Here lies the hopes and dreams of “happily ever after.” While we often go to the movies to see couples ride off into the sunset, it doesn’t always shake out that way. Across Hollywood history, there’s been tons of matches made in heaven, but right now we’re going to focus on those memorable break-ups we’re still not over, and may never get over. But hey, sometimes a truly great break-up in a film can be relatable, cathartic and as we'll see, really big break-ups can lead to even better results later on. Or, the break-up in and of itself is the happy ending. Either way, breakups are part of life, so let the tears pour for these ill-fated couples.
SPOILERS ahead!
Mia & Sebastian, La La Land
One of the best finales to a movie is arguably Damien Chazelle’s La La Land ending. After Emma Stone’s Mia and Ryan Gosling’s Sebastian fell in love in the musical comedy, their relationship ultimately falls apart after Mia is cast as the lead in a movie being shot in Paris. After Mia nails her audition, we catch the couple five years later, where both of them have found success in their fields, but are no longer together. In an emotional scene, Mia comes across Sebastian’s booming jazz club and he plays their song as the movie imagines what could have been if they stayed together.
Joel & Clementine, Eternal Sunshine Of The Spotless Mind
Eternal Sunshine of the Spotless Mind is not only one of the greatest breakup films out there, but the best movies of the 2000s, too. As we learn during the film, Kate Winslet’s Clementine decides to go through a trial procedure to forget her ex Joel after their breakup, which involves an argument that goes wrong regarding their thoughts about children. Within the movie’s apt meditation on breakups, the Eternal Sunshine ending has Joel and Clementine deciding to give each other another shot, knowing full well the outcome could play out the same between them this time.
Joe & Summer, (500) Days Of Summer
When (500) Days Of Summer opens, it warns its audience that they are not about to see a love story, but even so, it’s easy to still get swept up in the couple’s romance. While the 2009 movie is told through the eyes of Joseph Gordon-Levitt’s Joe, where he paints Zooey Deschanel’s Summer as the villain, the pairing operates as an interesting commentary on how people can idolize the other and ignore the signals that point to the other not being the right person for them. The breakup in this movie is sad, until Joe gets a poetic second chance with a woman aptly named Autumn.
Daniel & Miranda, Mrs. Doubtfire
Mrs. Doubtfire is one of the best Robin Williams movies, especially because of how it handles the realities of divorce. Throughout, the movie follows Williams’ Daniel as he disguises himself as a character named Mrs. Doubtfire in order to spend more time with his three children amidst his separation from Sally Field’s Miranda. Sadly, by the finale, the parents do not get back together. However, the breakup makes way for a sweet message for those who can relate.
Annette & Sebastian, Cruel Intentions
In 1999’s Cruel Intentions, Ryan Phillippe’s Sebastian breaks things off with Reese Witherspoon’s Annette in an especially emotional scene that leaves Annette by herself in absolute tears over him. The whole thing is the result of a bet Sebastian makes with Sarah Michelle Gellar’s Kathryn, where his winnings would be getting her in bed. But, once Sebastian goes to Kathryn to cash in, he learns she had been two steps ahead of him the whole time. This movie definitely lives up to its name!
Ted & Joanna, Kramer vs. Kramer
One classic breakup movie we’re not getting over anytime soon is Kramer Vs. Kramer, which centers on a couple’s divorce proceedings and how it affects their young son. Starring Meryl Streep and Dustin Hoffman as the couple, the drama brings a grounded perspective about how marriages can fall apart and how figuring out custody between parents can be a harrowing process.
Gale & Dewey, The Scream Movies
In between the scares of the Scream movies, a sweet romance blossomed between Courteney Cox’s journalist character Gale Weathers and David Arquette’s Deputy Dewey Riley. However, in 2022’s Scream, we learn that the couple split up due to Gale’s aspirations to live in New York City and Dewey’s substance abuse issues. What makes this breakup a real stab in the chest is when Dewey is killed off later in the movie.
Theodore & Samantha, Her
Can you fall in love with someone’s voice? That’s certainly true for Her’s Theodore (played by Joaquin Phoenix) once Samantha (Scarlett Johansson) comes into his life. He and the artificially intelligent virtual assistant hit it off during Spike Jonze’s critically acclaimed sci-fi film, but it’s not to be forever. In the end, Samantha chooses to join other AIs once her operating system seeks more knowledge outside of him.
Ennis & Jack, Brokeback Mountain
Ang Lee’s 2005 film Brokeback Mountain sees Jake Gyllenhaal’s rodeo cowboy Jack and Heath Ledger’s ranch hand Ennis falling in love in secret before leaving their relationship to live typical heterosexual lives with wives and kids. While they reconnect years after their first encounter, they never have a chance to really live happily with one another, and they have an especially tragic ending to their story by the time the movie concludes.
Han Solo & Leia Organa, The Star Wars Movies
One of the most iconic couples in movie history is Harrison Ford’s Han Solo and Carrie Fisher’s Leia Organa, who famously said the lines “I love you,” with “I know.” Unfortunately, when the Star Wars movies continued in 2015 with The Force Awakens, we learned that the couple had parted ways after having issues with losing their son Ben Solo to the Dark Side. Sadly, Han Solo also dies at the hands of Ben as well.
Dani & Christian, Midsommar
We’re not over this breakup in particular because of how traumatizing it is to experience! Ari Aster’s Midsommar tells the story of a couple, who are strained as is but their vacation to a Swedish midsummer festival really becomes the cherry on top of its demise. The festival is a front for a pagan cult recruiting and the couple cement their breakup when Christian is stuffed inside a bear and burned alive whilst Dani watches in horror and becomes the newest crowned member.
Rick & Ilsa, Casablanca
An especially classic breakup in cinema is the one between Humphrey Bogart’s Rick and Ingrid Bergman’s Ilsa at the end of 1942’s Casablanca. It’s about former lovers who reunite years after an affair. While one might expect their reunion to lead to the pair rekindling their love, Rick surprises Ilsa at the end of the movie by deserting her as she boards a plane because he feels she would be better off with her current fiancé.
Peter Quill & Gamora - Guardians of the Galaxy, Vol. 3
One of the sweetest couplings in the MCU once belonged to Chris Pratt’s Peter Quill and Zoe Saldana’s Gamora, who met during the events of the first Guardians of the Galaxy. Sadly for the pair, Thanos’ plot to destroy half the universe caused a major rift between them (quite literally) when Thanos sacrificed Gamora to get the Soul Stone. There seemed to be a silver lining for the couple in Vol. 3 when Gamora returned, but during the final Guardians of the Galaxy movie’s ending, the pair went down separate paths.
Celeste & Jesse, Celeste and Jesse Forever
2012’s Celeste and Jesse Forever is a rather ironic title considering Rashida Jones’ Celeste and Andy Samberg’s Jesse don’t get a happily ever after. The movie is about high school sweethearts who marry young and decide to separate years later. Despite their separation, the former couple insist on remaining best friends, making for some funny and rather awkward situations between them. Ultimately, the couple need to let go and move on from each other.
Gary & Brooke, The Break-Up
After Jennifer Aniston had starred in numerous romantic comedies over the years, the Friends actress changed things up with 2006’s The Break-Up alongside Vince Vaughn. The comedy follows a longtime couple that decides it's not working between them but refuses to move out of their condo. A lot of funny things go down when they become roommates following the breakup. While it could have been a setup for a sweet rekindling, they ultimately stay broken up.
Oliver & Elio, Call Me By Your Name
Call Me By Your Name is about 17-year-old Elio (Timothée Chalamet) who meets a handsome doctoral student Oliver (Armie Hammer) while spending the summer in Italy in 1983. The pair strike up a passionate love affair over the course of the sunny months, but sadly for Elio, it was only a fling. At the end of the film, Elio sits tearfully by the fireplace in winter as he learns Oliver has since become engaged.
Nora & Hae Song, Past Lives
Past Lives, which was such a powerful 2023 movie that it became one of the 2024 Oscar nominees for Best Picture, is about two childhood friends who cross paths on multiple fronts throughout their lives. Greta Lee plays Nora, a Korean woman who has to say goodbye to her best friend Hae Song (Teo Yoo) as a kid when her family immigrated to New York. As adults, Hae Song visits Nora in the Big Apple, after she’s already been married. There’s a sense that the couple missed out on something special, but as the ending illustrates, they’ll have to perhaps wait for their next life to see their lives align.
Rhett & Scarlett, Gone With The Wind
One of the most tragic love stories in cinema is certainly 1939’s Gone With The Wind between Clark Gable’s Rhett Butler and Vivien Leigh’s Scarlett O’Hara. With the backdrop of the Civil War behind it, the sprawling epic brings together Rhett and Scarlett during the war’s dire circumstances, leading to their marriage and the birth of their daughter Bonnie Blue. However, when Scarlett’s initial crush Ashley comes between them, Rhett leaves her under the morning fog glow and she is heartbroken.
Noah & Allie, The Notebook
A particularly sad breakup in the movies comes via 2004’s The Notebook. When the movie begins, two teens, Allie and Noah (Rachel McAdams and Ryan Gosling) from the opposite side of the tracks fall in love. However, Allie’s parents put a rift between them and they don’t see each other for years. Little does Allie know that after their breakup, Noah wrote to her every day for an entire year and her mother kept them from her. Lucky for this romance, it ends in a happy (yet very bittersweet way) down the road.
Jerry & Dorothy, Jerry Maguire
In 1996’s Jerry Maguire, which is one of Tom Cruise’s best performances ever, the actor’s character of Jerry and Renée Zellweger’s Dorothy have an incredibly grounded and quite sad breakup scene when they realize they don’t want the same things anymore. The sequence really tugs at the heartstrings because Jerry had started to bond with Dorothy’s young son Ray since their marriage.
Alice & Dan, Closer
In 2004’s Closer, Jude Law’s Dan leaves Natalie Portman’s Alice heartbroken when he confesses he’s been cheating on her. As she protests the breakup, he admits he’s “selfish” as she cries in his arms. She asks him to make tea, but while he’s preparing it she jets out the door and he never sees her again.
Nicole & Charlie, Marriage Story
Breakups are always more difficult when children are involved. In 2019’s Marriage Story, audiences get a chance to see the pitfalls that come with divorce as a successful theater director Charlie (Adam Driver), and his wife and actress Nicole (Scarlett Johansson) go through the motions of ending their marriage.
Bernadine & John, Waiting To Exhale
In 1995’s Waiting To Exhale, Angela Bassett’s Bernadine, who is the mother of two kids, has spent much of her adult life shelving her career aspirations to raise her children. So we really feel the sting when she finds out that her husband of eleven years has been cheating on her with his bookkeeper and plans to divorce her. Of course, Bernadine gets her revenge by sending her ex’s car up in flames.
Peter & Sarah, Forgetting Sarah Marshall
Sometimes the worst breakups are about the timing of it all, and we’re definitely not over this super awkward one in Forgetting Sarah Marshall. In the 2008 comedy, Kristen Bell’s Sarah dumps her longtime boyfriend Peter (Jason Segel) while he’s butt naked in their apartment. Then, they both run into each other in Oahu where Peter runs into Sarah and her new man, Aldous (Russell Brand). It’s funny as a movie, but gosh this is a nightmarish scenario!
Danny & Debbie, About Last Night
In the 2014 movie, Michael Ealy and Paula Patton’s Danny and Debbie relationship blossoms and then falls apart during the movie’s runtime. It all comes to a head during a New Year’s Eve party that leads Debbie to move out. Thankfully, in the case of this movie, the pair do makeup by the end of the film!
Katie & Hubbell, The Way We Were
1973’s romantic drama The Way We Were, had Barbra Streisand and Robert Redford playing lovers amidst their experiences with the House Un-American Activities Committee. Despite their differing opinions, they fall for each other, get married, and have kids. Their different beliefs ultimately drive them apart, but at least they get an epic kiss goodbye at the end.
Dean & Cindy, Blue Valentine
Marriage is hard work. In 2010’s Blue Valentine, Michelle Williams and Ryan Gosling depicted a rather grounded couple’s story in a narrative that impressively plays with timelines. The working-class romance is a tragic one that puts the spotlight on how ego can be the pitfall of a once passionate love.
Emma & Adele, Blue Is The Warmest Color
French award darling Blue Is The Warmest Color had us messed up following watching Léa Seydoux and Adèle Exarchopoulos’ Emma and Adèle fall in love only to fall apart. The 2013 movie follows the two women across many years as they become closer, only for some major blemishes in their relationship to lead to an emotional breakup that changes them forever.
Julianne & Michael, My Best Friend’s Wedding
There’s something romantic about marrying your best friend, as Julia Roberts’ Julianne hopes to do during My Best Friend’s Wedding, but her motivations are so crossed. Throughout the movie, she tries to break up Dermot Mulroney’s Michael with Cameron Diaz’s Kim, but ultimately she realizes Michael is not the one for her. It’s still a sweet wedding as another one of her BFF’s surprises her at his wedding and they dance the night away.
Su & Chow, In The Mood For Love
There’s nothing quite like the romantic tension that Maggie Cheung and Tony Leung created in 2000’s In The Mood For Love. The movie is about two Shanghainese expatriates Su and Chow, who are already married, but fall into an emotional affair with one another as they learn of each being cheated on by their spouses. However, the tension never explodes into the affair we want it to as the movie ends with Chow confessing his love in a hole in a temple wall rather than to Su.
Ben & Janine - He’s Just Not That Into You
He’s Just Not That Into You is one of those romantic comedies that follows a series of intertwined couples played by A-list actors. The most cutting arc in the movie is perhaps as Jennifer Connelly’s Janine realizes her husband Ben (Bradley Cooper) has been cheating on her with his yoga instructor Anna (Scarlett Johansson) amidst her slaving over house renovations for their place. After a particularly awkward moment between Ben, Janine, and Anna, Janine figures it all out and sends Ben packing.
Evan & Kayleigh - The Butterfly Effect
In 2004’s science fiction thriller, The Butterfly Effect, Ashton Kutcher plays Evan, a man who learns he can travel back in time and alter the past, present, and future. Sadly for Evan, as he discovers this power, he is met with the reality that his love Kayleigh (Amy Smart) often has traumatic fates if he is with her. By the end of the movie, he has to use his powers to make sure they are not together and she never even knew him. What could be worse than a breakup that the other person doesn’t even know about or experienced?
So much heartbreak!! To keep it rolling, check out the TV breakups we're not over yet next!
