Essays · Movies

20 Downer Love Stories To Put Your Valentine’s Day In Perspective

Love will tear us apart.
By  · Published on February 13th, 2018

Love isn’t always romance and happiness. Sometimes love hurts, love scars, love wounds, and marks. Maybe that’s because a once-happy relationship has ended and left a gaping hole where your heart used to be. Maybe it’s because the person you chose to spend your life with has passed away, and all you have to look forward to is the day when you can be reunited with them in an afterlife that probably doesn’t exist. Sometimes, though, relationships just lose their spark leaving you feeling trapped in the commitment — like a prison. There’s also the possibility that the person you thought was your steady and trusted companion will cheat on you or leave you for someone else. 

Of course, in some cases you don’t even have to be with another person for love to crush your soul. The worst love can be unrequited and impossible to attain, especially when the one you love only dates jerks who don’t appreciate them like you would. That’s the type of love that made bands like Air Supply and Dashboard Confessional tug at the heartstrings of millions of people worldwide.

There’s a downside to love, and that’s a sad truth most of us have to face at some point in our lives. With Valentine’s Day upon us, Film School Rejects’ romance experts — ‘Randy’ Rob Hunter, ‘Charming’ Chris Coffel, ‘Bootylicious’ Brad Gullickson, ‘Kinky’ Kieran Fisher — have put together a list dedicated to their favorite movies which explore the dark side of love. There’s a variety of titles here, but they all share a common thread of misery.



Casablanca (1942)

Whether you’ve seen the movie or not, you can probably quote all the best lines from Casablanca. “Of all the gin joints, in all the towns, in all the world, she walks into mine.” Humphrey Bogart‘s expatriate has fled the war to find freedom from hard choices as the proprietor of a nightclub. He can deal with the Nazi’s snooping around his door, he can handle the spies desperate to exchange information around his roulette table, but he can’t handle the old flame that takes a stool at his bar. Ingrid Bergman‘s Ilsa is a painful reminder of the man Bogart used to be, and he’s afraid that she’ll rekindle a spark of hope that will get them all killed. Casablanca is a film dripping with melancholy. You want man and woman to get together. You want them to trick the Nazis. You want them to win the war. You’ll have to settle for the return of Bogart’s fighting spirit, and the beginning of a beautiful friendship. – Brad

Psycho (1960)

Marion Crane just wanted to forget the world and run off with the man of her dreams. Her and Sam have been sneaking around in hotel rooms, daydreaming of the moment when they can just be free and open with their affair. Back at the bank where she works, she spots an opportunity to lift a good chunk of cash and ignite her flight of fancy. She flees across the desert, pushing the feelings of guilt deep into her gut. She stops by a cute roadside motel before she collapses behind her wheel, and has a pleasant exchange with the boy manning the check-in desk. Their conversation surrounding the clerk’s ill mother motivates Marion to return the money. Surely there is another way that her and Sam can be together. A quick shower will cleanse her conscience. Enter a psychopathic killer to rob her of those sweet-nothing fantasies. Sam and Marion’s sister will get to the bottom of the atrocities within the Bates Motel, but I’ve always wondered how Sam coped with the loss of Marion after the credits rolled on Alfred Hitchcock‘s demented shocker. – Brad

A Boy and His Dog (1975)

In an apocalyptic wasteland, 18-year-old Vic (Don Johnson) scavenges for scraps to survive with the trusty aid of his mongrel dog, Blood. Technology has connected their two minds, and their telepathic relationship is stronger than any other Vic has had in his life.  The daily life of evading mutants, thieves, and androids gone berserk is starting to grind on Vic’s constitution. He needs a break. A young woman, Quilla June, invades their campfire one day with tales of the “Downunder.” It’s an oasis hidden away from their daily hellscape, and Vic is quick to abandon Blood for both her and its pleasures. The hideaway Eden proves too good to be true, and when their government tries to steal Vic’s sperm to repopulate the Earth, our intrepid hero busts out of the joint with Quilla June in tow. Happily ever after? Up topside, Blood is starving. He needs meat. All Vic has is Quilla June. What’s a boy to do? – Brad

An American Werewolf in London (1981)

Nurse Alex easily falls for the young American man placed under her care. His name is David, and he’s a little off. Apparently, an escaped lunatic has murdered his best friend while they were backpacking across the moors and brutalized his psyche. David claims that the killing was committed by a wolf, and his dreams are plagued with grotesque transformations. The debate around An American Werewolf in London has always been, is it more comedy than horror? I’ve always seen it as a heartbreaking romance between this broken human being and a compassionate nurse suffering a serious case of Florence Nightingale syndrome. The werewolf rampage through Piccadilly Circus climaxes with a heartbreaking confrontation between woman and wolf, and a confession of love that’s answered by a barrage of police gunfire. I chuckle through John Landis‘ film, but I always end in tears. – Brad

When the Wind Blows (1986)

James and Hilda are a retired couple living a simple life in a small home in rural England, and they’re not all that concerned with news reports about Western tensions with the Soviet Union. That changes once war starts and a nuclear missile flattens much of the area leaving them isolated amid the destruction. As days and weeks pass the pair move forward on the strength of their love for each other and an optimism that they’ll soon be rescued. Radiation sickness sets in, vomiting and hair-loss increase, and their hope fades as they slowly die. Oh, did I mention this is an animated film and that the couple is adorably drawn and absolutely heartbreaking? – Rob

Deadbeat At Dawn

Deadbeat at Dawn (1988)

Goose (Jim Van Bebber) is the leader of the Ravens, the biggest and baddest gang in Dayton, Ohio. The Ravens rule the town, but the mean streets of Dayton eventually catch up to everyone. Goose’s girlfriend Christie (Megan Murphy) threatens to leave him if he doesn’t quit the gang, and despite his love for the criminal lifestyle he agrees to call it quits and settle down with Christie. Unfortunately it’s too late for Goose to get out — two goons from a rival gang break into Goose’s apartment, kill Christie, and set him on a path towards revenge. Is Deadbeat at Dawn a love story? Yes, and when Christie dies it’s downright devastating. – Chris

Miracle Mile (1988)

Love at first sight is something of a movie cliche, but when it happens to Harry (Anthony Edwards) after meeting the energetic and light-filled Julie (Mare Winningham) he’s immediately helpless in its grip. They make plans for a first date later that night, but before they can reunite Harry answers a ringing public telephone and hears his world collapse. A nuclear missile is heading towards Los Angeles. Or is it? The film sees Harry’s warning spread through a handful of other late-night city dwellers, and as panic takes hold his desperate search for Julie is finally rewarded as the couple boards a helicopter and flies off towards their new life together… at which point the missile hits, their helicopter crashes into a La Brea Tar Pit, and they sink beneath the tar. – Rob

Leaving Las Vegas (1995)

Nic Cage stars as Ben Sanderson, a Hollywood screenwriter with an alcohol problem so severe it ends up costing him everything. Now unemployed with no family or friends he heads to Las Vegas with one goal in mind — he’s going to drink himself to death. Like most trips to Vegas this one is a bummer from the start, but Ben does end up forming an unusual relationship with a prostitute played by Elisabeth Shue. Unfortunately, their stars aren’t properly aligned and Ben’s addiction ultimately wins out. Grab your beverage of choice, watch this one alone, and wonder why we live in a world that sucks. – Chris

Spawn (1997)

When top government assassin and family man Al Simmons (Michael Jai White) is murdered by his employers because he’s been chosen by the bosses of Hell to lead their army, he’s naturally quite upset. He had it all when he was alive — a wife, a dog, a daughter, a best friend, his natural skin — and losing it broke his heart. But he agrees to lead the forces of the Underworld under the illusion that he’ll see his wife again. However, when he returns to the mortal world — as a crispy demonic hobo — he discovers that years have passed and his baby mother has has married his best friend. That said, his experience is something most of us can all directly relate to. – Kieran

City of Angels (1998)

Seth (Nic Cage) is an angel tasked with guiding humans on their deathbed into the afterlife. He’s fascinated by humans, spending every second watching over them, but he’s unable to truly understand them. He becomes especially enamored with a human by the name of Maggie Rice (Meg Ryan) and decides to become visible to her. As the two begin to hit it off Seth realizes the only way he can be with her is to give up his immortality. As a human Seth begins to experience all the joys of humanity. It’s quite charming to see a naive Cage trying to understand what it is to be human. Because we’re not allowed to have nice things all those good vibes are quickly snatched away when Maggie is struck down by a truck. The movie tries to end on a happy note, but the damage is done and hearts are shattered. – Chris

Irreversible (2002)

On the narrative level this devastating French drama is the simple story of a young couple, Alex (Monica Bellucci) and Marcus (Vincent Cassel), who are torn apart by her violent rape and his tragically misguided effort at revenge. That utter bleakness is magnified, though, by writer/director Gaspar Noe’s decision to play the events out backwards. We open with Marcus involved in a gruesome act of violence, it’s followed by Alex’s assault and the revelation that Marcus targeted the wrong man with his vengeance, and then the film ends with Alex and Marcus overcome with joy having discovered she’s pregnant. They’re happy and looking forward to a lovely future together, but only we know what they don’t. It’s a major punch to the heart. – Rob

The Shape of Things (2003)

There is nothing greater than being in love. You’ll do anything to keep that sensation alive. She doesn’t like you t-shirts, fine, a cardigan is just as comfortable. She doesn’t like you taste in movies, ok, you’ll give her classier arty-farty fair a try. She doesn’t like your friends….hmmm…yeah, maybe there not as cool as you once thought. Paul Rudd‘s nerd will do whatever it takes to keep Rachel Weisz‘s bombshell graduate student in his life. He’ll obey her every command, follow her every instruction, and change his very being to keep that romance going. Before he knows it, the nerd is now a completely different human being. What happens when the love fades? What happens when you learn it was never really there? Who are you now? – Brad

The Clearing (2004)

Wayne (Robert Redford) and Eileen (Helen Mirren) are happily married and nearing retirement. Their idyllic life is shattered one morning when he’s kidnapped by a disgruntled employee (Willem Dafoe), and over the next week Wayne tries to negotiate his way out of danger as Eileen works with the FBI to help find him. Two small wrenches are tossed into the mix, though, with the first being her discovery that Wayne has been having an affair. The second blow to their love hits Eileen and viewers simultaneously — while the film’s editing has led us to believe both halves were playing out at the same time, Wayne’s life actually ended mere hours after his abduction. The hope we shared with Eileen over several days has been in vain as there was never a chance for their reunion. – Rob

Once (2007)

In this heartbreaking tale set in Dublin our would-be lovebirds are simply known as Guy (Glen Hansard) and Girl (Markéta Irglová). He performs with his guitar on the streets while she sells flowers. She’s lured to him by his songs, and the two strike up a conversation about music. After he fixes her broken vacuum the two write some songs and spend a wonderful few days together. That all comes to an end when she says her husband is coming to join her in Dublin. Well, shit. – Chris

(500) Days of Summer (2009)

Back when I was going through the big breakup process some years ago, this movie was my crutch. I was just as pathetic as Joseph Gordon-Levitt’s character, Tom, who spends the movie moping and yearning for the days he recalls being wonderful with the titular Summer. I think this movie captures every stage of post-breakup grief rather well, but it’s also merciful enough to include an outstanding indie rock soundtrack and enough laughs to ensure that us lovelorn souls don’t fall into the abyss completely. – Kieran

Red, White and Blue (2010)

Every time someone comes to me looking for movie recommendations, I always point them in the direction of this revenge-tinged slacker drama from Simon Rumley. And those who have taken my advice on board and watched it have always came back to me with the same response: “Holy expletive, Batman.” Red, White, and Blue is the story of two outcasts — a sexually promiscuous woman and a psychotic war veteran — who befriend each other and find comfort in each other’s company. But when a disturbing revelation leads to some bad things happening to the woman, it triggers the veteran’s more violent tendencies and even more bad things happen. Yikes. – Kieran

Submarine (2010)

Young love is exciting and awkward. For many of us during our teenage years, the world was a scary and confusing place, but having our significant other by our side made us feel ready to conquer it together nonetheless. Of course, that could all change when things start getting too emotional and real — like finding out your lover’s mother has a brain tumour and you acting passive aggressive only to force them into the arms of someone else. I miss those days, but Richard Ayoade’s poignant coming-of-age comedy captures them perfectly. We go through the ups and downs with our teenage protagonists — from their blossoming romance to their emotional breakup and the subsequent despair — and while the ending suggests a reconciliation of sorts, it’s left up to our imaginations to decide if they gave it another go. I like to think they did, but it probably didn’t last. – Kieran

Falling Overnight (2011)

Young Elliot (Parker Croft) stops into a gelato shop one day and meets a photographer named Chloe (Emilia Zoryan). It’s clear from the moment Elliot enters the shop that there is mutual interest, and Chloe extends an invite to an art show for her work happening later that evening. Elliot takes Chloe up on the offer, and the two spend a wonderful evening exploring the city together and getting into all sorts of shenanigans, but as morning approaches Elliot informs Chloe that he’ll be having surgery later that day to remove a brain tumor — and he may not make it. As the movie ends the two lie in bed together contemplating what their future holds. It’s possible that Elliot could be just fine, but any movie that ends with a brain tumor is a total buzzkill in my book. – Chris

Amour (2012)

Michael Haneke tends to make movies which explore the darker side of human nature, but they can still touch us in heartfelt ways, as demonstrated by this masterpiece. Amour is a film about love, life, and death and how they intersect. We follow an elderly couple whose lifetime together has reached its final moments when ill health strikes and their time together comes to a heartbreaking end. We don’t get the happy ending we want to see, but there is some solace to be found in knowing that they spent many special decades together. – Kieran

These Final Hours (2013)

An asteroid has struck the Earth, and humanity is doomed. With an estimated twelve hours before the resulting firestorm hits Australia Zoe tells her boyfriend James that she’s pregnant. Devastated by the news in light of the bigger picture he picks a fight and heads to an “end of the world” party only to realize he’s an idiot. Getting back to Zoe before the conflagration hits, though, becomes a nightmare of its own as he becomes an unintentional protector of a young girl. It’s only on his last day that he realizes the value of both life and love, and then the fire consumes them all. – Rob

Happy Valentine’s Day!

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Kieran is a Contributor to the website you're currently reading. He also loves the movie Varsity Blues.