathing indictment of a husband’s flagrant infidelity—and naturally, a complicated project for the couple’s actual son, filmmaker Jacob Bernstein. “It was very hard to separate the book from the affair because I knew about the affair from the book,” he told NPR in 2021. “I definitely found it out from kids at school whose parents had either read the book and told them about it, or on a couple of occasions actually took their children, who were right around my age, [to the movie]. It was an odd set of circumstances, for sure.”

The War of the Roses

Release year: 1989

Director: Danny DeVito

Notable cast: Michael Douglas, Kathleen Turner, Danny DeVito

Who gets to keep the house? It’s a customary question in divorce proceedings and a query that obliterates any goodwill between separated spouses Barbara and Oliver Rose, played by Kathleen Turner and Michael Douglas. Five years after first starring together in 1984’s Romancing the Stone, Turner and Douglas ripped into the story of two people who go to increasingly outlandish lengths to keep each other from being happy—and suggest that there’s something else that could still be keeping them in the fight of their lives.

Waiting to Exhale

Release year: 1995

Director: Forest Whitaker

Notable cast: Angela Bassett, Whitney Houston, Loretta Devine, Lela Rochon

Any woman scorned by a split can find playful vindication in that meme of Angela Bassett strutting away from her husband’s torched car after learning of his deception—on New Year’s, no less. She’s able to find solace in her female friends, although two of them (Whitney Houston and Lela Rochon) continue to date married men themselves. By the end of the film, breakups abound for all the characters, and Bassett’s Bernadine gets exactly what she deserves: the promise of new love with a widowed civil rights attorney, yes, but also a hefty divorce settlement from her unfaithful ex.

In the Mood for Love

Release year: 2000

Director: Wong Kar-Wai 

Notable cast: Tony Leung Chiu-wai, Maggie Cheung

Looking to get your heart ripped from your chest, frame by frame? Try on this Wong Kar-Wai classic, in which Tony Leung and Maggie Cheung play neighbors who know they can never be together, but can’t stop themselves from exchanging long glances in rainy corridors whenever the mood strikes. After bonding over shared suspicions that their spouses are cheating on them, the pair falls in love themselves, but refuse to resort to the tactics of their partners by delving into infidelity themselves.

Eternal Sunshine of the Spotless Mind

Release year: 2004

Director: Michel Gondry

Notable cast: Jim Carrey, Kate Winslet, Tom Wilkinson, Mark Ruffalo, Kirsten Dunst

This Charlie Kaufman-penned film is a high-concept take on ending things—about a man so desperate to move on from heartbreak that he’s willing to wipe it from his subconscious. “I think the movie is so beloved because so many people can relate to knowing that something isn’t right, but loving so much and wanting to stay and wanting to figure it out and that cycle that can happen in the film,” Grande told Apple Music’s Zane Lowe of its resonance in her life. “I’m a massive Jim Carrey fan. I don’t know if you know this, but my first screen name was JimCarreyFan42. So I was definitely very young [when I first saw it]. It’s always been a favorite of mine.”

The Break-Up

Release year: 2006

Director: Peyton Reed

Notable cast: Jennifer Aniston, Vince Vaughn, Jon Favreau, Jason Bateman

When Brad Pitt blew up his marriage to Jennifer Aniston after meeting Angelina Jolie on the set of 2005’s Mr. & Mrs. Smith, his ex-wife responded in kind by making a 2006 comedy about breaking up with Vince Vaughn, whom she’d soon begin dating. The film was a lighthearted blockbuster about a Chicago couple forced to cohabitate in their shared apartment throughout their acrimonious parting. But much of the enjoyment comes from the headline-making backstory of it all, a juicy tabloid moment in the mid-2000s packed into a perfectly breezy date-night movie.

Forgetting Sarah Marshall

Release year: 2008

Director: Nicholas Stoller

Notable cast: Jason Segel, Mila Kunis, Kristen Bell, Russell Brand

While there are dozens of Bridget Jones-esque depictions of women working their way through a tub of ice cream and sob-singing to “All by Myself,” there are far fewer breakup narratives centered on blindsided men. That gets corrected with this 2008 blockbuster, which sees Jason Segel’s boy-next-door Peter in the throes of comical devastation after his girlfriend Sarah (Kristen Bell) ditches him for a dirty rockstar (Russell Brand). And when Peter decides to finally pry himself from his depressive state for a tropical getaway? Turns out his ex and her new fling are occupying the suite nearby.

(500) Days of Summer

Release year: 2009

Director: Marc Webb

Notable cast: Zooey Deschanel, Joseph Gordon-Levitt, Chloë Grace Moretz

Speaking of sad men, Joseph Gordon-Levitt’s greeting-card writer Tom (yes, that’s actually his job) is shattered when the manic pixie girl of his dreams (Zooey Deschanel’s Summer) shuts the door on their courtship. Bonding over The Smiths and bouncing on Ikea furniture can only sustain a couple for so long, Tom learns as the story of their relationship and inevitable split plays out. At least there’s Minka Kelly, as a woman named Autumn just waiting around the corner.

Blue Valentine

Release year: 2010

Director: Derek Cianfrance

Notable cast: Ryan Gosling, Michelle Williams

A year before making Take This Waltz, Sarah Polley’s twisted love triangle in which Michelle Williams’s character dismantles one relationship for another equally fractured tryst, the Oscar-nominated actor was already lovesick. In Derek Cianfrance’s directorial debut, she is Cindy to Ryan Gosling’s Dean—a pair of working-class dreamers who fall in love freely but grow resentful when they stay in their strained relationship for the sake of their child. The film switches between that present-day anguish and their blissful early days, asking us to perform a heartbreaking romantic autopsy.

Gone Girl

Release year: 2014

Director: David Fincher

Notable cast: Rosamund Pike, Ben Affleck, Carrie Coon, Neil Patrick Harris, Tyler Perry

This may be one of Anne Hathaway’s favorite romantic comedies, but it also serves as a deliciously deceptive breakup movie in the vein of 1987’s Fatal Attraction. Like Glenn Close’s character in that film, after a relationship goes sideways, Rosamund Pike’s Amy takes matters into her own hands. She doesn’t just leave her husband Nick (a perfectly smarmy Ben Affleck): She frames him for her alleged murder, giving a whole new meaning to the line, “If I can’t have him, no one will.” They may be back together by the movie’s end, but the once humdrum couple is irretrievably broken from its headline-making fallout.

Get Out

Release year: 2017

Director: Jordan Peele

Notable cast: Daniel Kaluuya, Allison Williams, LaKeith Stanfield, Bradley Whitford, Catherine Keener

While also not conventionally regarded as a breakup movie, there’s no denying that the terrifying events of Jordan Peele’s directorial debut culminate in the knowledge that Daniel Kaluuya’s Chris should run far, far away from his girlfriend, Rose (Allison Williams). What begins as a timely take on Guess Who’s Coming to Dinner, with Rose’s performatively liberal parents (never forget, they would’ve voted for Barack Obama’s third term if they could!) meeting her Black boyfriend for the first time, soon turns into an exceedingly necessary split.

Call Me by Your Name

Release year: 2017

Director: Luca Guadagnino

Notable cast: Timothée Chalamet, Armie Hammer, Michael Stuhlbarg

The tenderness of first heartbreak is best encapsulated in the film’s tearful one-take ending, in which Timothée Chalamet’s Elio begins to fully process the love he lost with Oliver (Armie Hammer) following their whirlwind summer romance. Chalamet’s mournful reckoning (later parodied by Drew Tarver’s Cary Dubek on The Other Two) seals the film’s central love story. But it’s the words from Elio’s father (Michael Stuhlbarg) that linger. “How you live your life is your business—just remember, our hearts and our bodies are given to us only once,” he says, reciting some of the words from André Aciman’s original novel. “And before you know it, your heart is worn out, and, as for your body, there comes a point when no one looks at it, much less wants to come near it. Right now, there’s sorrow, pain. Don’t kill it and with it the joy you’ve felt.”

Marriage Story

Release year: 2019

Director: Noah Baumbach

Notable cast: Adam Driver, Scarlett Johansson, Laura Dern, Alan Alda, Ray Liotta

After starring in Sofia Coppola’s Lost in Translation and Spike Jonze’s Her—widely interpreted as two opposing creative interpretations of Coppola and Jonze’s own breakup—Scarlett Johansson completed the unofficial trilogy with a leading role in Marriage Story. Thought to be Noah Baumbach’s cinematic rendering of his divorce from Jennifer Jason Leigh, Johansson plays Leigh’s proxy alongside Adam Driver, a wall-punching “Being Alive”–singing director with whom she’s engaged in a bitter custody battle over their young son. Not meta enough? Laura Dern’s character is rumored to be inspired by high-power divorce attorney to the stars Laura Wasser, who represented Baumbach in his 2010 divorce proceedings. In the film, she’s fighting for the opposite spouse.

Portrait of a Lady on Fire

Release year: 2019

Director: Céline Sciamma

Notable cast: Noémie Merlant, Adèle Haenel, Valeria Golino

In Céline Sciamma’s acclaimed film, portraitist Marianne (Noémie Merlant) and the betrothed woman she has been commissioned to paint, Héloïse (Adèle Haenel), are forced apart by the constraints of their 18th century love affair. But the film itself was born from the real-life romance, and subsequent split, between Sciamma and Haenel. “Just as the characters in the film discover each other in a painting studio, so Adèle and I met on a film set,” the director said in a 2019 interview. “We talked a lot about cinema [during our relationship] and we grew enormously intellectually. I also wanted to show that in the film: the lasting, emancipating effect that such a romantic encounter can have on your life.”

The Banshees of Inisherin

Release year: 2022

Director: Martin McDonagh

Notable cast: Colin Farrell, Brendan Gleeson, Barry Keoghan, Kerry Condon, Jenny the Donkey

Often, it is feckin’ friendship breakups that cut deepest of all. That idea is explored quite literally in Martin McDonagh’s Oscar-nominated film, which reunited his In Bruges leads Brendan Gleeson and Colin Farrell as two lads whose bond has been severed for reasons unbeknownst to the latter. What begins as a strained parting filled with stoic dismissals about growing apart devolves into all-out body horror, complete with chopped appendages. Parting can bring such sweet sorrow.

Past Lives

Release year: 2023

Director: Celine Song

Notable cast: Greta Lee, Teo Yoo, John Magaro

The Oscar-nominated feature debut from first-time filmmaker Celine Song delves into the often distressing question of what could have been. Nora (Greta Lee), a New York City–based playwright who moved to Canada from Korea when she was a child, reconnects with her childhood love, Hae Sung (Teo Yoo), years after first parting. Instead of rekindling their relationship (she is now married to John Magaro’s fellow writer Arthur), they find some form of resolution in the fact that their in-yun may have worked out differently in another life.