I think we can all agree that Hollywood romances are a snore. The same old tired tropes and romantic cliches are recycled over and over again.
When it comes to independent cinema and cult cinema, characters are deeper, more complex… with a buttload more cool factor than their Hollywood counterparts. These films give us something to think about.
Some of the characters on this list are narcissistic, neurotic, weird, sociopaths or even murderous psychopaths but that’s what makes for some quality viewing. These people might be a little bit fucked up… but hey, social outcasts, weirdos and psychos need love too!
Most of these couples are a god damn hot mess but they sure work well on screen, so here goes…
1. Mallory and Mickey Knox – Natural Born Killers (1994)
Oliver Stone’s blood-soaked cult classic follows serial killers Mickey (Woody Harrelson) and Mallory Knox (Juliette Lewis) as they embark on a gory killing spree across the U.S. As the body count increases, they catch the attention of the media who glorify the bloodshed, encouraging the Knox’s to push their excessively violent crimes to the limit.
When it comes to Natural Born Killers, you either love it or you hate it, there are no two ways about it. Personally, I feel like Mickey and Mallory are the captivating and undeniably cool anti-heroes we need. Their traumatic childhoods, their shared fascination with cold-blooded murder and their undying love for one another makes for a great story.
2. Eternal Sunshine of the Spotless Mind (2004)
Shy guy Joel and free-spirited Clementine live in a world where a procedure exists that enables us to erase all memories of past relationships. After feeling spontaneously compelled to visit the same location, on the same day, the pair meet on a train. Little do they know they had already been in a relationship… and it didn’t end well.
Inevitably, they figure out what’s going on and must decide whether to continue the relationship or not. Clementine is adamant that Joel will eventually realise that she’s not the perfect woman he believed her to be and that she’ll eventually become bored of Joel and feel trapped. Even though the ending is left open, we still have to wonder if they’re destined to break each other’s hearts all over again.
3. Lotte and Craig Schwartz – Being John Malkovich (2000)
If you haven’t seen Being John Malkovich, you should because it’s fucking awesome. Without giving too much away, husband and wife Lotte (Cameron Diaz) and Craig Schwartz (John Cusack) discover a portal in Craig’s office that allows them to enter the mind of actor John Malkovich. Weird, right? Well, it gets even weirder. Not only do they start charging others to come in and “be” John Malkovich, while occupying Malkovich’s head, they manipulate him into seducing a woman named Maxine (Katherine Keener). The movie is bizarre but incredibly entertaining.
The question is, whose relationship is more dysfunctional? The couple obsessed with controlling the mind of John Malkovich or the couple where one half is unwillingly being manipulated into a romantic relationship?
4. Seymour and Enid Coleslaw – Ghost World (2001)
Ghost World stars Thora Birch and Scarlette Johansson as BFF’s Enid and Rebecca. The girls are teenage outcasts, graduating from high school and bored by small-town life. While Rebecca has some luck with guys, Enid isn’t so lucky. In fact, she can be kind of a bitch at times.
To ease the boredom of their day-to-day lives, Enid pranks an unsuspecting stranger named Seymour (Steve Buscemi). Seymour posted a missed-connections style ad in a local newspaper’s lonely hearts section. Enid calls him up, pretending to be the woman he was looking for. She arranges a date and then proceeds to watch him being “stood up”.
After a chance encounter at a garage sale, a platonic relationship buds between the two. However, Seymour’s mystery woman contacts him for real. Enid encourages him to go meet her but when the pair start dating, Enid becomes jealous and bitter, which is pretty fucked up since she’s like, 17 and he’s Steve Buscemi.
5. Romeo and Juliet – Romeo + Juliet (1996)
Baz Luhrmann’s critically acclaimed Romeo + Juliet is a modern reimagining of the classic Shakespearean tale. The vibrant sets, costumes and motifs make it a visual masterpiece
While you might think Romeo + Juliet is a straight-up romance movie, it’s more of a gang-crime film. The romantic vibe is maintained through religious iconography, floral shirts and vivid colour pallets.
Just like the original play, there’s some serious beef between two families; the Montagues and the Capulets. In Luhrmann’s version, they’re rival mafia families living in Verona Beach, NY. The ongoing intergenerational hatred continues to affect the younger family members. Nevertheless, Romeo Montague (Leonardo DiCaprio) and Juliet Capulet (Clare Danes) find love despite the resentment and hostility that surrounds them. If you don’t have a little cry at the end, you’re probably dead inside… even though we all know how it goes down for the star-crossed lovers.
6. Marla Singer and The Narrator aka Tyler Durden – Fight Club (1999)
Marla Singer and The Narrator’s relationship was bound to be a disaster from the get-go. They cross paths while gatecrashing support groups for the terminally ill and from there, their unhinged relationship unfolds.
The Narrator is hell bent on fucking up the system, starting with the initiation of “fight clubs” where a bunch of sweaty shirtless men beat the shit out of each other. 🤷 I’m sure you’re familiar with the concept, anyway…
Marla’s no angel either, she’s a cool, trashy, chainsmoking boho chick who has become totally disillusioned with the banality of life. Marla creates her own chaos, be it on a much smaller scale than The Narrator. She steals clothes from laundrettes and sells them to charity shops, overdoses on pills, walks straight into moving traffic. That’s probably why the sociopathic narrator is so attracted to her.
7. Princess Leia and Han Solo – Star Wars (1977)
Han Solo and Leia aren’t dysfunctional as such. However, they did get together after Leia unknowingly almost got it on with her own brother… And their budding relationship just happened to take place during large scale intergalactic turmoil. And they raised Kylo Ren so realistically, something wasn’t right there.
Leia is a sassy, intelligent and incredibly brave princess/senator/general who’s just lost her home planet. Han Solo’s a cool af smuggler who’s motives are kinda questionable at first. Anyway, turns out he’s a nice dude after all.
Leia and Han are both super into each other but are too stubborn to admit it. She doesn’t even mind that his best friend is a big old hairy Wookie. While they’re doing some repairs on the Millenium Falcon, they share a lil’ kiss and it’s cute as hell. There’s always room for some romance, even in the nerdiest of sci-fi movies.
I’m just sad that they got outer-space divorced or whatever because they were good together.
8. Gretchen Ross and Donnie Darko – Donnie Darko (2001)
Ugh, I love this movie. It’s a perplexing psychodrama with elements of science fiction and just the right balance of dark, offbeat humour.
Jake Gylenhall is brilliant as the deeply disturbed but likable Donnie Darko. Donnie’s a highschool student who falls for the new girl in town, Gretchen Ross.
It’s your typical boy meets girl teenage love story, with one minor exception, Donnie is plagued with hallucinations of a sinister rabbit-like creature named Frank who is seemingly warning Donnie that the end is nigh! But that’s ok because while Gretchen might seem like the shy, sweet girl next door type, but she’s got her own issues.
“I guess some people are just born with tragedy in their blood” – Gretchen Ross
Despite Donnie’s attempts to lead a normal life, like going on cinema dates with his new girlfriend, he is pulled into surreal and tragic events with detrimental results.
9. Lux Lisbon and Trip Fontaine – The Virgin Suicides (1999)
Set in 1970s suburban Michigan, The neighbourhood boys are infatuated with the mysterious Lisbon girls. The Lisbon’s are pretty much kept under lock and key by their domineering, super Catholic mother. Especially following the suicide of their youngest sister, Cecilia.
While the boys spend their days dreaming of the Lisbon girls, the Lisbon’s fantasise about traveling the world. They live their lives through pictures in magazines and their imaginations. The imagery that director Sofia Coppola uses paints a picture of a virginal pastel paradise. The film is beautiful, the acting is great and it’s an all-around great movie.
Lux Lisbon (Kirsten Dunst) is the rebellious daughter, sneaking out the window at night to meet boys and smoke cigarettes on the roof. She has the hots for the school heartthrob, Trip Fontaine, going so far as to even write ‘Trip’ on her undies.
Trip’s the kind of dude who’ll finish smoking his joint and strut through the school hallways in a pair of aviators, his well-conditioned hair blowing in the breeze. He’s also the kind of dude who’ll spend weeks pursuing Lux Lisbon and then ditch her as soon as they hook up. When Lux is finally allowed to attend prom, she sneaks off to be with Trip only to wake up on the school football field abandoned. The moment when Lux realises Trip is gonzo, ignited a deep rage in women viewers everywhere.
10. Bob and Charlotte – Lost in Translation (2003)
Another great film from Sofia Coppola, Lost in Translation captures the uncommunicated frustration of unrequited attraction and unspoken desires.
Bill Murray plays Bob Harris, an aging actor who falls for college graduate Charlotte (Scarlette Johansson). The pair meet in a hotel in Tokyo, both quietly suffering as a result of marital problems. Feeling isolated, they find solace in each other and a friendship blossoms. Johansson and Murray each received a BAFTA award for their roles under the categories ‘Best Actress in a Leading Role’ and ‘Best Actor in a Leading Role’.
11. Margot and Richie Tenenbaum – The Royal Tenenbaums
The first post I wrote for this blog was on Margot Tenenbaum. I’m not a huge fan of Gwyneth Paltrow but I loved her in The Royal Tenenbaums. Margot is the adopted daughter of Royal Tenenbaum. She’s a free-spirit and a literary genius. Although she’s had all kinds of romances with all kinds of people, she only has eyes for one man, her adopted brother Richie Tenenbaum.
Of course, he’s technically her brother and she’s married to Raleigh St. Clair (Bill Murray) so that’s a big no, no. When Raleigh suspects Margot is being unfaithful, he hires a private eye who reveals her secret smoking habit, her sexual promiscuity, and her several secret relationships which included a Jamaican recording artist aged 19 and a Parisian woman aged 21. Richie is so upset that he attempts suicide. I think Margot and Richie are definitely one of the more dysfunctional couples on this list but definitely the cutest.
12. Kim and Edward – Edward Scissorhands (1990)
Local Avon lady Pegg Boggs finds Edward alone and abandoned in a creepy gothic mansion near her suburban home. She feels sorry for him and decides to bring him home to her pristine pastel neighbourhood. What she wasn’t expecting was for her daughter, Kim to fall in love with Edward.
Everyone’s a little scared of Edward but they realise that he’s kind and that he can use those freaky scissor hands for amazing haircuts, trimming hedges and styling dogs. Because Kim’s boyfriend is a jealous dickhead, it all turns sour and Edward is chased out of town leaving behind a heartbroken Kim.
I suppose it was probably never going to work because let’s face it, the man has scissors for hands.
13. Vincent Vega and Mia Wallace – Pulp Fiction (1994)
In Tarantino’s classic Pulp Fiction Hitman Vincent Vega is seduced by his big-time criminal boss’ wife, Mia Wallace. I know that Pulp Fiction isn’t a cult film per say but its intriguing characters and unique stylisation have secured somewhat of a cult status over the years.
Mia is cool as a cucumber and Vincent eats it up. She’s a mystery to him and to the audience which might be why she’s such a captivating character despite her relatively short role in the film. While Mia begins seducing him for funsies, it soon becomes apparent that are developing real feelings for one another. They spend the night at a 1950s themed diner, win a twist competition and when they go home Mia accidentally overdoses on heroin, confusing it for cocaine in one of modern cinema’s most iconic moments to date.
14. Veronica Sayer and J.D. – Heathers (1988)
Veronica (Winona Ryder) is friends with three rich bitches all named Heather, each one as stuck up as the next. After a falling out, Heather Chandler vows to ruin Veronica’s life. Simultaneously, the new kid in the school, rebellious cool dude J.D. (no last name, because he’s that cool) catches Veronica’s eye. J.D. murders Heather Chandler by making her drink drain cleaner. That first act of murder kicks off a gruesome killing spree.
J.D. and Veronica are a hot couple who just so happen to get off on murdering people. I won’t say too much but as you might have guessed, it does not end well for Veronica and vicious psychopath J.D.
15. Chiron and Kevin – Moonlight (2016)
Moonlight is coming of age drama set in Miami, Florida. It’s about two black kids, Kevin and Chiron, who fall in love. Kevin and Chiron are from a pretty shitty area in Miami. Chiron’s mother is an addict and life isn’t easy for either of them. The film follows Chiron throughout his life, from childhood to adolescence to adulthood.
After Chiron attacks a bully in school and is arrested, the boys part ways indefinitely and their lives take very different turns. Moonlight addresses issues like addiction, sexual identity and the ways in which the system so often fails people of colour.
This movie inspired my thesis on queer cinema. I think Moonlight is one of the greatest movies I’ve ever seen and my god did it break my heart.
16. Lula and Sailor – Wild at Heart (1990)
David Lynch’s classic Wild at Heart tells the lovers on the lam tale of Lula and Sailor. Head over heels in love, the pair are separated after Sailor kills a man who attacked him with a knife. It turns out, *dun dun dun* Lula’s lunatic mother took out a hit on Sailor.
When Lula picks Sailor up from prison, they decide to break his parole and run away to California. Lula’s mother hires a bunch of gangsters to track the couple with the intention of murdering Sailor.
Wilde at Heart is a weird, twisted and funny take on a road movie. It wouldn’t be a David Lynch movie if there weren’t some particularly bizarre scenes thrown into the mix.
And who doesn’t have a soft spot for Nick Cage?
17. Annette and Sebastian – Cruel Intentions (1999)
Ok, so first things first, Sebastian is trying to seduce Annette Hargrove because if he does, his step-sister Kathyrn (Sarah Michelle Gellar) has promised to sleep with him as part of a wager between the two. Their relationship is off to a great start.
So, anyway, Annette has recently published a book about saving herself for marriage, much to the amusement of the overtly promiscuous step-siblings.
What Sebastian doesn’t expect is to genuinely fall for Annette. Annette is familiar with his reputation as a womaniser, so even when she develops feelings for him, she refuses to pursue it. Without giving the whole plot away, lots more shady shit goes down which leads to Kathryn trying to sabotage the whole thing like the stone cold bitch she is.
18. Lars and Bianca – Lars and the Real Girl (2007)
Ryan Gosling plays Lars Lindstrom, a man with emotional problems that prevent him from truly living his life. After many years spent alone, Lars introduces his new girlfriend, Bianca. The only thing is, Bianca just happens to be a doll he ordered online. (awks)
Everyone is understandably weirded out by the whole thing. They do however understand that Bianca is helping Lars to interact more with people, leading them to come around to the idea. Initially, the plot comes off as kind of perverted but it’s anything but that. Lars and the Real Girl is a sweet, heart-warming comedy and in my opinion, it’s Ryan Gosling’s best performance (rivaled only by Drive, 2011).
19. Sophie and Ethan – The One I love (2014)
I randomly picked this movie on Netflix when I was hungover and I was pleasantly surprised. In this sci-fi/thriller, Elisabeth Moss (The Handmaid’s Tale, Madmen) and Mark Duplass (Creep, The League) star as a couple who are going through a bit of a rough patch. Their therapist sends them on a weekend retreat to a secluded cottage in the country. With their marriage on the rocks, they agree to go.
They smoke a joint to relax, and afterward, Sophie goes to the guesthouse where her and Ethan sleep together, only to come back and find Ethan asleep on the couch in the cottage. Ethan has no recollection of being with Sophie. Some other very fishy stuff happens, it’s not long before the couple is caught up in some crazy doppelganger shit with lots of twists and turns.
20. Zia and Mikal – Wristcutters: A Love Story (2006)
Wristcutters: A Love Story is a dark comedy/road movie about a man named Zia who commits suicide and ends up in some sort of bleak limbo. Zia goes on a road trip with his new found friend Eugine. He is trying to find his ex-girlfriend who has also killed herself.
Along the way, they pick up a hitchhiker, a woman named Mikal. Mikal is played by Shannyn Sossamon who you might remember from The Rules of Attraction (2002) or Kiss Kiss, Bang Bang (2005). Mikal is looking or the P.I.C or People in Charge because she believes that she was mistakenly sent there. Of course, Mikal and Zia start falling for each other which creates tension seeing as Mikal is trying to be sent home by the P.I.C
And there you have it, 25 iconic fucked up movie romances. I hope you enjoyed this article and that it might encourage you to watch some of these amazing films. Thanks for reading. ✌
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