Top 10 Saddest "One That Got Away" Movie Endings
#10: Ann & Joe
Roman Holiday (1953)
Its a tale as old as time: a beautiful princess sneaks away from her responsibilities for a day, meets an ordinary guy, and falls in love. Unfortunately for Gregory Peck, theres no genie in this movie to turn him into a prince. After a day full of adventure and romance, Ann has to return to her royal duties and her home country so the two must say goodbye. After she walks away, the look on Joes face says it all. Hes hoping shell change her mind and come back, but the tears in his eyes tell us that he knows deep down it wont happen. Their love might have only lasted 24 hours, but it was the real thing.
#9: Will & Viola
Shakespeare in Love (1998)
This period film revolves around a fictionalized version of William Shakespeare, who falls in love with an upper class woman as hes writing Romeo and Juliet. Viola is obsessed with the theater, and just like Princess Ann, she sneaks away from her cushy life to spend time with the commoners. However, Viola is already betrothed to a nobleman who plans to take her with him when he moves to the New World. She and Will have spent nearly every day together over the last several weeks, living in a fantasy that neither wants to leave. But reality soon comes crashing back. Parting is such sweet sorrow.
#8: Guy & Girl
Once (2007)
This low-budget Irish musical only had a limited theatrical release in North America, so it wasnt on many peoples radar. Theres no flashy costumes or set pieces just two musicians who bond over their shared passion. They spend a week together playing music and writing songs. Their connection is deeply intimate, but nothing physical ever happens between them. Eventually, Guy learns that this is because Girl is married, and shes decided to reconcile with her husband. Their parting is less dramatic than most on this list, but that doesnt make it any less devastating. Their relationship is a classic case of right person, wrong time.
#7: Katie & Hubbell
The Way We Were (1973)
Its actually amazing that these two opposites made it work as long as they did. Katie is a strong-willed political activist, while Hubbell is happy-go-lucky and popular with the ladies. They meet at college in the late 1930s, then reunite after Hubbell returns from the war. Their love is strong, but their relationship is rocky because they simply cant overcome their differences. They break up, get back together, and eventually get married, but it doesnt last long. Were rooting for these crazy kids the whole time, but its clear that theyll both be happier if they forge their own paths.
#6: Mia & Seb
La La Land (2016)
This film takes the typical Hollywood musical happy ending and flips it on its head. Mia and Seb seem made for each other. They have obvious chemistry and similar struggles in their careers, and theyre both fabulous dancers. In the end, though, they decide to pursue their dreams separately, rather than try to make things work together. The final montage, which shows what might have been, is heartbreaking. They may have made the right choice for themselves and their careers, but can they truly say they have no regrets? Success must feel bittersweet when it comes at such a cost.
#5: Yuri & Lara
Doctor Zhivago (1965)
Considered to be one of the greatest films ever made, this epic romance follows the titular character, Yuri Zhivago, through two wars and the Russian Revolution. Along the way he marries Tonya, whom hes known since childhood. But while hes stationed at a field hospital during World War I, he meets and falls in love with a nurse named Lara. As the years pass, violence and political upheaval tear Yuri and Lara apart, then bring them back together, over and over. Ultimately, Lara is forced to flee Russia for her own safety, while Yuri stays behind. Omar Sharif turns in an understated yet powerful performance as Zhivago, a man who constantly finds himself at the mercy of forces beyond his control.
#4: Chow & Su
In the Mood for Love (2000)
Hong Kong director Wong Kar-wais gorgeous masterpiece tells the story of two neighbors who discover that their spouses are cheating on them with each other. While their partners are out of town, Chow and Su begin spending more time together and eventually realize theyre falling in love. However, they refuse to act on their feelings, believing it would be wrong. Watching these two pine for each other while only a thin wall and their own sense of decency separate them is more than just sad its agonizing. This intimate drama paints a brutally realistic picture of the pain of longing.
#3: Marianne & Héloïse
Portrait of a Lady on Fire [aka Portrait de la Jeune Fille en Feu] (2019)
They know their love is doomed from the start, but the few days they have together are filled with a passion that theyll probably never know again. Set in the late 1700s, the film follows Héloïse, whose mother is trying to marry her off to a noble, and Marianne, who has been hired to paint Héloïses portrait. The two are immediately drawn to each other, but of course, in this time period, a relationship between two women is impossible. Watching them discover their true selves together, all while knowing they have no chance at a future, is gut-wrenching.
#2: Rick & Ilsa
Casablanca (1942)
Rick Blaine and Ilsa Lund shared a brief but intense romance in Paris before circumstances tore them apart. Their reunion at Ricks nightclub in Casablanca at the height of World War II rekindles that profound connection, offering the tantalizing possibility of making a life together. However, Ilsa is married to a heroic resistance leader whose work is vital to fighting the Nazis. Eventually, Rick has to make the hardest decision of his life: let Ilsa stay with him in Casablanca, or help her escape with her husband. You already know which he chooses. Rick makes the ultimate selfless sacrifice, recognizing that the fight for freedom outweighs everything else.
Before we unveil our top pick, here are a few honorable mentions.
Guy & Geneviève, The Umbrellas of Cherbourg [aka Les Parapluies de Cherbourg] (1964)
Another Couple Torn Apart by War, Theyre Forced to Rebuild Their Lives Separately
Edward & Kim, Edward Scissorhands (1990)
Romance Is Especially Difficult When One Partner Has Scissors for Hands
Stevens & Sally, The Remains of the Day (1993)
This Solemn English Butler Cant Open Up Long Enough to Admit His Feelings
Gil & Adriana, Midnight in Paris (2011)
He Travels to the Past to Meet Her, but Eventually Realizes He Belongs in His Own Time
Elio & Oliver, Call Me by Your Name (2017)
It Might Be Young Love, but That Doesnt Make It Any Less Heartbreaking
#1: Jack & Ennis
Brokeback Mountain (2005)
Like Marianne and Héloïse, Jack and Ennis are kept apart by societys rigid boundaries. They meet while working together in the remote Wyoming wilderness. Though Ennis is quiet and reserved, their relationship soon turns into a passionate affair. Jack dreams of getting a place together, but deep down they both know its all but impossible. Over the years, theyre only able to steal a few fleeting moments together, and they have to keep them secret at all costs. If they had been born in a different place or a different time, their story could have had a much happier ending.
Which of these tragic love stories left you in tears? Let us know in the comments.