The Best Break-Up Movies, from ‘Casablanca’ and ‘Gone Girl’ to ‘Eternal Sunshine’

“Rebecca” (1940)

Just another reason why Alfred Hitchcock films should never be remade: The 1940 film “Rebecca” is devastatingly haunting. But the scariest part of the would-be ghost story is not that the titular dead Rebecca may be lurking in the halls; it’s that her housekeeper (Judith Anderson) just won’t shut up about her. Dump the guy, keep the ghost? Joan Fontaine stars as the new Mrs. de Winter who may have to fight for her life — and marriage.

“Casablanca” (1942)

Humphrey Bogart and Ingrid Bergman are starcrossed exes in the midst of World War II. It’s required viewing for any bawlfest, so whip out your matching fedoras and get ready to play it again, and again, and again. Try not to text “here’s looking at you, kid” to any former lover, though. 

“All That Heaven Allows” (1955)

Can two people really make it work, even if they’re from different backgrounds? Jane Wyman portrays Cary, a wealthy widow who is crushing on a younger man who is also her gardener, Ron (Rock Hudson). Despite falling in love, Cary dumps Ron after it’s clear her children disapprove. Yet she can’t stop thinking of their relationship, and eventually tries to take happiness in her own hands. But is it too late?

“Splendor in the Grass” (1961)

Natalie Wood and Warren Beatty star as two teens who want to get it on, but stop short out of fear of carnal sin. Much like “Footloose,” the film reminds viewers that the fun path not taken usually leads to a bleaker life. The closing lines from Woodsworth’s poem of the same name will leave you looking back on years (and relationships) past:  

“Though nothing can bring back the hour / Of splendor in the grass, glory in the flower / We will grieve not; rather find / Strength in what remains behind.”

“The Umbrellas of Cherbourg” (1964)

Jacques Demy’s gorgeous and heartbreaking musical operetta stars Catherine Deneuve and Nino Castelnuovo as Genevieve and Guy, two young souls deeply and madly in love. Sadly, their bliss doesn’t last long, and Michel Legrand’s legendary songs detail how their brightly colored fantasia is disrupted by the Algerian War and the disapproval of Genevieve’s mother. The film is a tribute to the power of first love — and an acknowledgement that it almost never lasts. 

“The Way We Were” (1973)

“You’ll never find anyone as good for you as I am, to believe in you as much as I do or love you as much,” Barbra Streisand says to Robert Redford in the classic 1973 film. We’re not sure if we’d say the same thing to someone who cheated on us, but damn does Hubbell (Redford) deserve to grovel for his former, complicated, curly-haired Katie (Streisand). At the very least, watch “The Way We Were” to know what exactly what Carrie Bradshaw (Sarah Jessica Parker) means in “Sex and the City” when she muses that there are two types of women in the world. Our parting words? “Your girl is lovely, Hubble.” 

“Modern Romance” (1981)

Not every break-up is permenant; as will-they-won’t they TV couples have proved, some people go through multiple break-ups before they tie the knot or leave each other for good. Albert Brooks’ “Modern Romance” makes an amazing neurotic comedy out of that type of toxic relationship, through the on-off relationship of Brooks’ movie editor Robert and Kathryn Harrold’s too patient for her own good Mary. As the indecisive and insecure Robert struggles to finish editing a sci-fi film, he waffles between breaking up and getting back together with an increasingly frazzled Mary, making for one of the most cringeworthy and funniest rom-coms of the ’80s.   

“Dirty Dancing” (1987)

“Is that a watermelon, or are you just happy to see me?” is a line we pretend was in “Dirty Dancing.” Part abortion drama (seriously, rewatch it), part sugar baby scandal, and 100 percent summer goals, “Dirty Dancing” remains a classic reason to visit the Catskills and learn how to get up close and personal on the dance floor. 

“Heathers” (1989)

It’s probably tempting to date a homicidal manic — especially if they look like Christian Slater circa 1989 — but killing your friends isn’t worth it. Shoulder-padded blazers and croquet games aside, “Heathers” walked so “Mean Girls” could run. But surely there must be a better way to deal with slut-shaming in high school? Winona Ryder is absolutely bulletproof as the conscience (?) of the black comedy. 

“When Harry Met Sally” (1989)

We hear you. “What? Break-up movie? Nah.” But the genius of “When Harry Met Sally” is that it transcends any categorization of being a typical love story. Sally (Meg Ryan) at first hates Harry (Billy Crystal), and they both fall in and out of love with other partners over the course of a decade. Heck, Harry even marries someone else and then gets divorced. Heartbreak is in fact what binds Harry and Sally together, and, with that, it’s a break-up film. Don’t at us. 

“Chungking Express” (1994)

Wong Kar Wai’s 1994 film gave us our heartbreak motto: “We’re all unlucky in love sometimes.” 

Filmed throughout the streets of Hong Kong, “Chungking Express” blends the unattainable and fantastical manic pixie dream girl motif with the femme fatale icon, played by Faye Wong, who leaves a shy beat cop (Tony Leung) with his head spinning. Find love in home invasions, the memory of a familiar tune, and dreamlike musings that compare leaving the tap running to an endless stream of tears.

“Swingers” (1996)

Your first thought after a break-up may be to want to get out there and meet someone new. “Swingers” will remind you that immaturity has no gender — so good luck in the dating pool! — and make you rethink re-entering the nightclub scene after seeing the ’90s Vegas strip. 

“Scream” (1996)

If Wes Craven’s “Scream” taught us anything, it’s that the boyfriend always did it. Pull out your film thesaurus to chart all the horror movie references as Sid (Neve Campbell) watches her pals get offed one by one. Try not to get distracted by an oddly-placed doggie door in a garage, swoon over Skeet Ulrich’s floppy hair, or compare Matthew Lillard’s perfectly psychotic performance to Shaggy. The “Scooby Doo” references end there, full stop.

“It’s literally like thinking of your first girlfriend,” Lillard told Vulture about revisiting the iconic film in honor of its fifth installment. “Looking back on this has been like looking back on the first love of your life.” 

“The First Wives Club” (1996)

Diane Keaton, Goldie Hawn, and Bette Midler make up the titular club, seeking revenge on the husbands who dumped them for younger women. Oh, and did we mention it’s the definition of an ensemble cast? Those exes are Dan Hedaya, Victor Garber, and Stephen Collins, while Sarah Jessica Parker, Elizabeth Berkley, and Marcia Gay Harden are the supposedly “other” women. Throw in Maggie Smith, Stockard Channing, Rob Reiner, and a Gloria Steinem cameo and we’re drawing up the divorce papers for a re-watch.

“Sliding Doors” (1998)

It’s a tale of two futures, two loves, and two very different hairstyles. Gwyneth Paltrow leads 1998’s “Sliding Doors,” about a woman who narrowly misses a train and sees both paths: the one where she makes it home in time to catch her boyfriend cheating, and one where she continues living an unfulfilled life. So, which future is preferred? Watch to see whether heartache is worth the pain. 

“High Fidelity” (2000)

Before Zoë Kravitz mulled over her exes in the short-lived Hulu series of the same name, sad sack Rob was played by John Cusack in the 2000 film adaptation of Nick Hornby’s novel. As a compulsive record store owner, Rob details his top five breakups. And yes, the story comes full circle with Lisa Bonet (aka Kravitz’s mother) playing the ultimate heartbreaker. 

“Bridget Jones’ Diary” (2001)

Oh dear Mr. Darcy (Colin Firth), how we lust after you so. Throw in Hugh Grant as a distraction, though, and things get a little more complicated for Renée Zellweger as Bridget Jones, a sarcastic Brit who is in love with her boss and dodging, “Why aren’t you married yet?” inquiries from family friends. We’ve been there, and while we haven’t shagged both Firth and Grant, we can still empathize with Bridget’s plight. 

“Legally Blonde” (2001)

The best way to get back at an ex is to better yourself, and Elle Woods (Reese Witherspoon) famously did just that by going to Harvard Law School. What, like it’s hard? Let “Legally Blonde” be your motivation to kick some ass, in the immortal words of Jennifer Coolidge’s beautician character. 

“Unfaithful” (2002)

Cheaters gonna cheat, and so Diane Lane escapes her posh suburban New York life — it really is a drag to be married to prime Richard Gere, apparently — and starts up an affair with an artist who lives in a dirty Soho loft. Her city double life is cut short after the romance leads to a deadly twist, proving that with every erotic thriller comes to the lesson that domesticity is key. Wrong! 

“Kill Bill Vol. 1” (2003)

There are probably easier ways to cancel a wedding than shooting a bride in the head. But when that bride is the Bride (Uma Thurman), we know that in lieu of a honeymoon, there will be a roaring rampage of revenge. The Bride sets out to slaughter her would-be baby daddy and ex Bill (David Carradine), who is also the leader of the Deadly Viper Assassination Squad and put a bullet in her head. Quentin Tarantino’s grindhouse samurai film doubles as a cathartic release for anyone who feels inclined to confront their former (toxic serial killer) lover. 

“Under the Tuscan Sun” (2003)

Post-divorce, Frances (Diane Lane) relocates from San Francisco to Tuscany and rebuilds an old villa (did you get the metaphor there?). During her “Eat, Pray, Love”-esque journey, Frances falls for a few men, but they’re just fleeting reminders that her one true love is herself. 

“Eternal Sunshine of the Spotless Mind” (2004)

Ever had that ex that you just want to erase forever? Well, so does Clementine (Kate Winslet), who completely excised former boyfriend Joel (Jim Carrey) from her memory. Written by Charlie Kaufman, the sci-fi psychological drama questions whether it really is best to have loved and lost, or if we are just better off not falling in love in the first place. Also, be ready to call your hairdresser to mimic Clementine’s many hairstyles. Who said you can’t find happiness in a new dye job?

“John Tucker Must Die” (2006)

After it’s discovered that high school hunk John Tucker (Jesse Metcalfe) is secretly dating multiple women, the jilted would-be exes band together for a top secret mission to publicly reveal John’s two-timing ways. Brittany Snow, Ashanti, Sophia Bush, and Arielle Kebbel star as the teen sleuths. Believe it or not, Penn Badgley plays John’s “nerdy” brother Scott. 

“Atonement” (2007)

Keira Knightley and James McAvoy bring it as a two hot young adults who burn for one another from afar. Leave it to Knightley’s onscreen sister, a very disturbing Saorise Ronan, to foil their affair and essentially ruin their lives across decades. 

“Lars and the Real Girl” (2007)

The lifeless sex doll in “Lars and the Real Girl” has a better romantic life than you do. And with Ryan Gosling, no less.

That’s it. That’s the caption. Now go cry. 

“Forgetting Sarah Marshall” (2008)

So not all (or any) of us would ever be so blessed as to date Kristen Bell and Mila Kunis, and yet, we still feel bad for Peter (Jason Segal) who suffers heartbreak at the hands of both women in this break-up flick.

“Maybe the problem is that you broke my heart into a million pieces and so my cock doesn’t want to be around you anymore!” Peter screams at his ex, Sarah. “Because you know what I just realized? You’re the goddamn devil!” And if that doesn’t resonate this Valentine’s Day, we don’t know what will.

A slew of hilarious supporting cast members including Russell Brand, Jonah Hill, Paul Rudd, and Bill Hader makes “Forgetting Sarah Marshall” the ideal antithesis to “When Harry Met Sally”: It’s another great love story, dissected. Also, it ends in a puppet Dracula musical, so it’s immediately iconic.

“An Education” (2009)

High schooler Jenny (Carey Mulligan) is seduced by the charming, older David (Peter Sarsgaard) and becomes part of the carefree, jetsetting class by proxy. Set in 1960s suburban England, the coming-of-age drama is based on journalist Lynn Barber’s memoirs, which makes the twist ending truly so much more hearbreaking. We can’t trust our hearts, it seems, even if we are desperate to. 

“(500) Days of Summer” (2009)

Joseph Gordon-Levitt falls for karaoke-singing, IKEA-shopping, record store–browsing Zooey Deschanel in this love letter to the quirky side of  the Los Angeles dating scene. To which we demand, “Where does that exist??!” Answer: Nowhere, because “(500) Days of Summer” is a projected fantasy that inevitably ends with the cold harshness of winter. 

“Blue Valentine” (2010)

Ryan Gosling and Michelle Williams are a devastatingly, achingly in love couple in Derek Cianfrance’s “Blue Valentine,” which premiered at the 2010 Cannes Film Festival. The film starts with the picture-perfect duo running away from their traumas, and opting instead to fall into each other, as an act of pure carnal desperation. Yet making out in alleys soon gives way to a stark, bleak future that involves money woes, raising a child, and perhaps discovering that love does not really conquer all. 

IndieWire’s review captured the flash-forward elements that answer what happens after you find your soulmate. “Can youthful idealism and love sustain itself long into adulthood?” the review asks. “Is it fair to even expect it to? ‘Blue Valentine’ asks, but is smart enough to know there isn’t an answer.” 

“The Five Year Engagement” (2012)

Jason Segel and Emily Blunt star as a couple whose prolonged engagement (it takes five years, hence the title) makes them question whether or not to walk down the aisle at all. Eventually, there is some form of a happy ending — it is a rom-com, after all — but not without first questioning what the point is of growing older alongside someone else.

“Celeste and Jesse Forever” (2012)

Celeste (Rashida Jones) and Jesse (Andy Samberg) want to be together forever, they really do. But after marrying young and watching life take them in opposite directions, the married best friends file for divorce — right as all their pals are getting engaged. “Celeste and Jesse Forever” is a close-up of ripping off that painful Band-Aid of a break-up, and second-guessing it all the way through.

“Silver Linings Playbook” (2012)

David O. Russell directs this tense movie about a dance competition and football bets. No, really. Jennifer Lawrence stars as a widow whose steps of grief include hooking up with her whole office (no shame, been there) and helping her new neighbor (Bradley Cooper) reunite with his ex. Spoiler: They fall in love instead. But is it just as toxic as their respective pasts, or are they meant to be? Destruction breeds destruction, after all. 

“Ruby Sparks” (2012)

A struggling literary would-be genius (Paul Dano) writes his perfect woman (Zoe Kazan), who magically comes to life. Yet because she’s one of his creations, aforementioned ideal woman has no thoughts of her own. Cue up the mansplaining and ego stroking, because “Ruby Sparks” has a distinct message about the male gaze, the idealization of feminity, and what it really means when self-important art too dangerously imitates life. Or is it the other way around? 

“Gone Girl” (2014)

Ah, to wonder what your partner is really thinking. That is, if you can’t just write their thoughts for them like in “Ruby Sparks.” 

David Fincher’s “Gone Girl” beautifully unspools the physical restraint it takes to not totally destroy one another in toxic relationships. “The primal questions of a marriage: What are you thinking? How are you feeling?” Nick Dunne (Ben Affleck) muses. “What have we done to each other? What will we do?” 

Turns out, what Nick’s wife Amy (Rosamund Pike) is willing to do is disappear, fake her death, and frame another one of her exes, played by Neil Patrick Harris. Crazy has never looked so cool, but we also don’t have to remind ourselves why we’re just fine being single and sane. 

“The Last Five Years” (2014)

An adaptation of the Off-Broadway musical, “The Last Five Years” tells the story of a five-year relationship between a rising novelist (Jeremy Jordan) and a struggling actress (Anna Kendrick). 

Jamie (Jordan) explains his side of the story in chronological order, while Cathy (Kendrick) revisits their romance in reverse. Fun fact: The characters do not directly interact, except for a wedding song in the middle where their timelines intersect. And like every great love story, “The Last Five Years” led to a real-life lawsuit from composer Jason Robert Brown’s ex-wife, Theresa O’Neill. 

“6 Years” (2015)

“6 Years” offers snapshots at a couple’s undoing ahead of their six-year anniversary. Hannah Fidell writes and directs, with Taissa Farmiga and Ben Rosenfield starring. Executive producers Mark and Jay Duplass also lend their signature heartfelt touch to the narrative, which culminates in two young adults coming to terms with what they each want for their futures. Turns out, forever is composed of tiny “nows,” and sometimes six years is a true lifetime for a love story.

“Blue Jay” (2016)

Mark Duplass and Sarah Paulson play former high school sweethearts who run into each other later in life, proving that love may actually have a second chance. Just in case you needed a break from your Kleenex.

“La La Land” (2016)

We really should be spacing out these heartbreaking Ryan Gosling films on Valentine’s Day, but let’s be real: You’re either going to rewatch “The Notebook” for the millionth time, or you’re going to need a reminder that love sucks (and also a little Emma Stone in your life doesn’t hurt). “La La Land” didn’t just invent jazz (cough, cough) and not win Best Picture at the Oscars; it also reunited “Crazy Stupid Love” co-stars Stone and Gosling. Or GoStone, if you will. Let the ridiculous freeway montage surprise you and fall in love with the beauty of being ill-fated lovers all over again. 

“Get Out” (2017)

Speaking of horrific exes, Allison Williams seems to have made a career off playing that girl. Marnie in “Girls” was merely a stepping stone to embody a privileged country club alum who solely dates Black men to trap her partners in a modern-day slave auction. Daniel Kaluuya deserves every single award for his haunting portrayal of an up-and-coming photographer who realizes he’s made a grave dating mistake. 

“Call Me by Your Name” (2017)

A whirlwind summer romance between a professor’s son (Timothée Chalamet) and a promising graduate student (Armie Hammer) might just be one of the greatest love stories of the past decade. So why are we recommending it to your poor heartbroken self? Strap in for lush Northern Italian landscapes, skinny dipping, and a seemingly never-ending take watching Chalamet break down in tears as the credits roll. It’s painfully accurate to our current state (and thank us later for that cathartic cry-a-long).

“Nappily Ever After” (2018)

“Love and Basketball” may be one of the great epic romance stories every told, but in “Nappily Ever After,” Sanaa Lathan instead plays a woman who is reeling from a breakup, not falling in love. Starting with a dramatic hair makeover, ad exec Violet (Lathan) undergoes a makeover from the inside, out, and realizes maybe she’s better off without the pressures of being the “perfect” partner after all. 

“The Pink Wall” (2019)

Writer-director Tom Cullen selected six moments of a six-year relationship between couple Leon (Jay Duplass) and Jenny (Tatiana Maslany) to highlight the fragility of any relationship. From gender expectations to balancing ambition with emotional comfortability, “The Pink Wall” will quietly make you crumble…in the best way possible. 

“Marriage Story” (2019)

A marriage between Scarlett Johansson and Adam Driver collapses, thanks to bicoastal living and a minor (…or major) indiscretion. Only watch Noah Baumbach’s domestic drama if you’re angry: The legal complications of even hiring a divorce attorney is enough to make you punch a wall. 

“Midsommar” (2019)

Accompanying your selfish and dismissive boyfriend to a mysterious Nordic retreat may not sound like the most romantic vacay (it isn’t), but perhaps seeing justice unfold by way of ancient torture devices will make you bearbeing near him. Oh, and you’re also the queen in this fantasy, with a very luxe floral crown and matching outfit. If you can stomach it, “Midsommar” will bring you more revenge satisfaction than you know. 

“Someone Great” (2019)

Jenny (Gina Rodriguez) has it all: two ride or die friends, a great new job worth moving across the country for, and a fantastic boyfriend…who wants to break up. The 2019 Netflix romcom celebrates best friendship at its finest, while still reminding us that even though not all breakups are amicable, time (and laughter) will heal all wounds. LaKeith Stanfield plays Jenny’s ex, with Brittany Snow and DeWanda Wise as her two besties.

“The Souvenir” (2019)

Joanna Hogg’s semi-autobiographical film, “The Souvenir,” premiered at the 2019 Sundance Film Festival, and later gave us the 2021 sequel “The Souvenir II.” A young film student becomes romantically involved with a charismatic but untrustworthy older man, and her artistic coming-of-age story unravels in the wake of a life-altering affair. 

“Portrait of a Lady on Fire” (2019)

The ultimate one that got away story, an artist (Noémie Merlant) is supposed to paint the wedding portrait of an heiress (Adèle Haenel) for her suitor. Yet the two women unexpectedly awaken a deep desire in each other, and their romance supercedes the impending nuptials to a man. You’ll laugh, you’ll cry, you’ll learn how to artfully angle a handheld mirror for your next Instagram selfie. 

“The Invisible Man” (2020)

Some may say “The Invisible Man” is a horror movie. Others will say it’s a psychological drama about reliving the trauma of escaping an abusive relationship. Or, we could just use it as a guidebook for how not to date. Rule one: No tech billionaires. Rule two: Don’t move to a secluded compound. Rule three: remember you can always cut through gaslighting tactics with a large butcher knife. 

“Birds of Prey” (2020)

We’ve all dated some sort of Joker, haven’t we? Margot Robbie leads an all-woman crew that takes back what’s rightfully theirs, after Harley Quinn (Robbie) tumultously breaks up with her controlling beau. Grab a bat and smash some shit, it’s time to confront our demons…and super-villian exes.

“The Banshees of Inisherin” (2022)

Not every break-up is a romantic one. Friendship break-ups can be even more devestating, and “The Banshees of Inisherin” is one of the few films to really capture the devestation and confusion that they leave behind. Colin Farrell’s sad eyed Pádraic’s desperate attempts to win back the affection of Brendan Gleeson’s solemn Colm is deeply relatable, even as their disagreement slowly devolves into a bitter blood feud.