Some of the most memorable movie romances aren't the ones with the happy endings; they're the melancholy tales that rip your heart out and have you reaching for the tissues. These depressingly doomed pairings have left us swooning, crying, and then feeling a little better about being single. Since the happily-ever-after movies get all the attention this time of year, we thought we'd look back on some of the saddest love stories ever told with our definitive list of the most heartbreaking movie couples of all time. (Warning: there are MAJOR SPOILERS ahead.) And for more reasons to cry, revisit The Saddest TV Episodes of All Time.
1 | Noah and Allie, The Notebook (2004)
New Line CinemaYes, Noah and Allie do eventually get together after years of enduring the kind of romantic impediments that only Nicholas Sparks can write. But the movie ultimately reveals that the elderly woman being told the story is Allie, no longer able to remember Noah as a result of her dementia, so you end up weeping anyway.
2 | Jack and Rose, Titanic (1997)
Paramount PicturesWe can debate endlessly whether Rose could have saved Jack by making room on that piece of wooden debris, but it's far more tragic the way it turns out. Rose is forced to say goodbye to her one true love—and despite their brief time together, she remembers him for the rest of her long life.
3 | Robbie and Cecilia, Atonement (2007)
Universal PicturesThe twist at the end of Atonement is a gut-punch: Robbie and Cecilia are never able to reconcile. Instead, after being cruelly torn apart, they both die separately during the war, without being able to reunite. No wonder a guilt-ridden Briony concocted a happier conclusion.
4 | Seb and Mia, La La Land (2016)
LionsgateFor much of La La Land's run, Seb and Mia have the kind of romance that seems to only exist in movie musicals—that is, there's a fair amount of singing and dancing. But reality creeps in, and by the end, the only way this ill-matched pair can be together is in a bittersweet fantasy sequence that serves to underscore what they've lost.
5 | Rick and Ilsa, Casablanca (1942)
Popperfoto / Getty ImagesIf Shakespeare gave theater the ultimate star-crossed lovers story with Romeo and Juliet, Casablanca may be the definitive cinematic equivalent. Forcing Ilsa to get on a plane and leave him behind for good, Rick promises her regret if she stays, uttering the iconic line, "Maybe not today, maybe not tomorrow, but soon and for the rest of your life."
6 | Ally and Jackson, A Star Is Born (2018)
Warner Bros. PicturesIf you've seen any iteration of A Star Is Born, you know how this doomed love affair ends. But in the most modern adaptation, Bradley Cooper—as both director and star—delivers one of the most haunting versions of a troubled addict who fears he is holding his wife back. And Lady Gaga turns in a heartbreaking performance of grief for the man she loved.
7 | Tish and Fonny, If Beale Street Could Talk (2018)
Annapurna PicturesThe strength of If Beale Street Could Talk, based on the James Baldwin novel, is in its tender portrayal of the love between Tish and Fonny, which deepens the tragedy of the pair being torn apart by a false accusation and a corrupt legal system.
8 | Geneviève and Guy, The Umbrellas of Cherbourg (1964)
20th Century FoxWhether in French or in English, the haunting anthem "I Will Wait for You" has brought tears to the eyes of so many who have fallen under the spell of this lush musical romance. The knowledge that Geneviève and Guy don't end up together makes it that much harder to endure.
9 | Jack and Ennis, Brokeback Mountain (2005)
Focus FeaturesWhile it became something of a pop culture punchline, "I wish I knew how to quit you" is a truly stirring declaration of love. It's easier now to imagine a world where Ennis and Jack could actually be together, but they're victims of their time and circumstances, as Brokeback Mountain's gutting ending reminds us.
10 | Laura and Alec, Brief Encounter (1945)
The Samuel Goldwyn CompanySo many of the romances on this list are doomed by timing, and Laura and Alec's is one of the most poignant of them all. In this beloved classic, the pair's almost-affair is limited to what the title suggests—a brief encounter—even though it's clear to both of them that it could have become something so much more substantial.
11 | William and Viola, Shakespeare in Love (1998)
Miramax FilmsThe ending of Shakespeare in Love is not a tragic one: Viola is able to escape what would have been a loveless marriage, and she inspires the titular playwright's Twelfth Night. But for anyone hoping that these two crazy 16th-century kids could make it work, it's certainly a bittersweet conclusion. And for more Oscar winners to remember, here are 11 Academy Award Best Picture Winners That Still Hold Up.
12 | Christian and Satine, Moulin Rouge (2001)
20th Century FoxWhen someone is coughing blood into a handkerchief in a period piece, it's a fairly safe assumption that her story won't end well. So yes, Christian and Satine do finally find their way to each other, declaring their love for one another in the purest way imaginable: belting pop songs. And then Satine dies in Christian's arms, and we reach for the tissues.
13 | Chow and Su, In the Mood for Love (2000)
Criterion CollectionIn Wong Kar-wai's gorgeous In the Mood for Love, there is an extramarital affair—but it's the protagonists' respective spouses who are breaking their marriage bonds with each other. Chow and Su, on the other hand, repeatedly just miss the opportunity to be together, leaving their romance tragically incomplete. And for more great movies from the last two decades, find out The Best Movies of the 21st Century, According to Critics.
14 | Molly and Sam, Ghost (1990)
Paramount PicturesGhost is widely remembered for the most sensual use of a pottery wheel ever committed to film, but the sad truth is, a widow and her dead husband can't end up together—no matter how much they love each other. And now just hearing "Unchained Melody" makes us misty.
15 | Hazel and Gus, The Fault in Our Stars (2014)
20th Century FoxJohn Green's novel The Fault in Our Stars helped usher in a new age of weepy teen romances. This film adaptation certainly kept the tears flowing, with Shailene Woodley and Ansel Elgort taking on the roles of two young people who meet in a support group for cancer patients. Needless to say, their love story takes a tragic turn. And for more memorable teen movies, discover The Best Teen Movie That Came Out the Year You Graduated.
16 | Joel and Clementine, Eternal Sunshine of the Spotless Mind (2004)
Focus FeaturesIn Eternal Sunshine of the Spotless Mind, Joel and Clementine's relationship is already over when the movie begins. But this sci-fi romantic drama offers an innovative, non-linear exploration of falling in and out of love—and why sometimes it's easier to forget the pain of heartbreak than live with it.
17 | Esther and Norman, A Star Is Born (1954)
Warner Bros. PicturesThe Judy Garland-James Mason A Star Is Born does not end more happily than the Lady Gaga-Bradley Cooper version. It did, however, introduce the song "The Man That Got Away," which has gotten lovelorn listeners through many lonely nights.
18 | Landon and Jamie, A Walk to Remember (2002)
Warner Bros. PicturesBefore there was John Green, Nicholas Sparks had a long career of making us cry with romances in which one character dies. A Walk to Remember may not be the perfect film you remember it being when you were a maudlin teen, but listening to Mandy Moore sing "Only Hope" will never get old. And for another walk down memory lane, check out The Biggest '90s TV Teen Idols, Then and Now.
19 | Dean and Cindy, Blue Valentine (2010)
TWCIn many ways, Blue Valentine is an anti-love story, making it the worst possible movie to watch on the holiday that gives the film its title. Still, Ryan Gosling and Michelle Williams turn in two exceptional performances as a couple whose passionate romance curdles into toxicity. And for more entertainment content delivered straight to your inbox, sign up for our daily newsletter.
20 | Benjamin and Daisy, The Curious Case of Benjamin Button (2008)
Paramount PicturesHollywood's most famous star-crossed lovers tend to simply be in the wrong place at the wrong time, which is particularly true of the title character and Daisy in The Curious Case of Benjamin Button: She's aging normally, while he ages backwards. While they do eventually meet in the middle, their love can't last—and by the end, Daisy has grown old and Benjamin has become an infant, a tragic inevitability.
21 | Guy and Girl, Once (2007)
Buena Vista InternationalThe central characters in Once don't even have names, which only reinforces how fleeting they are in each other's lives. They can't really be together—they have their own respective relationships to sort out—and they never truly try, but the passion and pathos in the music they create together suggests that they could have had a great love story.
22 | Tony and Maria, West Side Story (1961)
Donaldson Collection / Getty ImagesWe've already mentioned Romeo and Juliet, and Shakespeare's classic has been adapted to the screen over and over again. One of the most memorable versions, however, is the film adaptation of the musical West Side Story, in which the original play is given a modern twist. Sadly, things don't end any better for Tony and Maria.
23 | Cathy and Jamie, The Last Five Years (2014)
Radius-TWCWe know Cathy and Jamie won't end up together: The movie ends with her singing "Still Hurting" about their breakup. But the tragedy of The Last Five Years is the way it plays out—as their five-year relationship is told from start to finish for Jamie, it's told in reverse for Cathy, making it so they're never on the same page, and we have to see them fall apart twice. And for the onscreen relationships that sparked offscreen magic, check out these Onscreen Couples You Totally Forgot Dated in Real Life.
