So to celebrate the holiday, we’ve chosen 10 of the darkest romantic films we could think of. These films aren’t antiromance (The War of the Roses or Who’s Afraid of Virginia Woolf? would have done fine in that instance). In fact, if you look at them under the proper lens, they’re shot through with tender feelings. It’s just that those amorous emotions might manifest themselves in drugs, alcoholism, suicide and the occasional mass murder.
Eternal Sunshine of the Spotless Mind
Michel Gondry and Charlie Kaufman’s mind-bending sci-fi romance reminds us what percentage of relationships are made up of awful, painful moments. After an ugly breakup with girlfriend Kate Winslet, Jim Carrey opts to have his memory erased by a pioneering brain doctor. In the process of stripping away those bitter flashbacks, though, our heartbroken hero realizes that—when it comes to love—even the bad stuff is worth holding on to.
This early film from Peter Jackson (The Lord of the Rings) demurs on whether real-life parent-killing teens Juliet Hulme (Kate Winslet) and Pauline Parker (Melanie Lynskey) actually had a sexual relationship. But their emotional connection is undeniable. Sure, their juvenile romantic bond manifested itself in an overly vivid fantasy world and a bludgeoning death, but those are the sort of trust-building exercises that really bring two people together.
The Honeymoon Killers
There have been countless lovers-on-the-run pictures, but Leonard Kastle’s 1969 cult flick is the ultimate. It’s based on the true story of an obese nurse and a Latin gigolo who met through a lonely hearts club. She’s a sullen, friendless woman. He preys on singletons. But these two broken souls find a connection—one that results in a multistate crime and murder spree. Shot on the cheap in nasty black-and-white, Kastle’s film is a dark and sleazy affair. But it proves that there’s a soul mate out there for even the most homicidal among us.
Leaving Las Vegas
We forget that this bleak, suffocating tragedy about a screenwriter (Nicolas Cage) drinking himself to death in Las Vegas is actually a romance. And a pretty convincing one. Our protagonist falls in with a high-priced prostitute (Elisabeth Shue) who refuses to judge his suicidal lifestyle choice. Sometimes the best thing you can do when you’re spiraling downward is to hold onto someone else and drag them down with you. That, my friends, is true love.
Most people would argue that Vladimir Nabokov’s 1955 novel and Stanley Kubrick’s subsequent 1962 movie are about sexual obsession and manipulation rather than love. But the story’s sad humor comes (initially, anyway) from the fact that poor Prof. Humbert Humbert (James Mason) hasn’t just convinced himself he’s in love with 14-year-old Lolita (Sue Lyon), but that she’s in love with him. Advanced as she may be in the hormonal department, this teenage sexpot’s not capable of truly reciprocating. But damned if Humbert doesn’t make that most tragic of romantic mistakes: thinking he can “change” someone.
Hey, everybody deserves love—even sadomasochistic office workers. This kinky 2002 comedy drama introduces unstable secretary Maggie Gyllenhaal to demanding lawyer James Spader. Pretty soon, they’re turning the employer-employee relationship into a full-contact master-servant situation. Amazingly, the film doesn’t pass judgment, whisking us off to a spankadelic honeymoon by movie’s end.
Sid and Nancy
The Romeo and Juliet of punk rock got their own tragic love story back in 1986, courtesy of cult auteur Alex Cox. Gary Oldman and Chloe Webb fully inhabit the roles of drug-addicted, leather-clad lovers Sid Vicious and Nancy Spungen. The film won’t exactly endear the two to viewers. Sid and Nancy were a couple of annoying junkies. But they were made for each other—from their first meet ... uh, “cute?” to this film’s final taxi cab to heaven.
Here’s another film that people forget is—at its heart—a romance. It’s about a crazy, Vietnam vet taxi driver (Robert De Niro) who meets an attractive campaign worker (Cybill Shepherd). In order to impress her, he takes her to a pornographic movie, shaves his head, buys a bunch of guns, contemplates assassinating a senator and ultimately shoots a pimp’s fingers off. It doesn’t get him any action. But, hey, we’ve all been there.
As I said with The Honeymoon Killers, there have been countless lovers-on-the-run films. This one is pretty much a “best of” compilation of all of them. It’s far better than scriptwriter Quentin Tarantino’s other lovers-on-the-run flick Natural Born Killers (which is lent far too self-conscious a sheen by director Oliver Stone). Here, director Tony Scott takes Tarantino’s words at face value, giving us a gun-loving delinquent (Christian Slater) and a bubbly prostitute (Patricia Arquette) so damn in love they’ll shoot you in the face if you get in their way.
Wristcutters: A Love Story
This blackly funny romantic fantasy from 2006 has yet to achieve its proper cult film dues. Patrick Fugit plays a kid who offs himself after a bad breakup with his girlfriend (Leslie Bibb). Sadly, he finds himself stuck in a depressingly bleak afterlife. Word that his ex has also committed suicide sends him on a cross-purgatory quest to locate her—proving that even death isn’t an impediment to a good romance.