You probably didn’t go to the movies much the year you were born, but checking out the films from your birth year can give you a window into the cultural milieu that was your introduction to the world. Take special note of the love stories. If you were born later in the year, inspiring chemistry on the big screen may have played a small part in your very existence. Here are the most romantic movies from 1950 to 2000.
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Thirteen years after Snow White sang, “Some Day My Prince Will Come,” Walt Disney found true love again with “Cinderella.” The 2,000-year-old story saved Disney from bankruptcy and set the studio on a magical track to success. More than seven decades later, Cinderella Castle still welcomes visitors to Disney World in Florida and graces the company’s logo.
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French ballet dancer Leslie Caron made her acting debut, opposite Gene Kelly, in this Best Picture winner. “A delightfully entertaining show from beginning to end,” gushed the Baltimore Sun. The bold, colorful musical culminates in an epic 17-minute dance number, which includes a sensual duet that was considered so provocative that it was cut out of the film in some countries.
Gene Kelly followed up “An American Paris” with another romantic masterpiece, although at the time it wasn’t as well-received. The glorious feeling of being in love is brilliantly captured in this musical, co-starring Debbie Reynolds. Despite Kelly singing and dancing in the rain alone, the movie’s most famous scene was hotter than it seemed. While filming it, the actor was sick with a high fever.
Newcomer Audrey Hepburn instantly became Hollywood royalty after playing Princess Ann in “Roman Holiday.” In retrospect, it seems like no surprise that fans effortlessly fell in love with her (and the Vespa scooter she briefly zipped around on with Gregory Peck in the film). “An American Paris,” was filmed almost entirely on sound stages in Hollywood, but the Rome in “Roman Holiday” was the real Rome. If it hadn’t been, the film might have been less authentic but more colorful. The movie was made in black and white for budgetary reasons.
Audrey Hepburn struck romantic gold again with this Cinderella story, about a chauffeur’s daughter who’s in love with one wealthy brothe while being pursued (under false pretenses) by the other. “The upper-crust comic romance often gets just the measures of erotic delight and bubbly champagne fizz it needs,” reads a Chicago Tribune review. Some critics prefer the 1995 remake.
“Whatever it is that women like, I ain’t got it,” laments the title character in this Oscar winner. Audiences flocked to watch a hopeless Bronx butcher (Ernest Borgning) fall for an unlucky-in-love teacher (Betsy Blair) in this critically acclaimed drama. It’s your basic basic-boy-meets-basic-girl plot, but that’s the appeal. The film’s writer dubbed it “the most ordinary love story in the world.”
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Upon the film’s release, The New York Times warned, “If you don’t go to see it, believe us, you will be missing a grand and moving thing.” While the Rodgers and Hammerstein musical only flirts with the idea of connecting characters from two different worlds, songs like “Hello, Young Lovers,” “Getting to Know You,” “Shall We Dance,” and “Something Wonderful” help qualify the movie as a romantic classic.
What happens on an ocean liner stays on the ocean liner. That is, unless you’re Deborah Kerr and Cary Grant in “An Affair to Remember.” After a secret romance at sea, their characters make plans to meet up again six months later at the top of the Empire State Building. But will it happen? Fans of soap-operatic dramas are destined to have all the feels as the plot plays out. If you find yourself remembering “An Affair to Remember” while watching the 1994 film “Love Affair,” that’s because it’s based on the same screenplay, originally written for a 1939 film. Anybody remember that one?
While not romantic in a traditional way, this Alfred Hitchcock masterpiece gives viewers much to ponder about the devastating consequences of romantic obsession spun out of control. Considered by some to be the greatest movie of all of time, the film was not love at first sight for moviegoers. It garnered just $1.5 million in box-office returns, spare change compared to the top-grossing film of the year, “South Pacific,” which brought in nearly $37 million. Apparently, film fans of the day were in the mood for an enchanting evening of a different sort.
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In the late 1950s, shared telephone party lines were still a thing, much to the chagrin of Doris Day’s character, Jan Morrow, in this classic rom-com with an Oscar-winning screenplay. Jan is aggravated at having to share a phone line with Rock Hudson’s character, Brad Allen, whom she finds rude and distasteful. Of course, she has a chance to reassess her opinion as the plot progresses. The film was the first time the two actors were paired together, but the positive talk about “Pillow Talk” resulted in two more Day-Hudson love stories, “Lover Come Back” and “Send Me No Flowers.”
The abrupt shift in cinematic sexual mores of 1960 worked out well for the lead character in “The Apartment,” C.C. Baxter (Jack Lemmon) and the woman he’s interested in, Fran Kubelick (Shirley MacLaine). Oscar had no trouble rolling with the times. The movie won five Academy Awards, including Best Picture.
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Somehow, some day, somewhere, it was inevitable that the hit 1957 Broadway show would be turned into a spectacular film. “West Side Story” picked up 10 Academy Awards, including Best Picture. Tony and Maria are set to sing and dance the story out again soon. Steven Spielberg offered up a new “West Side Story” in 2021.
“I suppose I’m not the first person to discover, a girl doesn’t think too clearly when under the spell of your salesmanship,” says Marion the librarian before bursting into song to profess her feelings for the charming, titular con man. The love story between Marion and Harold (Shirley Jones and Robert Preston) is the sunny backbone of this uplifting Midwestern musical, full of great music and great vibes.
If you prefer your romance movies spiked with action, comedy, and suspense, this flick is just the ticket. Bonus: “Charade” is the first and only time Cary Grant and Audrey Hepburn were paired together in a movie. (If you find it objectionable when a leading man is a quarter-century older than the leading lady, skip it.)
It’s the stage-to-film adaptation that makes you dance all night while repeatedly exclaiming, “The Rain in Spain stays mainly in the plain.” Falling in love with Eliza Doolittle is easy to do. But if it’s Audrey Hepburn’s singing that has you enraptured, sorry, that was ghost singer Marni Nixon.
This epic love story continues to tug at our heartstrings. “Yes, it’s old-fashioned and sappy,” reads a modern review. “But it’s impossible not to swoon.” Watching the film, one is reminded that love requires patience. The movie is three hours and 17 minutes long. In fact, the leading man (Omar Sharif) and leading lady (Julie Christie) don’t speak a word to each other until more than an hour into the film.
A little pick-me-up after “Dr. Zhivago,” this art-heist-themed comedy is as light and digestible as they come. Will partners in crime, played by Audrey Hepburn and Peter O’Toole, make for perfect partners in passion? Filmed in Paris, arguably the most romantic city in the world, the movie exudes sophistication and style.
Can love overcome prejudice? That’s the central question this dramedy tries to answer. While much of the film’s dialogue about interracial marriage might seem dated today, the enduring appeal of the movie is in the brilliance of its actors, including Sidney Potier, Katharine Hepburn, and Spencer Tracy, who bring an abundance of heart to their performances. Reflecting on the “Glory of Love” would be inevitable, even if it weren’t the movie’s theme song.
When Barbra Stresand sings about being in love, you believe her. Her spectacular Hollywood debut had her performing opposite talented playboy Omar Sharif. The chemistry between them was sizzling and, as it turns out, not entirely fictitious. Four years later, the actors made the optimistic choice to team up again for the movie’s sequel, “Funny Lady,” which, apologies, Babs, was a giant flop.
Who can resist a story about the transformative power of true love? British pop star Petula Clark, famous for songs like “Downtown” and “Don’t Sleep in the Subway,” starred with Peter O’Toole in this sentimental musical romance about a teacher who finds his footing after meeting the perfect partner. Clark and O’Toole’s have standout performances and a palpable connection.
“Love means never having to say you’re sorry.” So there’s no need to apologize for watching this heart-wrenching tearjerker about young lovers Jenny and Oliver (Ali MacGraw and Ryan O’Neal) over and over again. You know full well that you’ll be taken on an emotional rollercoaster each time, but it’s worth it. (Side note: Don’t get relationship advice from movies.)
“The past is a foreign country: They do things differently there.” Those are the famous first lines of this tragic love story, based on a 1953 novel. In the British period drama, a 12 year old is put in the awkward position of delivering letters between two illicit lovers and soon learns about the firm line between passion and expectation.
All eyes are on four identical plaid travel bags in this critically acclaimed comedy. But tucked into the screwball plot is an irresistible one-sided courtship between Judy and Howard, masterfully portrayed by Barbra Streisand and Ryan O’Neal. The absurdity of the story aside, the pair have chemistry.
On a roll with winning romantic roles, Barbra Streisand flexes her serious side in this melodrama with Robert Redford. The film’s Oscar-winning title song, sung by its star, sums up the principle question of the story: “If we had the chance to do it all again, tell me, would we?” Even when the answer is “no,” the memories can remain precious.
Ellen Burstyn won an Oscar for her role as the title character in this Martin Scorsese classic. The film’s poster marketed it as “a movie for everyone who has ever dreamed of a second chance.” Romantically speaking, when that second chance came in the form of a rugged rancher, played by the soulful Kris Kristofferson, the ladies in the audience had no complaints.
Apparently, romance was dead in Hollywood this year, with very few films released that would qualify as love stories. So, we turn to France for an edgy exploration of obsession and affection in this award-winning film, “L’important C’est D’Aimer.” The provocative plot centers around a middle-aged actress torn between her husband and a new sexual partner. An all-consuming desire for love threatens to ruin them all.
A star was born again and again and again and again. This edition, released in America’s bicentennial year, was the second remake of the 1937 film. The first remake was in 1954. And a fourth “A Star is Born” hit theaters in 2018. Putting aside the fact that this version was the least critically successful, the story itself is unquestionably full of passion and, clearly, stands the test of time.
Sure, “Annie Hall” won five Oscars and a lot of hearts in 1977. But, in case you’ve stopped watching Woody Allen movies, here’s an alternative, great romantic flick. It’s the story of a single mom who suddenly finds herself living with a stranger she can’t stand … at first. Neil Simon’s hilarious script and fine performances by Richard Dreyfuss and Marsha Mason just might make you forget how much you love and miss Diane Keaton.
Jon Voight and Jane Fonda both won Oscars for their moving roles in this Vietnam-era, romantic drama featuring an agonizing love triangle. If you’re looking for a romance movie with a lot less intensity and a lot more hair gel and fancy footwork, there’s always “Grease,” which also came out in 1978.
How could this 94-minute treasure not make the list when it features the big-screen debut of one of the most beloved couples in the history of American cinema: Miss Piggy and Kermit the Frog? Credit to Jim Henson for how quickly he convinced us that a porcine-amphibian romantic connection was plausible. Speaking of connections, this is the movie that brought the world the dreamy song “Rainbow Connection.” Oh, Kermie.
The bright lights of Houston lure a country boy to the honkytonk scene in this sexy film starring John Travolta and Debra Winger. The key relationship in the movie is weakened by flawed characters trying to control their tempers and manage their expectations. But the heat is real and the stellar soundtrack might very well get you in the mood to go “Lookin’ for Love” or a mechanical bull.
“Listen to me mister, you’re my knight in shining armour. Don’t you forget it! You’re going to get back on that horse. And I’m going to be right behind you, holding on tight. And away we’re going to go, go, go!” If you don’t get a lump in your throat when Katharine Hepburn says that to Henry Fonda, you might not have a pulse. Audiences were captivated by the film’s study of the staying power of a long, love-filled marriage, marvelously portrayed by two veteran actors. Incidentally, Hepburn and Ford had never performed together before.
In this iconic melodrama, Zack, played by Richard Gere, fumbles along the difficult path to becoming both an officer in the U.S. Navy and a gentleman in the eyes of Paula, played by Debra Winger. The charisma and talent of Gere and Winger are undeniable, and parts of the film were so steamy that editors had to get creative to keep the picture rated R instead of X. (That said, some fans might be surprised to learn that the two actors did not get along. Winger later compared Gere to a “brick wall.” Ouch.)
“If you wanted to get me on my back, all you had to do was ask,” quips Jack Nicholson to Shirley MacLaine in the Oscar-winning dramedy’s famous beach scene. There’s just a brief moment of romantic bliss between the two characters — a former astronaut and a socialite — before things get brilliantly messy and funny again. But a surprisingly touching relationship develops, however unstable.
Romance writer Joan Wilder (Kathleen Turner) travels to Colombia to save her sister from kidnappers, but she quickly finds herself in need of rescuing, too. Thankfully, help arrives in the form of jungle tough-guy Jack Colton (Michael Douglas), although he’s reluctant to get involved at first. (“What did you do, wake up this morning and say, ‘Today, I’m going to ruin a man’s life?’”) Hilarity, adventure, and, yes, romance ensue. The next year, Douglas and Turner tried their luck with a sequel, “Jewel of the Nile,” but that didn’t go so well.
Can people from two different worlds fall in love and make it work? And why are stories that pose that question so damn hot? Besides a little murder investigation, forbidden love is the main focus of this beautiful film starring Harrison Ford and Kelly McGillis.
When you feel the need for speed, or you’ve lost that loving feeling, this movie is there. A gorgeous, cunning flight instructor (Kelly McGillis) has much to teach the rebellious, aptly-nicknamed Maverick (Tom Cruise) in the classic ‘80s comedy-action-drama-tearjerker. Alas, 2022's “Top Gun: Maverick” was.a hit but not a reboot since McGillis was not asked to be in it. So much for that happily ever after.
This was a banner year for romantic movies. “Moonstruck,” “Roxanne,” and “The Princess Bride” were all also released in 1987, so it’s hard to pick the most romantic of the bunch. But there’s something about “Dirty Dancing” that checks all the right boxes: Patrick Swayze, check, check, check. Seriously though, while Swayze’s Johnny Castle is a dream, the story’s spark comes from the fact that it’s told from a young woman’s wide-eyed perspective. And when Johnny pulled Baby (Jennifer Grey) out of that corner and onto the stage to have the time of their lives, this little-movie-that-could solidified its place in our hearts.
Harrison Ford takes a break from raiding lost arks and defending the galaxy to charm Melanie Griffith in this ambition- and shoulder-pad-filled romantic comedy. The story is about a woman who pretends to be someone she’s not to see if she can get something she wants, a plot device we, apparently, couldn’t get enough of in the ‘80s. And if she happens to also get the guy in the process? All the better.
When Harry Burns met Sally Albright on the pages of screenwriter Nora Ephron’s enchanting script, pure romantic genius was the result. And her words fell into trusted hands when Billy Crystal and Meg Ryan took on the leads in one of the most adored love stories in cinematic history. Oh, and it’s funny — very, very funny. (Remember “I’ll have what she’s having”?) Shockingly, this flawless gem is only 91% fresh on Rotten Tomatoes.
When producers made the prophetic choices to lighten up a dark script and risk hiring rising star Julia Robers for the title role, this unlikely rom-com was off like a Lotus Esprit that corners on rails. The R-rated fairytale brought in $463.4 million at the box office. “Welcome to Hollywood! What’s your dream?” You want to make a romantic comedy about a sleazy businessman who falls for a prostitute? Go for it!
A more traditional fairytale, based on an old French folk story stole the spotlight the next year. The 30th feature film for Walt Disney Animation Studios won over audiences of all ages. It was the first animated movie to be nominated for a Best Picture Academy Award and it picked up two Oscars for its phenomenal music.
When Whitney Houston belted out Dolly Parton’s “I Will Always Love You,” her film debut was suddenly imbued with a heightened sense of romantic fervor. The song stayed on top of the charts for 14 weeks. “The Bodyguard” received iffy reviews, with most of the haters complaining that the plot was too predictable, but co-star Kevin Kostner remains starry-eyed about his time with Houston. “It was a really important moment in her life and her career, and we’ll always be locked together that way,” Kostner told “Good Morning America” in 2018. “I kissed her once for everyone in America, and I kissed her once for me, too.”
It’s natural to start to feel a little restless watching “Sleepless,” waiting on pins and needles for Sam (Tom Hanks) and Annie (Meg Ryan) to meet face-to-face. The leading characters only end up sharing about two minutes of screentime in the film, and yet all of the hopeless romantics in the audience are involuntarily drawn into both characters’ orbits, certain the union is written in the stars. “I smiled the whole way through,” wrote Roger Ebert.
The title alone is enough to hook you into this charming British ensemble film. (Who’s going to get married? Who’s going to die? Keep watching to see.) Of course, the other key reason to stick with the story is to discover how things turn out for heartbroken heartthrob Charles (Hugh Grant), who’s pining for Carrie, a beautiful, aloof American (Andie MacDowell). If Grant seems especially earnest in this film, it’s because it was his first big break — the movie that made him a rom-com legend.
Come for the witty banter and political commentary, stay for the utterly sweet love story. When the president of the United States (Michael Douglas) starts dating lobbyist Sydney Ellen Wade (Annette Benning), sparks fly but approval ratings drop. Can he win her heart and win re-election? And will he ever figure out a way to send her flowers?
Critics swooned over this powerfully romantic film, comparing it in significance to “Dr. Zhivago” and “Casablanca.” The mesmerizing adaptation of a 1992 novel scored a whopping nine Oscars. As the answers to the plot’s puzzles reveal themselves, the emotional impact of the characters’ intense pull for each other hits the audience hard.
Much like “The English Patient,” which features a dying man as the title character, everyone who went to see “Titanic” — an epic film triumph with 11 Oscars — knew what was going to happen, or at least we knew that damn iceberg could not be stopped. Still, we hoped against hope that the story’s darlings, Jack and Rose (Leonardo DiCaprio and Kate Winslet), would both find a lifeboat and their happy ending. Alas...
It paid to brush up on your Shakespeare before going to see “Shakespeare in Love.” Still, even if some of the jokes were over the heads of less literary-minded audience members, this romantic-comedy was pure joy for all. The perfect date-night movie even managed to pick up a Best Picture Oscar. (Clearly, we were craving a little levity after “The English Patient” and “Titanic.”)
Both Julia Roberts and co-star Hugh Grant were in their loveable heyday when they signed on for this ‘90s charmer. Roberts — who was reportedly paid $15 million for her performance — is, unsurprisingly, quite believable in her role as Hollywood megastar Anna Scott. Grant had to reach deeper to portray lowly London bookstore owner WIlliam Thacker. Anyway, it’s a delightful love story and the supporting characters are hilarious. (If the vibe of this film reminds you of “Four Weddings and a Funeral,” that makes sense— the two films share a lead actor, a screenwriter, and a producer.)
Obey the French, and indulge in chocolat! This Oscar-nominated, whimsical fable about love and lust presents the audience with plenty of cinematic eye candy and not-so-subtle life lessons. Anyone with an open heart will be seduced by its charms and the allure of its characters, especially the enchanting Vianne (Juliette Binoche).
