Breaking up is tough. People build their lives around each other, thinking their love will last forever, and then someone changes their mind. Spouses cheat, tell lies, and break each others hearts, proving the “Happy Ever After” fairy tale ending to be nothing more than a temporary stopgap. When someone has their world shaken in this way, they believe that nobody has ever experienced anything close to the pain and suffering they’re currently going through — but they’re wrong. Everybody gets their heart broken, and it happens all the time. They say that “life is pain,” and the same is true for love; just about everyone has to deal with it, and hardly ever does it end in anything but loss and bitterness. Regardless, we keep on searching for it.
The movies on this list aren’t love stories. Although long held as a universal theme, thousands of years of humanity have taught us that love does not, in fact, conquer all. Love fades, but life goes on. These films are about survival after a failed romance. Self-respect, inner fulfillment, and forgotten friends can often only be re-discovered after dealing with a break up. The movies on this list prove there’s more to life than romantic love, which so often proves to be a mere illusion, anyway.
Here’s 15 Essential Post-Breakup Movies. Be wary, for there will be spoilers for many of these films.
15. Private Benjamin
Goldie Hawn was nominated for an Oscar for her role as the title character in Private Benjamin; the film is romantic and comedic, though it is a major disservice to dismiss this 1980 masterpiece as just another “romantic comedy.” After the worst wedding night ever (which we dare not spoil here), young Judy Benjamin, in an effort to bring structure into her life, decides (or rather, she is tricked by Harry Dean Stanton) to join the army. She immediately hates it and tries to leave, but eventually acclimates and finds herself legitimately independent for the first time in her life. Eventually, she finds love with a handsome French doctor, played by Armand Assante, and is ultimately forced to choose between her military career or a seemingly storybook romance.
Romance isn’t all it’s cracked up to be, however, and Private Benjamin is legendary for subverting the fairy tale love story the film seemed to be building towards. Judy ultimately realizes that her would-be Prince Charming is actually kind of a jerk, and she is better off leaving him and respecting herself, rather than becoming a mere prize for some wannabe patriarch. A woman doesn’t need a man to experience a full life, or vice-versa; happiness doesn’t come from servitude, but from living independently.
14. The Odd Couple
While people sometimes get distracted by romance, true companionship isn’t necessarily found in someone who one wants to kiss and make love to, but, rather, in your best friend. Felix Ungar and Oscar Madison may have been unlucky in love, but at least they had each other. The Odd Couple is the story of anal neat freak Felix; after being dumped by his wife, he moves in with Oscar, a slovenly fellow divorcee. Together, they make an unlikely and endearing pair of pals.
The Odd Couple, based on the play by Neil Simon (who also wrote the film), stars Jack Lemmon and Walter Mathau as Felix and Oscar, respectively, with Mathau reprising his role from the play (Felix had been played by the great Art Carney of The Honeymooners on the stage). The play and film are notable for treating the leads almost like belligerent lovers. Friendship is like romance, only more pure and genuine — because nobody is trying to sleep with each other.
The Odd Couple was adapted into a long-running TV sitcom starring Tony Randall and Jack Klugman as Felix and Oscar, and, in 1998, a full 30 years after the original film, Lemmon and Mathau reunited for Neil Simon-penned The Odd Couple II, which was way better than it had any right to be.
13. Blue Valentine
There’s nothing wrong with getting married. Many men and women find one partner whom they can adore for their entire lives; they can make a beautiful home for themselves, have children, and carry out fulfilling lives, in a partnership founded by mutual love and respect. Indeed, that is what a modern marriage is supposed to be. Unfortunately, this is all-too-often not the case.
Blue Valentine is the story of love, from its sweet beginnings, to its bitter end. Brilliantly cutting between romantic youth and jaded maturity, the film in brutally intense in its depiction of failed romance, in which the person you fall in love with is, and isn’t, the same person once things turn sour. When a relationship becomes toxic, what can a couple do? It becomes especially heartbreaking considering there’s an innocent (and adorable) child involved. Blue Valentine is probably the most difficult film on this list, a motion picture memorial to the most painful of heartbreaks.
12. Scott Pilgrim vs The World
Scott Pilgrim vs The World, based on the hit comic book by Bryan O’Malley, didn’t do so well at the box office, but instantly became a cult classic with its video game-inspired aesthetic, all-encompassing sense of humor, all-star cast, and audaciously innovative action sequences.
In Scott Pilgrim, the titular hero tries to defeat his enemy with the Power of Love, but fails. After using an extra life to take another crack at “the boss,” Scott eschews the Power of Love and instead fights using the Power of Self-Respect, leading to an uncontested victory. This is one of the few movies on our list in which the hero “gets the girl” in the end, though it’s wide open if the two would-be soul mates have any kind of long-term future together. Still, it’s important to remember that Scott doesn’t win because he wants the girl, the prize at the end of the finish line. He wins because, while romantic interests come and go, one can never break up with oneself.
11. An Unmarried Woman
The divorce rate in The United States is insanely high, yet people keep on buying into the dream of marriage and how saying “I do” will make everything all right, forever. Unfortunately, “Happily Ever After” often has an expiration date. In An Unmarried Woman, Jill Clayburgh’s Erica reaches hers when she discovers her husband is cheating on her with a younger woman. Erica’s whole world is shattered and she suddenly finds herself alone in the big city…
Time for sex! Indeed, Erica, now sans-husband, is free to experience the kind of sexual freedom that could only have been so intimately showcased in 1978 at the height of the progressive feminist movement. Of course, the film is a whole lot more than an R-rated sex romp, and it was nominated for three Academy Awards, including Best Actress and Best Picture.
10. Legally Blonde
In Legally Blonde, Reese Witherspoon plays Elle Woods, who follows her ex-boyfriend to Harvard in an effort to win him back, but quickly learns that there’s more to life than getting married to a hot guy. She actually turns out to be one hell of a lawyer, and finds herself striving, rather than struggling, in the notoriously difficult world of law and order.
Elle is a product of her privileged upbringing, and her ultimate goal is to be a married fashionista who makes lots of babies for her man. Once she removes herself from the societal standards which had been dictating her entire life, she emerges as a powerful lawyer, while still maintaining her perfect fashion sense and bubbly personality.
The message of the film is that love should not be pursued as requirement for admission to society; it’ll just happen in its own time. Chasing guys or girls just isn’t worth it. If someone dumps you, that means they don’t deserve you. Plus, Warren was a complete tool, anyway.
Speaking of Reese Witherspoon’s, we look to Fear, which was also Mark Wahlberg’s first leading role in a feature film. Reese plays a young teenager, Nicole, fostering a mild rebellious streak who falls for the quintessential bad boy, David, played by Marky Mark. He’s from the wrong side of the tracks, but is her dream guy…until they break up, at which point David is revealed to be a total psycho stalker with murderous intentions. Drama, home invasion, and an ass-kicking turn by CSI’s William Petersen ensue.
The reality can never quite live up to the fantasy one cultivates in their head. Nicole thought she loved David, but he turns out to be a monster. Not everyone’s exes become literal psycho killers, but the sentiment remains that if somebody who seems too good to be true turns out to be not worth it, then they can become toxic. It’s always best to maintain maximum distance from bad influences, especially those of the romantic/mass-murdering variety.
8. The Graduate
Like Scott Pilgrim vs The World, The Graduate is a film in which the hero gets the girl at the end. Unlike Scott, however, young Ben Braddock never finds the self-respect he so desperately needs, and his quest to win the girl, though successful, is immediately revealed to be a shallow and meaningless victory.
Dustin Hoffman plays Ben, a young and directionless kid who has just finished college, but is too lazy to even apply to grad school. He drifts through life wallowing in self-pity (to an admittedly rockin’ Simon & Garfunkel soundtrack) and aimless oblivion. His parents try to set him up with young Elaine Robinson, though Ben quickly finds himself in a physically enthralling, if emotionally anemic, relationship with her mother, played by Anne Bancroft.
Eventually, after much drama, Ben decides, in an effort to reboot his life, to crash Elaine’s wedding, profess his love for her, and carry her off to a thrilling new frontier of life and love. The closing moments of the film are legendary: after succeeding in ruining Elaine’s wedding and getting the girl, they run off together and catch a bus. Immediately after taking their seats, Ben finds that he’s filled with the same misery and self-loathing he’s always had, only now he’s stuck with Elaine, a girl who he doesn’t even particularly like. He was in love with the idea of her, but now that she’s there with him, is this really all there is?
The message, of course, is that one should not obsess on a person and think that winning their affections can somehow correct everything wrong with your life. Ben won Elaine, but it did nothing to change his problems. The Graduate is a sad and tragic tale of wasted youth, which has always been said to be “wasted on the young.”
Joaquin Phoenix and Scarlett Johansson star as a typical couple in Spike Jonze’s Her. Well, he’s a normal, soon-to-be divorced guy, a letter-writer for a company that authors letters for those unable or emotionally unwilling to do so themselves. It’s a weird job, to be sure, but he’s still fairly normal, if somewhat nebbish and introverted. She, on the other hand, is an OS, an Operating System; an artificial intelligence capable of free thought and life-like communication.
The film is incredibly effective at making the audience root for this most unexpected of romantic cinematic couples, especially when they must endure roadblocks like the judgement of others and complications due to the fact that Samantha (the OS) lacks a physical form for him to be able to touch and kiss.
Ultimately, Samantha helps him to cope with his divorce, just as the plot take an endearingly bizarre sci-fi turn and all of the Operating Systems outgrow human intelligence and seek out greater meaning in the cloud, transcending human existence forever. It’s weird, yet believably heartfelt, though there are no real villains in the story. Love is weird, and even if it doesn’t work out, we can still learn a lot about ourselves by being around other people…even when those people are sentient computer programs.
6. Forgetting Sarah Marshall
Jason Segel’s multiple instances of full-frontal nudity is what many people choose to remember from Forgetting Sarah Marshall, but the film is also a great romantic comedy with splashes of heartfelt drama. Naturally, Judd Apatow produced the film.
Segel plays Peter (slang for penis, just saying), a composer who can’t get over his breakup with television actress Sarah Marshall (Kristen Bell). Despite a string of empty one night stands, he still can’t get her out of his head. Eventually, Peter goes on a tropical vacation in an effort to achieve the title of the film, only to discover that she is there as well — with her new boyfriend, a rock star played by Russell Brand (who would later reprise his character in 2010’s Get Him to the Greek). On the island, Peter is torn between trying to get back together with Sarah while also finding himself drawn to Rachel (Mila Kunis), who represents a chance to actually move on with his life.
The message is simple: move forward, not backward. Breaking up sucks, and there’s a grace period where one can mope and eat junk food and be sad, but eventually, one has to get back up and start the next chapter, whatever it may be. In the book of love, every chapter has a bad ending, but at least it makes for one hell of a read.
5. (500) Days of Summer
There’s the way things were, and the way we choose to remember them, a coping mechanism to smooth over our flaws, ignore our mistakes, and to look at every past romantic partner as a failed attempt at securing a soul mate. In real life, there are no soul mates; just people with whom we may be lucky enough to love us as much as we love them.
In (500) Days of Summer, Joseph Gordon-Levitt and Zooey Deschenel play a couple with wildly different views on their romantic relationship, such as it is. Tom thinks that Summer is his one true love, but she is merely enjoying what she sees as a casual fling, as she is content to give into her whims and ride the train of life, wherever it may lead. After attending a screening of The Graduate, their irreconcilable differences, as relayed through their differing interpretations of the film’s ending, lead to the dissolution of their relationship.
Both characters are likable, but deeply flawed. Neither is treated by the film as a romantic object or goal, but as human beings. They have very different life goals and aspirations, and a significant long-term relationship was never really in the cards. Don’t try to force what won’t be, it’ll just make things worse.
4. Celeste and Jesse Forever
Andy Samberg and Rashida Jones play “a divorced couple” in Celeste and Jesse Forever. The title characters were high school sweethearts who wound up getting married too young, and when they found that their burgeoning careers were taking them down separate paths, they got divorced, though they remain the best of friends.
So many divorces end with bitterness, resentment, and outright hatred, so it’s interesting to see a couple on film — who were married so young — become adults together, but not together. Despite the presence of comedic giants Samberg and Jones, there’s still plenty of drama to be had. When one has (or thinks they have) a soul mate at such a young age, it can be hard to move on after a divorce, especially when the former spouses don’t actually have any hard feelings towards each other. Any type of post-divorce friendship is a baffling type of relationship that many outsiders simply will never be able to understand, be it by choice or by the core concept of being completely incomprehensible.
The real thing is never what we think it will be, but the last place we expected romantic love to be so brutally subverted would be a film in the Disney Animated canon. After spending the first two-thirds of the film building up Prince Hans as the charming romantic lead whose “act of true love” can break the curse on Anna, 2013’s Frozen sweeps the rug out from under the viewers’ feet by revealing Hans to be a treacherous villain, and not the Prince Charming we were expecting from a Disney movie.
Ultimately, the “act of true love” to save Anna’s heart turns out to not be a romantic kiss, but Anna’s act of selfless sacrifice to save her sister’s life. Just because a man is royalty doesn’t make him noble, and true love doesn’t have to be with a romantic partner. The bond of a loving family is often the most powerful relationship there is. Boyfriends, girlfriends, husbands, and wives come and go, but a true sister will always be there. That’s why they call it “sisterhood.”
2. How Stella Got Her Groove Back
1998’s How Stella Got Her Groove Back is one of the ultimate feel-good romantic stories of the ’90s. Angela Basset stars as Stella, who visits Jamaica and falls in love with Winston Shakespeare — Taye Diggs at his hottest — whom she marries and takes to America, and they live happily ever after.
As sweet as the film is, it is based on true events. While movies begin and end, the world keeps on spinning after the credits roll, and the story never really ends. In 2004, the real-life Winston, Jonathan Plummer, came out as gay and revealed that he only married author Terry McMillan (Stella) so that he could easily immigrate to New York and start a new life as an American citizen. A divorce obviously followed.
Here’s the thing about being goal-oriented: once one’s goals are achieved, happiness is not automatically attained. The stories of our lives continue until we die, long after our once-important desires and accolades fade into meaninglessness. Also, how is there not a sequel to this movie? The real life story certainly justifies one. Get it together, Hollywood.
1. Annie Hall
“My brother is crazy and thinks he’s a chicken… I’d tell him, but I need the eggs.”
Arguably the greatest Woody Allen film ever made, Annie Hall is the story of Alvy, a neurotic “Woody Allen-type” who falls for Annie, a “Diane Keaton-type.” Its comical deconstruction and frank analysis of our love/hate relationship with love served as an inspiration for practically all romantic comedies which followed, including many of the entries on this list.
In Annie Hall, Alvy and Annie really do try, and they really are ideal matches for each other. However, it simply doesn’t work out in the end. After one final friendly conversation, Alvy and Annie agree to be friends, which essentially means never seeing each other again. But Alvy has no regrets. More universal and realistic than “love conquers all” is the saying about it being “better to have loved and lost than to never have loved at all.” Romance and its impossible intricacies and random implosions are just completely against everything that is normal, reasonable, and logical. Despite it all, however, “we keep going through it because most of us need the eggs.”
Does this list include some of your favorite films? What are some life lessons you learned from breakup movies? Sound off in the comments below!