The 15 Best Enemies-To-Lovers Movies, Ranked

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In real life, the ideal situation is that you meet someone that you, you know, like right off the bat. After all, life is short, and hoping that someone you hate will miraculously turn into someone you love feels like a lot of work when you could just focus your attention on finding a person you get along with in the first place. But that's the real world. In movies, there's something special about the idea of two people who seemingly can't stand one another gradually coming to realize that they can't live without each other. 

Often, their fiery encounters are simply an outlet for the simmering chemistry they can barely contain, making for some of the most memorable on-screen pairings, especially when their feelings for each other begin to deepen. Fairy tale romances are sweet, but where's the fun in watching two nice but bland people fall in love at first sight and go on to live happily after ever? For our part, we have a soft spot for the kind of cinematic romances that start off with a little bit of good old-fashioned emotional toxicity, but reward audiences as their prickly leads melt for one another.

MGM

"Moonstruck" sees Loretta (Cher) all set to marry Johnny (Danny Aiello), a dull but kind man who can offer her a love that may not be passionate, but is comfortable and safe. However, when she meets Johnny's estranged younger brother Ronny (Nicolas Cage), it doesn't take long for her to develop feelings for him — it's just a question of whether they're feelings of love or hate. They have an explosive chemistry, and even when they're fighting, it's never clear if it's going to escalate or if they're simply going to rip each other's clothes off. 

"Moonstruck" adheres to the tenet that a good relationship should have a certain amount of conflict in it to keep things interesting, and the fact that they argue so frequently is indicative of their passion for one another. Audiences clearly connected with the relationship between Loretta and Ronny — "Moonstruck" ended up winning three Academy Awards, including one for best supporting actress, best original screenplay, and best actress.

Universal Pictures

It's not every day that you get to watch Nicole Kidman try to spear Tom Cruise with a pitchfork — unless you're watching "Far and Away," of course. The period drama stars Kidman as Shannon, a wealthy girl who impetuously decides to flee her comfortable home in Ireland for the shores of America, where they're supposedly just giving away land. Tom Cruise, for his part, plays Joseph, a proud Irish farmer who gets himself in a spot of trouble when he tries to kill Shannon's father, his cruel and punishing landlord, but fails spectacularly. 

Although Joseph is perpetually exasperated by Shannon, and Shannon looks down her nose at Joseph, the two escape together, embarking on a journey that will take them across the Atlantic, through Boston, and finally to the Oklahoma Territory. Yes, they eventually fall in love, but before that happens, audiences are treated to scene upon scene of Kidman and Cruise shouting at each other in the most ridiculous Irish accents you've ever heard. What more could you want?

Touchstone Pictures

We've all seen enemies to lovers, but what "Sweet Home Alabama" offers is the rare lovers-to-enemies-to-lovers. Melanie Carmichael (Reese Witherspoon) has successfully shed her Southern roots, launched a notable fashion house in New York, and is about to get married to her politically well-connected boyfriend (Patrick Dempsey), who just so happens to be the mayor of New York City's son. 

But for that to happen, she has to return home to Alabama to tie up some loose ends — namely, the fact that she never officially became divorced from her first husband, Jake (Josh Lucas). However, getting him to sign the divorce papers might be a taller task than she originally thought, largely because, despite their general animosity towards each other, they're still a little bit in love with one another. Come for Witherspoon showing why she's one of the best rom-com actors (with flippy hair that everyone tried to emulate but very few could actually pull off), stay for Lucas' smoldering blue eyes.

Paramount Pictures

What's ironic about "How to Lose a Guy in 10 Days" is that its two leads aren't actually enemies — they just think they are because they're both doing their level best to be the most annoying partner imaginable. Andie (Kate Hudson) is working on a magazine article with foolproof tips to ward off any potential romantic partner, while Ben (Matthew McConaughey) makes a bet that he can make any woman fall for him in just 10 days. You can see where the conflict might come in here. 

Andie's desperately trying to irritate Ben, Ben is trying to woo Andie in a way that probably comes across as psychotic given her behavior, and both of them are furious that their plans are falling apart. But underneath all of that, they're finding moments of chemistry where they emotionally connect with each other in spite of all the disingenuous behavior going around. "How to Lose a Guy in 10 Days" is the rare rom-com that is both genuinely funny and endearingly romantic, in part because of how hard both are working not to fall in love with one another.

Walt Disney Studios

There are a lot of different ways that people can become enemies, but the animosity between a toxic boss and their much-put-upon employee is something truly special to behold. That's what we get in "The Proposal," where Sandra Bullock's Type A book editor Margaret Tate is teamed up with her assistant Andrew Paxton (Ryan Reynolds), who quietly loathes her. Margaret is Canadian, and she risks being deported back to the Great White North — unless, of course, she can convince Andrew to have a green card marriage. 

He agrees (in exchange for a promotion, of course), but the hardest part of their gambit is still to come — convincing the U.S. government that they can stand to be in the same room with each other. When they spend some time together at Andrew's family home in Alaska, however, they start to see something in each other once they're able to get past their shared, contentious history. Bullock and Reynolds are two preternaturally charming rom-com stars, so it's only natural that they would make magic with "The Proposal."

20th Century Studios

A stylish homage to the early 1960s sex comedy, "Down With Love" is all vibrant colors, visual double entendres, and mid-century modern. But at its heart is the relationship between Catcher Block (Ewan McGregor) and Barbara Novak (Renee Zellweger). Catcher is a man about town who delights in his playboy reputation. But he's thrown for a loop when Novak publishes a feminist book called "Down With Love," which argues that women should approach sex the same way that men do, primarily for pleasure and without the expectation of a long-term relationship. 

It's a massive success, and all of a sudden, Catcher finds himself on uneven footing for the first time in his life. So he hatches a plan: He'll get Novak to fall in love with him and write an expose about it, discrediting her take on sexual politics once and for all. To his surprise — but not ours — he's the one who actually falls. McGregor and Zellweger have never been more charming.

Gaumont British Distributors

"The 39 Steps" is not only a great example of enemies-to-lovers in classic Hollywood, but it might just be the first cinematic example of the trope where a couple who hate each other are stuck handcuffed together. Robert Donat plays Richard Hannay, an ordinary guy who ends up embroiled in a spy plot while on vacation in London. After a female spy ends up dead in his apartment, he is forced to go on the run to Scotland and take up her mission to stop intelligence secrets from being smuggled out of the country — all with Pamela (Madeleine Carroll) reluctantly in tow. 

For her part, Pamela spends most of the film not believing Richard's story and actively trying to turn him in to the police, failing to realize the enormity of the situation she's found herself in. Although "The 39 Steps" is a spy thriller rather than a romance, the trajectory of their relationship — as well as the blistering chemistry between the two (especially when they're handcuffed together) — makes it a textbook entry into the enemies-to-lovers subgenre.

20th Century Studios

When accomplished swordsman Don Diego Vega (Tyrone Power) returns home to California from Spain at his father's request, he expects to go into a dull, premature retirement. But when he gets to his sleepy hometown, he discovers his father ousted from his position of authority in the community, supplanted by the dim-witted but power-hungry Luis Quintero. Rather than seek revenge directly, he lies low, pretending to be just a spoiled rich boy with little more on his mind than fashion and complaints about the heat. This is the Diego that Lolita (Linda Darnell) meets, and although he's a good match for her, she's ... well, less than impressed. 

It doesn't help that she's had her head turned by the mysterious vigilante known only as Zorro, who cuts a much more romantic figure than Diego, of whom she's openly contemptuous of. But when she learns that Diego and Zorro are one and the same, and her dull, sleepy suitor is actually an expert fighter determined to save his people from the ruinous leadership of her uncle, let's just say that her opinion of him changes for the better. 

Paramount Pictures

Tristan (Charlie Cox) and Yvaine (Claire Danes) don't exactly meet under the most ideal circumstances in the underrated fantasy romance "Stardust." A fresh-faced, provincial boy who is utterly besotted by his village's resident mean girl, Victoria (Sienna Miller), Tristan proposes to her on a whim, promising to bring back a fallen star as a token of his love. He sets off in search of the star, and realizes to his alarm that it's not just a bit of space dust as he might have imagined, but a living, breathing woman — and one who is none too pleased with the idea of being presented as a prize. (As she says in the film, "Nothing says romance like the gift of a kidnapped, injured woman.")

But Yvaine reluctantly travels with him — she doesn't have much of a choice, mind you, since they're connected by an enchanted rope — and the more time they spend together, the more their shared experiences begin to strengthen their bond. Eventually, their affection grows to love, and when the time comes for Tristan to present Yvaine to Victoria, don't worry, friends — he makes the right choice.

Walt Disney Animation Studios

Come on, these two are so enemies-to-lovers coded that the running joke about "Beauty and the Beast" is that Belle is suffering from Stockholm Syndrome, a reported but widely debunked phenomenon where hostages begin to experience empathy and even love for their captors. Essentially, Belle is her French town's pariah, presumably for the cardinal sin of being a woman who knows how to read. When her father Maurice, the town's cooky old inventor, finds himself trapped in a mysterious castle by a very grouchy beast, Belle courageously takes his place, promising to stay there indefinitely as his hostage. 

All of the enchanted furniture in the castle become convinced that Belle is the only person who can break the spell, turning the Beast and all of his servants into humans again. And to that end, they become a house full of matchmakers, throwing the Beast and Belle together until the two begin to develop affection for one another. Not that we're suggesting that Belle is a bookdigger or anything, but we do clock the about-face in her feelings towards the Beast right around the scene where he presents her with a sprawling, multi-story library. But seriously, who wouldn't fall in love after that?

MGM

Joanna (Goldie Hawn) and Dean (Kurt Russell) don't exactly get off to a good start in "Overboard" — she hires him to build a new closet for her yacht, hates his work, demands that he redo everything in a different type of wood, and then literally throws him overboard. They have such a hostile relationship that when Dean learns that Joanna fell off the yacht later that night and is currently suffering from amnesia, he hatches an extremely problematic plan to claim her as his wife and have her take care of his house and several children until she's worked enough to pay off the outstanding money she owes him for his work on the yacht.

To the astonishment of all, however, after a few growing pains, she fits into their household better than anyone could have imagined, and even improves it. Despite the unsavory origins of their relationship, their burgeoning love for one another feels entirely genuine — largely thanks to the extraordinary chemistry between Hawn and Russell, a couple in real life. Luring a woman into servitude under false pretenses is not what we would consider the start to a healthy relationship, but hey, it works for Dean and Joanna.

Buena Vista Pictures Distribution

A loose adaptation of William Shakespeare's "The Taming of the Shrew" from back in an extremely specific window of time in the late '90s and early 2000s when teen Shakespearean movies were all the rage, "10 Things I Hate About You" blesses us with the incomparable pairing of Kat Stratford (Julia Stiles) and Patrick Verona (Heath Ledger.) But they don't start off as the perfect couple — far from it. Kat is incredibly unimpressed with the boys at her school, which poses a problem for her younger sister Bianca (Larisa Oleynik), who can only date if Kat does (as per her father's rules). A suitor for Bianca's affections, Cameron (Joseph Gordon-Levitt), comes up with a plan: He hires local — and inexplicably Australian — bad boy Patrick to woo Kat, so that he can date Bianca.

In the beginning, Kat regards Patrick with withering contempt. She's suspicious of his overtures, and probably for good reason — after all, he's only dating her because he's getting paid to do so. But before long, the sparks begin to fly, they get to know each other underneath their spiky exteriors, and to quote another Shakespearean play, all's well that ends well.

Columbia Pictures

A lot of times, an enemies-to-lovers story goes from one extreme to another — the characters are fighting, and then they're kissing, and there's not a whole lot of sunlight in between. "When Harry Met Sally" is relatively unique in that the two lead characters (played by Billy Crystal and Meg Ryan) actually spend a great deal of time — years, in fact — as friends. They first meet as college graduates on a road trip from Chicago to New York City, and to say that their personalities clash is an understatement. Sally (Ryan) is uptight and particular, the kind of person who asks for a dozen different modifications to a dish seemingly without realizing how demanding she appears. And Harry, for his part, is morose, cynical, and abrasive. 

But as they meet again and again over the years, in and out of relationships and at different stages in their lives, they begin to develop an unshakeable bond and realize how much they truly care for one another. There's a deep and tender love story lingering beneath the surface of "When Harry Met Sally" — it's not all "I'll have what she's having."

MGM

If there's one thing that's really frustrating, it's when you're perfectly comfortable hating your irritating coworker, only to realize that you're actually in love with them. Such is the case with Alfred (James Stewart) and Klara (Margaret Sullavan) in "The Shop Around the Corner," who work together on the sales floor of a Hungarian shop. Pretty much as soon as they meet, they're getting on each other's nerves. 

But when they begin to correspond anonymously via snail mail, they develop a deep and sincere connection — although neither is aware that the person they're falling in love with is their hated colleague. (If the general narrative sounds a mite familiar, that's because it was remade in the 1990s as "You've Got Mail," starring rom-com superstars Tom Hanks and Meg Ryan.) Directed by Ernst Lubitsch, "The Shop Around the Corner" has become a holiday classic, the acerbic banter between Stewart and Sullavan preventing it from becoming too cloyingly sweet.

Focus Features

This right here, ladies and gentleman, is what we might fairly consider the prototypical enemies-to-lovers story. The 2005 Jane Austen adaptation stars Keira Knightley and Matthew Macfadyen as Elizabeth Bennet and Fitzwilliam Darcy, two stubborn individuals in Regency England who are determined to dislike each other before they've even met. Darcy certainly doesn't make the best of impressions on Elizabeth, after referring to her as "not handsome enough to tempt me," while Elizabeth, for her part, is unwilling to reconsider her negative first impressions of him, even when new information about his character presents itself. 

It's only after a botched (and extremely awkward) marriage proposal and a considerable amount of time together that they both seem to get on the same page — becoming, in the process, one of literature's most enduringly romantic couples. And sorry, but do we even need to mention the hand flex? Jane Austen may have built this ship, but director Joe Wright adds his own iconic flourishes to their simmering relationship, before they even realize they like each other.