Twisted Romance: The Best Movies About Love Gone Wrong Just in Time For Valentine’s Day

There’s a lot of fucked up romances in cinematic history, and in real life history, for that matter. But honing in on the most twisted is what makes for a truly depraved form of amorousness on V-Day. Below are among the greatest films showcasing loco love at its finest.

Patrick & Evelyn: Not exactly two peas in a pod
Patrick & Evelyn: Not exactly two peas in a pod

American Psycho (2000): Evelyn Williams (whose last name is Richards in the novel) just wants to live a decadent lifestyle with Patrick Bateman, but, in addition to prolonging their engagement and constantly cheating on her with a co-worker’s girlfriend, Patrick has more important appetites to be quenched.

In love with heroin
In love with heroin

Sid and Nancy (1986):It’s a tale as romanticized as that of Romeo and Juliet. The torrid relationship between Sex Pistols lead singer Sid Vicious (Gary Oldman) and angelic (seeming) groupie Nancy Spungen (Chloe Webb) knew no limits–drug-wise anyway. Yes, it’s a classic story of boy meets girl, girls sells boy heroin, boy kills girl.

Promotional poster for The Break-Up
Promotional poster for The Break-Up

The Break-Up (2006): Filmed when Jennifer Aniston and Vince Vaughn were still Hollywood’s “it” couple, The Break-Up is often overlooked as a relic of famous celebrity pairings history–but it’s so much more. While many expected that it would be a quintessential rom-com in terms of its formulaic structure of breaking up and getting back together again, it was not so with the story of Gary (Vaughn) and Brooke (Aniston), who are both too prideful to admit to their faults–going out of their way to hurt one another in order to prove a point.

Linda & Burt: Crazy in love
Linda & Burt: Crazy in love

Crazy Love (2007): Sometimes, the truth really is stranger than fiction. Such is the case with New York attorney Burt Pugach and the object of his desire, Marilyn Riss, in the documentary Crazy Love. Captivated by Marilyn’s beauty, Burt is furious when she denies him, eventually resorting to throwing lye in her face and blinding her permanently. The twist? The two end up getting married.

Dreamin' the days away
Dreamin’ the days away

The Dreamers (2003): Théo (Louis Garrel) and Isabelle (Eva Green) are two siblings living in Paris in the late 60s who prove that you’re always a weirdo when you’re part of a family with non-same sex siblings. After meeting Matthew (Michael Pitt), a fellow cinephile who has come to Paris to study the language, Théo, Isabelle and their parents invite them to stay at their house while the parents are away. Initially pleased, Matthew is disturbed to learn that Théo and Isabelle sleep naked together. This, however, doesn’t stop him from entering into a relationship with Isabelle, which ultimately becomes marred by, of all things, their political stances.

Meet cute
Meet cute

True Romance (1993): Clarence (Christian Slater) and Alabama (Patricia Arquette) are just two lonely souls who happen to encounter one another after Clarence’s boss hires Alabama, a prostitute, to show Clarence a good time on his birthday. When she confesses her profession to Clarence, he’s naturally miffed, but ultimately can’t deny that they’ve fallen madly in love with one another. Their bizarre romance is subsequently made more tainted when a vision of Elvis insists Clarence kill Alabama’s pimp (played beautifully by Gary Oldman, who appears to favor fucked up love stories), prompting a ceaseless hunt for Clarence and Alabama’s whereabouts after Clarence accidentally grabs a bag full of a mob boss’ cocaine, assuming, instead that it belonged to Alabama.

Love among the flowers
Love among the flowers

Harold & Maude (1971): Gerontophilia wouldn’t be where it is today without Harold & Maude. The eponymous characters find themselves in each other’s midst after attending the same funeral (a ritual they both perform as a hobby). Harold (Bud Cort), in his 20s, is refreshed by Maude’s (Ruth Gordon), in her 70s, levity and sense of self-worth. He soon falls in love with her and announces their impending nuptials to his family. Maude, on the other hand, has different plans for celebrating her 80th birthday: death.

Too coy to make a move
Too coy to make a move

Never Let Me Go (2010): What chance can romance possibly have when your entire purpose in life is to donate organs? Apparently plenty when you’re Kathy H (Carey Mulligan). Relegated to a special boarding school called Hailsham, where donor-designed children are trained to be well-behaved and healthy, you wouldn’t think there’d be much in the way of tryst opportunities. Still, Kathy H finds herself falling for Tommy D (Andrew Garfield). Unfortunately, her so-called best friend, Ruth C (Keira Knightley), makes a move first, even though she knows Tommy is truly in love with Kathy. But what’s it all matter anyway when your organs are about to be pillaged?

Making it work on a desert island
Making it work on a desert island

Swept Away (2002): Many will be disinclined to agree that Swept Away should be on a list for anything pertaining to greatness, but my soft spot for Madonna’s film career always gets the better of me. Reinvented from Lina Wertmüller’s original Travolti da un insolito destino nell’azzurro mare d’agosto, Guy Ritchie, who was married to Madonna at the time, gives this incarnation a bittersweet conclusion that is noticeably missing from the more comedic ending of the original. As rich grande dame Amber Leighton (Madonna) struggles to reconcile that she’s got it bad for the hired help, Giuseppe (Adriano Giannini), she finally gives in once they get marooned together on a desert island and he starts smacking her around.

Or so Chloe thought
Or so Chloe thought

Mood Indigo (2013): Love can turn into quite a predicament when it’s tested by a waterlily growing in your girlfriend’s stomach. This, of course, is exactly what happens to affluent gentilhomme Colin (Romain Duris) after he marries the love of his life, Chloe (Audrey Tautou). Spending his fortune to treat Chloe, who must be presented with as many bouquets of fresh flowers as possible on a daily basis, Colin’s love is constantly being put to the financial test. Losing his wealth at an alarming rate, Colin is forced to get a job for the first time in his life, which is obviously a contributing factor to his diminished capacity for love.

Norma's just a little more into it than Joe
Norma’s just a little more into it than Joe

Sunset Boulevard (1950): All Norma Desmond (Gloria Swanson) wanted was love, and she was going to get it wherever she could–in this case, from failed screenwriter Joe Gillis (William Holden). Whether this means a combination of buying his affections and keeping him under lock and key in her mansion, Norma doesn’t care. Unfortunately for her, Joe does.

When it was good
When it was good

Casino (1995): Ginger McKenna (Sharon Stone) proves an equally vile match for Ace Rothstein (Robert DeNiro), the owner of the fictional Tangiers casino in Las Vegas (though it is based on the Stardust), who cajoles her into getting married in spite of her reluctance due to the fact that she’s, well, a prostitute. Ace, nonetheless, promises to provide for her even if things don’t work out–which, naturally, they don’t.

Young, misguided lust
Young, misguided lust

Honorable mentions: Natural Born Killers, Bonnie & Clyde, The Royal Tenenbaums and Badlands.