From low-key stalking in popular love songs to full-on abuse in classic literary romances, it can be hard to understand why an old song or movie ever made us swoon. But as this list shows, we’re far from dealing with our creepy ideas about what counts as love. These movies, songs, and books may claim to be about romance, but if we look a little closer, we just might see a heck of a lot of warning signs. Beware Cupid! Here are some of pop culture’s diciest “love stories.”
Bad Pop Culture Romances Facts
1. Titanic
Love is patient, love is kind, love means moving over so that Leo DiCaprio won’t get left behind. This movie’s ending ticked off thousands of viewers—and for good reason! When Myth Busters put Titanic’s conclusion to the test, they proved that if Rose had made some room, Jack would have survived. Everyone always talks about how James Cameron is this visionary director committed to the latest technology. If that’s the case, how is he stumped by a floating door?
2. “I Will Always Love You”
Most people associate this song with Whitney Houston and Kevin Costner’s tender romance in The Bodyguard. But fun fact: Not only was this song actually written by Dolly Parton, it's not about romance at all. It's an ode to her jealous boss Porter Wagoner, who launched Parton's career and then became controlling and bitter when her star ascended and his fell. The song's original meaning was, loosely translated, “Goodbye forever, you egotistical tool.”
3. “Father Figure”
This song takes “daddy issues” to a whole new level. George Michael sings about wanting to be “bold and naked at your side” but the comparison he uses to describe his love is...being his boyfriend’s dad? No lie: He “will be your father figure, put your tiny hand in mine.” As though that “tiny hand” detail wasn’t creepy enough, Michael also wants to be greeted with the “eyes of a child.” No, thank you. Decline. Unsubscribe.
4. Pretty Woman
Pretty Woman is a top tier rom-com, but the original script went in a much darker direction than the sweet movie that audiences know and love. Instead of sending call girl Vivian and businessman Edward off into the sunset, the movie would have ended with Vivian on a bus staring “emptily” into her dark future. Yikes.
Pretty Woman, Paramount Pictures
5. Twilight
After plenty of thinkpieces, most of the internet understands that the Twilight book series glamorizes highly dysfunctional relationships. Edward is literally decades older than his girlfriend, who he isolates and controls. He’s madly possessive and jealous, watches her sleep, constantly says that he might kill her, and threatens to end his own life if she leaves him.
6. New Moon
But by far the most entertaining takedown of Edward Cullen comes from Cullen himself. Robert Pattinson’s trollery of the Twilight franchise is legendary for a reason. He’s said that his character is basically “an ax murderer,” the series’ author Stephanie Meyer is “mad,” there is “something wrong” with Bella and Edward, and that their relationship is “traumatic.”
7. I Love Lucy
On TV, it looked like Lucille Ball and Desi Arnaz were the picture of happiness, but in real life? Not so much. Just one day after I Love Lucy wrapped up production, Ball filed for divorce from her “nightmare” marriage to Arnaz, who had a history of womanizing and alcohol abuse. After years of playing a happy couple, their split was one of the most high-profile breakups in Hollywood history.
8. “One Way or Another”
This Blondie song sounds like a standard romantic pursuit until you learn about its creepy backstory. Debbie Harry wrote the track based on her experiences with a possessive ex-boyfriend. Once their relationship soured and she left him, he started stalking the singer. “One way or another, I’m gonna find ya, I’m gonna get ya get ya get ya get ya” just got a lot less catchy.
9. “Age Ain’t Nothing But A Number”
Aaliyah was beautiful, talented, and taken from us far too soon, but the first thing that pops into most people’s heads when they hear this song has nothing to do with her artistic achievements. Instead, this R&B number is a queasy reminder that Aaliyah and R. Kelly got illegally married when Aaliyah was just 15 years old and R. Kelly was nearly a decade older at 24. Aaliyah’s parents annulled the marriage when they realized what had happened.
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10. Wuthering Heights
Ever since Emily Brontë’s Byronic hero burst onto the scene in 1847, controversy has followed in his wake. Is Heathcliff a romantic, misunderstood victim, or a brutal monster? Sure, this anti-hero hangs a dog, marries a girl just to make his ex jealous, and ruins everyone’s lives, but when Hollywood keeps casting hotties like Laurence Olivier and Tom Hardy as Heathcliff, it’s easy to see why women get mixed messages about whether or not they should like this guy. For the record, I vote no.
11. “Love the Way You Lie”
This Eminem and Rihanna song is genuinely disturbing. With lyrics like “If she ever tries to leave again, I’ma tie her to the bed and set this house on fire,” Eminem raps about a dysfunctional relationship while Rihanna sings the chorus about liking “the way it hurts.” To make matters worse, this song came out shortly after Rihanna’s domestic violence case against Chris Brown made news, making listeners wonder if a sleazy record executive decided to exploit her experiences into a controversial top 40 hit. On another note, the music video pairs Megan Fox with one of the hobbits from Lord of the Rings so...that happened.
Wikimedia Commons, Brandy Shaul
12. Bear
The controversial Canadian novel Bear by Marian Engel is about a dowdy woman named Lou who’s tasked with cataloging a library in northern Ontario. As she flicks through books and documents, Lou also finds time to come into her own sexuality by, um, getting it on with a bear. Literary critics defend the book as an allegory about second-wave feminism, but the public still finds it tough to get past the whole bear thing. Same.
13. Breakfast at Tiffany’s
Audrey Hepburn fans adore her iconic role as Holly Golightly, but not everyone was as enthusiastic. Truman Capote wrote the book that inspired the movie and he, for one, was appalled by the film. Even though the movie gives Holly a happy ending with her neighbor George, Capote’s book had a much darker ending. Holly is a sex worker who survives by romancing wealthy men. George has his own sugar mama and by the end of the book, they just have to keep on keeping on. There’s no romantic rain-soaked reunion in sight.
14. Love
This Old Hollywood adaptation of Anna Karenina featured one of cinema’s most famous real-life couples: Greta Garbo and John Gilbert. Heck, the movie’s tagline even punned on their relationship by billing the flick as “Garbo and Gilbert in Love.” But in real life, the stars did not enjoy wedded bliss. After Gilbert proposed seven times, Garbo finally said yes...only to leave him at the altar.
15. “Crazy”
On its own, this Aerosmith song is a standard ballad about a girl driving a man “crazy.” What makes this song so strange is the video, where Liv Tyler and Alicia Silverstone play the crazy-making women in question. It sounds fine...until you remember that Liv Tyler is Steven Tyler’s daughter. As he wails “I know you ain’t wearin’ nothin’ underneath that overcoat” over footage of his own daughter, well, it’s pretty awkward.
Wikimedia Commons, Julio Aprea
16. Casablanca
This classic Hollywood movie has gone down in history as one of the most swoon-worthy flicks of all time—but behind the scenes, those “romantic” scenes didn’t come naturally. Because Humphrey Bogart was shorter than Ingrid Bergman, all the scenes where they kiss were filmed with him standing on a box so that he’d look taller. Suddenly those embraces are a lot less swoon-worthy.
17. Manhattan
On its own, Manhattan’s pairing of middle-aged Isaac and teenaged Tracy is already controversial, but it gets worse thanks to the actor-director Woody Allen’s social life. Allen infamously married his ex-partner’s adopted daughter Soon-Yi Previn. Between the paternalism and the 35-year age difference between Allen and Previn, the older-man-younger-woman romance in Manhattan carries a lot of baggage.
18. Some Like It Hot
Marilyn Monroe and Tony Curtis had one of Old Hollywood’s most torrid on-off romances. Does that mean it was a good idea to make a film together? Probably not. By the time Some Like It Hot started shooting, Curtis was falling out of love with Monroe. He even described kissing her as “like kissing Hitler.” Ouch.
19. Gone with the Wind
Margaret Mitchell’s book and the classic Clark Gable/Vivien Leigh Hollywood movie share one overarching theme. A landmark civil rights movement can—and should!—be relegated to the background so that a plantation owner and a Confederate soldier can fall in love. This love story...guys, it did not age well.
20. Begone with the Racist Hotel
Hattie McDaniel made history for being the first Black woman to win an Oscar for her role as the housekeeper in Gone With The Wind, but she was treated horrifically on what should have been the best night of her life. The hotel that hosted that Oscars refused to let Black people stay in its rooms and only deigned to allow McDaniel in when a studio executive called in a favor.
21. “He Hit Me (And It Felt Like A Kiss)”
Despite its boppy tune, this song by the Crystals is about a terrifying relationship. In case the song’s title didn’t give it away, the 1962 ditty describes how “He hit me and I knew he loved me.” The abused woman justifies her man’s actions by saying “If he didn’t care for me, I could have never made him mad. But he hit me and I was glad.” Wow.
22. Flowers in the Attic
There is no surprise revelation in this entry, just a completely baffling episode in the history of Young Adult books. Back in 1979, V.C. Andrews wrote an incredibly controversial novel about a young girl named Cathy who is going to need a lot of therapy after the book’s final pages. Long story short: Cathy’s father dies, leading Cathy, her siblings, and their mom to live with Cathy’s evil grandmother. When the grandma locks the kids in the attic, Cathy starts a romantic relationship with her only option: her own brother Chris. As though that’s not enough, the book doesn’t clearly criticize the relationship, which is why we have numerous sequels, film and TV adaptations, and lovelorn fan videos about the incestuous couple.
Flowers in the Attic (2014), Lifetime
23. Friends
In the years since Friends went off the air, we’ve all missed the beloved sitcom...well, except for one thing: Ross’ character. For many cultural critics, Ross’ creepy ways have not aged well. From dating one of his students to manipulating Rachel, in retrospect, the internet has experienced an intense backlash against Ross. Maybe Rachel should have ended up with Joey.
24. Romeo and Juliet
Hot take: Shakespeare’s play is less about star-crossed lovers and more about raging adolescent hormones. With all the fanfare and endless adaptations, it can be hard to forget that Juliet is just 13 years old and that the kiddos only know each other for three days before they die for love. As if that wasn’t enough, feminist critics also interpret the play as an indictment of the Capulet and Montague patriarchs. After all, if the dads just quashed their beef, both of their kids would still be alive. Just saying!
25. 50 Shades Of Grey
A major study of this book showed that “almost every interaction” between Christian Grey and Anastasia Steele involves some kind of emotional abuse. From threatening Anastasia to refusing to accept that “No means no,” Christian is a guy with a metric ton of issues. It’s no wonder multiple groups called for a boycott of the movie.
26. Big
When you think of the movie Big, you probably think of the charming scene where Tom Hanks plays that huge piano in a Manhattan toy store. You probably don’t immediately recall the sinister sub-plot where Elizabeth Perkins’ career woman Susan goes to bed with a 12-year-old boy stuck in a full-grown man’s body. And yet, it happened! Even worse, the movie ends with Susan realizing what she’s done and numbly waving to her adolescent lover.
27. “Je T’aime...Moi Non Plus”
Few people realize that Serge Gainsbourg originally recorded this erotic song with his girlfriend Brigitte Bardot. When Gainsbourg wanted to release the tune, there was just one problem: Bardot was married and had been cheating on her husband with Gainsbourg. She knew her husband would be furious if the steamy duet got out. Gainsbourg agreed to keep the song a secret...before re-recording it with his new girlfriend, Jane Birkin. Ouch.
28. “Do What U Want”
Lady Gaga’s suggestive collaboration with R. Kelly was a hit back in 2013, but since then, she’s gone on to remove it from re-releases of her albums and request that streaming services take down the song as well. It’s easy to see why. The provocative song explicitly encourages R. Kelly to do whatever he likes to Gaga’s body, which is a startling request given the accusations of assault that have followed him for decades.
29. Pop Ditty or Cry for Help?
Unfortunately, the story behind this single gets even worse. When fans pointed out that Lady Gaga was wrong to collaborate with Kelly, she explained that the “twisted” song was written at “a dark time in [her] life” when she still hadn’t “processed the trauma that had occurred in [her] own life.” Lady Gaga had recently revealed that when she was a teenager, she was a victim of assault.
30. While You Were Sleeping
There are a lot of creepy men on this list, so let’s take a moment to balance things out and remember Sandra Bullock’s sketchy transit worker in While You Were Sleeping. Bullock is incredibly charming as Lucy, but the sinister plot makes it hard to find her anything but creepy. In one of Hollywood’s more convoluted meet-cutes, Lucy has a crush on Peter, a customer who almost gets run over by a train. Luckily, Lucy saves him from getting hit, though he ends up in a coma. When his family comes to visit, they get the wrong idea and assume that Lucy is Peter’s fiancée. She lets them think this for an uncomfortably long time, low-key manipulating a nice family whose son nearly died.
While You Were Sleeping, Buena Vista Pictures Distribution, Inc.
31. Flip it and Reverse it
Evidently, studio executives knew the plot of While You Were Sleeping could easily become uncomfortably “predatory.” Originally, the movie was supposed to feature a woman in a coma and a male Lucy, but after thinking about that premise some more, they decided that it was just too dicey. In the end, the studio switched the genders and cast an absurdly likeable actress to sell a stalker’s fantasy as a love story.
32. The Great Gatsby
Did you know that The Great Gatsby was based on a true story? Yup, the basis of Gatsby is the famous rags to riches bootlegger George Remus. Remus married a woman named Imogene Holmes, only to be left high and dry when Imogene took George’s money and ran. But don’t worry: George got his revenge. He demanded that his driver run Imogene off the road, then George shot his back-stabbing wife. As you probably figured out, Imogene stood in for a mixture of Daisy and Myrtle.
The Great Gatsby (1974), Paramount Pictures
33. Where’s Miss Marple When You Need Her?
Jack drifting off to eternal sleep isn't the only unromantic thing about Titanic. While the cast and crew of Titanic were busy wrapping up the scenes set in the present day, they broke for lunch and had some chowder. But then, everyone started to feel strange. Soon enough, they realized that the chowder was not normal. Someone had spiked it with PCP, leading people to go on horrific trips and have terrifying flashbacks. To this day, no one knows who was the culprit.
34. “Every Breath You Take”
Ah, the stalker’s anthem. Full of lyrics like “Every move you make, Every bond you break, every step you take, I'll be watching you,” it's hard not to get creeped out by this ditty. While Sting claimed the track was an “I’m here for you” note to his ex-wife Frances Tomelty, Occam’s Razor taught us that the simplest solution is usually right. As such, it makes sense that many critics find this song just plain creepy. It’s only a matter of time before Netflix uses it in the trailer for the next season of You.
35. Never Been Kissed
Drew Barrymore is absolutely charming in this movie about a reporter who goes undercover at a high school, but the romantic subplot is kind of dicey. As Barrymore’s character Josie integrates into her school’s community, she forms a bond with one of the few people who’s actually her age: Her English teacher, Mr. Coulson. To his credit, Coulson is creeped out by his attraction to Josie and they only get together when the jig is up, but there are quite a few “romantic” moments that toe the line.
Never Been Kissed, 20th Century Studios
36. “Baby It’s Cold Outside”
This duet takes place on a should-be romantic snowy evening. As the winter sets in, a woman realizes that it’s time for her to head home—only for her male companion to insistently suggest that she stick around. Of many choice lyrics, “Hey, what’s in this drink?” is the most sinister. While plenty of people defend the song, some radio stations have taken it off the air.
37. Knocked Up
This 2007 romcom saw Katherine Heigl play Alison, an over-achieving, high-strung woman who accidentally gets pregnant with Ben, played by Seth Rogen as a fun-loving slacker. Even though it made bank at the box office, this movie is best remembered for the controversial comments of one of its stars. Heigl said that she thought the flick was “a little sexist. It paints the women as shrews, as humorless and uptight, and it paints the men as lovable, goofy, fun-loving guys.”
38. Fired Up
At the time, Heigl’s comments caused a huge upset but looking back, she was right! Instead of painting Alison as a killjoy, this movie might explore the fact that she has to work extra-hard because women are still paid 78 cents for every dollar a man makes. Or maybe Alison only looks like a shrew to Ben because he gets to enjoy living in a society that doesn’t judge him for being lazy. Just saying.
39. Lolita
Most people recognize that Vladimir Nabakov’s novel is not a romance, but a deep dive into a pedophile’s psyche. Narrated by Humbert Humbert, Nabakov’s book explores the ways that a predator justifies his own actions. The book’s sick genius lies in the way that Nabakov’s prose temporarily beautifies Humbert’s relationship with Lolita—though as we keep reading, any potential enchantment evaporates. As Lolita matures, Humbert’s “love” is revealed to be selfish, abusive, and profoundly manipulative.
40. Sabrina
Sabrina is one of Hollywood’s classic Cinderella stories. Starring Audrey Hepburn as the titular chauffeur’s daughter, the movie watches as a meek young woman blossoms into a sophisticated lady and gets to pick between David and Linus, the loaded Larrabee brothers. But behind the scenes, this flick did not have a happy ending.
41. The Opposite of All’s Well That Ends Well
Co-stars Audrey Hepburn and William Holden fell madly in love while shooting the movie and even meant to get married—until Hepburn learned that Holden couldn’t have children. Both actors left the set of this “romantic” flick broken-hearted.
42. Jane Eyre
Classic romance right here. Boy meets girl, boy falls in love with girl, boy and girl almost get married, only for the ceremony to be interrupted because it turns out that boy locked his real wife in an attic. Oh, and then girl almost marries her own cousin but comes back to boy after his ex-wife lights the house on fire and dies. Swoon.
43. The Mad Woman in the Attic
In the years since Jane Eyre was released, literary critics have had a field day with Charlotte Brontë’ s wacky romance. For some, the novel is a protest against the patriarchy. For others, it’s a critique of colonialism. Rochester’s Creole first wife isn’t a monster, but a victim whose fate represents the terrible suffering of so many women of color in the nineteenth century. Either way you slice it, Jane Eyre is not your cookie-cutter romance.
44. The Breakfast Club
Looking back, it’s hard to understand why some jokes were ever funny. Unfortunately, that’s the feeling that Molly Ringwald gets when she watches beloved 1980s movies like The Breakfast Club and Sixteen Candles. In an essay, Ringwald wrote about how in The Breakfast Club, Ringwald’s love interest insults her, sneaks a peek at her underpants, and, though it’s suggested rather than shown, touches Claire without her consent. Looking back, the actress has mixed feelings about the hit movie. But in Sixteen Candles, things get so much worse.
The Breakfast Club, Universal Pictures
45. Sixteen Candles
While most people remember Sixteen Candles as a light-hearted romp through one wild high school night, a chilling subplot casts a pall over the tender romance between Ringwald’s shy Samantha and the heartthrob Jake Ryan. The trouble with Sixteen Candles goes back to one minor character: Jake’s girlfriend Caroline. Caroline isn’t a very sympathetic character. Bossy and shrill, she’s the princess blocking Samantha and Jake from getting together. Because Caroline is unlikable, audiences didn’t have a problem with her horrific fate: multiple men pass her drunken body around and do what they want with her, and it’s all played for laughs.
Sixteen Candles, Universal Pictures
46. Burn It Down
In Sixteen Candles, no one cares that Caroline can’t consent to their advances because Caroline’s not a person—she’s just an object. During a scene that makes Jake Ryan very hard to like, he hands Caroline off to the Geek, played by Anthony Michael Hall, and says, “Have fun.” The Geek does. He goes all the way with Caroline, who remembers nothing about their tryst the next morning. In the 1980s, that read as a triumph for the Geek. In 2020, it’s assault.
Sixteen Candles, Universal Pictures
47. “Drunk In Love”
Beyonce’s song “Drunk In Love” features a curious line where her husband Jay-Z raps “‘Now eat the cake, Anna Mae,’ said ‘Eat the cake, Anna Mae.’” Well, it turns out that line is pretty darn dark. Jay-Z is referencing a scene from a Tina Turner biopic where her abusive husband Ike orders her around before assaulting her. What is this lyric doing in a song about love?
48. Shakespeare’s The Winter’s Tale
Let’s set the scene. It’s Ancient Sicily and everything’s going great for the royal family. Or it is until King Leontes throws his life into a blender. Leontes starts thinking that his virtuous wife Hermione is seeing another man on the sly. He publicly accuses her of cheating on him. For some reason, she decides that she’ll win back this trash man by faking her own death—but she doesn’t stop there. She then lives as a recluse for 16 years, pretends to be a statue, and “comes back to life” to reward Leontes’ change of heart. Is Shakespeare trolling us with this wackadoodle “romance” or is he for real? I’m in too deep and have no idea anymore.
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