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50 Classic Hollywood Romances You Shouldn't Miss

From the advent of the "talkies" to that faked orgasm.

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Most classic movies involve some kind of love story that's central to the plot. Heck, even Hitchcock movies had their fair share of smoochin'. But after a long cinematic dry spell, it's safe to say the resurgence of rom-coms upon us, thanks to films like To All the Boys I've Loved Before and Crazy Rich Asians. With so much love on the brain, we decided to investigate which classic films hold up as the most quintessentially romantic of them all. (And if you're looking for more, we also ranked the best romance movies of 2020 and the best rom-coms of all time.)

After scouring the archives of film history, we determined that the 50 movies below tell the story of rom-coms from the beginning of talking films through 1989 (we figured "classic" meant pre-1990—mainly because we just had to include When Harry Met Sally). So what other romantic movies do you simply have to see before you can truly call yourself an expert on the genre? Read on to see what made the cut.

City Lights (1931)

city lights
City Light's
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Charlie Chaplin's classic character The Tramp finds his new love connection with a blind flower girl (Virginia Cherrill) in jeopardy when she mistakes him as a famous millionaire playboy. City Lights, like the other films in Chaplin's repertoire, is a silent movie, but it's "aww" factor is still seriously strong.

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It Happened One Night (1934)

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It Happened One Night
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Considered one of the first and still greatest romantic comedies of all time, this Frank Capra joint stars Claudette Colbert as a feisty young heiress set to marry a man her father disapproves of and Clark Gable as the guy hired to help her get home. Guess whether they end up together? The chemistry between Colbert and Gable sizzles.

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A Tale of Two Cities (1935)

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Sure, it's the film adaptation of the classic Dickens novel you were forced to read in high school English class, but how can you not be utterly riveted by this story of morality, loss, and revolution in 18th century Europe? Also, Sydney Carton is a total unsung babe, here played by Ronald Colman. It won’t help you ace the test if you didn’t read the book, but consider the movie extra credit.

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Bringing Up Baby (1938)

cary grant and katharine hepburn in bringing up baby
Bringing Up Baby
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Cary Grant (who will appear many times on this list) and Katharine Hepburn (likewise) star in this truly batshit screwball comedy about a paleontologist and the woman who's into him. There are dinosaur bones, museum capers, and even a real-life leopard. Strap in.

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The Philadelphia Story (1940)

"the philadelphia story" film still
The Philadelphia Story
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The keystone in the “comedy of remarriage” genre—in which the characters of Code-era movies had to be divorced (rather than merely single) in order to make on-screen flirting kosher for audiences—is this movie starring Katharine Hepburn, Jimmy Stewart, and Cary Grant. Never mind their genuinely conflicting love triangle: Those three names alone qualify this movie for a spot on every list of top classic films.

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The Shop Around the Corner (1940)

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The Shop Around the Corner
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A delightful film from iconic director Ernst Lubitsch, this movie about pen-pals who turn out to be work rivals is just heart-wrenchingly romantic. Also, it’s the basis for 1998's You’ve Got Mail (hence the name of Kathleen Kelly’s bookstore, The Shop Around the Corner). Cross-generational swoon!

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His Girl Friday (1940)

"his girl friday" film still
His Girl Friday
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Cary Grant is a newspaper editor, and Rosalind Russell is the do-what-it-takes investigative reporter who used to date him. When he finds out she’s engaged to someone new, he tries to postpone the wedding by giving her a juicy story about a man who may be wrongfully convicted; she ends up getting in deep when the piece turns out to have more merit than they realized. Come for the proto-feminist messaging, stay for the lightning-quick dialogue. (Seriously, how do they talk this fast?)

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The Lady Eve (1941)

temptress eve
The Lady Eve
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Barbara Stanwyck plays Jean Harrington, a con artist known to prey on super-wealthy guys like Charles Pike (played by Henry Ford.) Jean thinks she has this one in the bag as she finds Charles falling under her spell, but soon this quick job gets complicated when he dumps her, assuming she's only after his money. Classic! The only possible solution? Re-introducing herself to Charles, but this time as high-society woman Lady Eve Sidwich.

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Casablanca (1942)

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There’s a reason this is considered one of the best films of all time. Humphrey Bogart scorches the screen while Ingrid Bergman is enchanting in a breathlessly romantic and genuinely funny epic about Morocco during WWII. Somehow the most quoted movie ever made is still surprising every time.

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Meet Me in St. Louis (1944)

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Meet Me in St. Louis
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Judy Garland stars in this musical romance about four sisters preparing for the 1904 World’s Fair in St. Louis, Missouri. Not only is it preciously cute with some impressive ensemble song-and-dance numbers, but this is also the movie that introduced to the world the classic holiday tune “Have Yourself a Merry Little Christmas.” That makes it both a rom-com and a Christmas movie—two great tastes that go great together (just ask Love Actually).

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An American in Paris (1951)

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An American in Paris
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Gene Kelly sings Gershwin tunes as a painter in Paris, where he surrounds himself with other bohemians and fawns over a beautiful ballet dancer. It was Leslie Caron’s first role in a movie, though she would go on to become a huge star (and the titular character in another romance on this list, Gigi).

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Singin’ in the Rain (1952)

kelly in 'singin'  in the rain'
Singin
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Debbie Reynolds danced until her feet bled, and Gene Kelly filmed the famous song sequence—you know, the one where he sings in the rain?—with a 103° fever, but it was all worth it for one of the greatest and most successful musicals ever made. Set during the transition from silent film to the “talkies,” Don (Kelly) and Lina (Jean Hagen) are actors whose newest film is remade into a musical. Don’s voice is perfectly fine, Lina’s is not. Enter aspiring actress Kathy Selden (Reynolds) to dub over Lina’s shrill in order to save the movie and their careers, with just a dash of love along the way.

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Roman Holiday (1953)

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Roman Holiday
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Audrey Hepburn and Gregory Peck star in this William Wyler–directed romance about a princess who takes a day off to run around town, and the civilian who falls for her. If you like Vespas, you’ll love this movie—even if Meghan Markle would have never.

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Seven Brides for Seven Brothers (1954)

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The premise of this particular Hollywood classic is pretty problematic (a band of rowdy brothers in the woods literally kidnap a group of women to make them their wives), but if you can look past the film's low-key Stockholm syndrome vibe, Seven Brides for Seven Brothers will be a good time. The bubbly soundtrack and fabulous choreography helps...kinda.

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Carmen Jones (1954)

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Carmen Jones
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Dorothy Dandridge's crazy good performance as Carmen Jones got her nominated for an Oscar, making history as the first African American actress in a leading role to be nominated. This crazy underrated musical set at an all-black army camp follows Carmen, who wants the super married Joe, so this should end well!

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Desk Set (1957)

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Dark Set
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A classic Battle of the Sexes comedy and the eighth film of famed acting couple Spencer Tracy and Katharine Hepburn. She’s a researcher at a broadcasting network who knows all the answers, he’s the computer salesman trying to put her out of a job. Madness and some hilarious-in-retrospect observations about the nature of technology ensue.

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An Affair to Remember (1957)

an affair to remember
An Affair to Remember
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Raise your hand if you’ve ever made a pact to reunite with someone on top of the Empire State Building in six months? Cary Grant’s character and Deborah Kerr’s character meet aboard the SS Constitution en route from Europe to New York, where they fall in love and make a plan to meet atop the Empire State Building, after which they’ll presumably ride off into the sunset. Spoiler: That’s not what winds up happening. But man, this is a love story for the ages.

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Funny Face (1957)

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Not to be confused with the 1927 musical of the same name that also starred Fred Astaire, this Funny Face features the dance icon as Dick Avery, a famed fashion photographer who finds the next big thing in a hesitant beauty named Jo Stockton (a delightfully snarky Audrey Hepburn). Romantic shenanigans and musical numbers ensue.

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Gigi (1958)

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Gigi
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This très charmant musical about a French womanizer and his teenage friend who grows up to become a hot lady is a master class in getting out the friend zone. It’s a wonderfully sweet film, at least if you pretend the song “Thank Heaven For Little Girls” isn’t in it.

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Some Like It Hot (1959)

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Some Like It Hot
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A classic film list without one film starring the iconic Marilyn Monroe would be a travesty! What's not a travesty, though? Her role as Sugar Kane, a member of an all-girl band set to perform for a couple of weeks in Florida, in Some Like It Hot. The singer befriends Joe (Tony Curtis) and Jerry (Jack Lemmon), two struggling musicians disguised as women on the run from a Chicago mob. The threesome looks like they'll be friends forever, but soon Joe finds himself falling for Sugar while Jerry tries to get rid of a millionaire bachelor who can't seem to take no for an answer. Just another day in paradise, I guess.

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West Side Story (1961)

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West Side Story
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If you like movie musicals, gang fights that involve a lot of finger-snapping, stories based on Romeo and Juliet, old school New York settings, and deeply unhappy endings, then West Side Story is the movie for you!

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Breakfast at Tiffany’s (1961)

Breakfast at Tiffany’s
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Audrey Hepburn is the O.G. Manic Pixie Dream Girl as Holly Golightly, the country bumpkin-turned-wild party girl living out her New York City fantasy and taking on some seriously odd jobs and eating pastries in front of the Tiffany's jewelry store. Yes, it’s a romance, but it’s also a movie about what it means to invent yourself. The most unrealistic aspect is probably that Audrey Hepburn eats carbohydrates daily, but as I recall I think we both kind of liked it.

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Paris Blues (1961)

paris blues
Paris Blues
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Paul Newman and Sidney Poitier are the leading men of this 1961 romantic drama that follows the professional and personal struggles of two aspiring American musicians trying to make it in France. The film, which is less "laugh out loud" than it is *deep sigh*, stirred controversy for its progressive portrayal of interracial relationships, reminding us that the days of Jim Crow weren't actually that long ago.

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Charade (1963)

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Charade
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Even decades after its release, the twists and turns in this story of a woman who teams up with a worldly playboy to solve her husband’s murder will keep you guessing until the very end. Cary Grant and Audrey Hepburn star in this caper that’s got as many thrills as it does swoon-worthy moments.

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My Fair Lady (1964)

audrey hepburn and rex harrison in my fair lady
My Fair Lady
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Based quite closely on George Bernard Shaw’s play Pygmalion, this musical follows the tale of a snobbish linguist (Rex Harrison, as a zaddy) who bets that he can turn a rough-and-tumble flower girl (Audrey Hepburn, as an urchin) into a high society lady. She's Audrey Hepburn so, naturally, she pulls it off.

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The Americanization of Emily (1964)

the americanization of emily
The Americanization of Emily
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James Garner plays an American WWII naval officer who usually chills on the sidelines at his buddies flat in London, and away from the action of the battlefield. While hiding, he meets Emily, played by Julie Andrews, a British woman recently widowed. They fall quickly in love, but Garner's character soon has to go on a dangerous mission that could risk everything they've built.

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How to Steal a Million (1966)

on the set of how to steal a million
How to Steal a Million
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Romantic heists should really be a more common genre in 2019, and this movie proves why. It’s about an art forger’s daughter (played by Audrey Hepburn, in the most divine Givenchy wardrobe) who falls in love with an art thief. Things get even screwier, but it’s hilarious, madcap, and butterflies-in-your-stomach romantic, too.

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Guess Who’s Coming to Dinner? (1967)

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Unsurprisingly, some things about this movie are super problematic today. For example. the minor characters are basically offensive stereotypes. But this 1967 romantic comedy was groundbreaking for its time. When white Joanna Drayton brings her black fiancé (played by the legendary Sidney Poitier) home to her wealthy liberal parents for the first time, they’re forced to reconcile their “liberal” ideations with their reservations about the then-controversial concept of interracial marriage. It’s an examination of race relations in the 1960s, released just six months after the landmark Loving v. Virginia case struck down anti-miscegenation laws in the United States.

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Romeo and Juliet (1968)

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Romeo and Juliet
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There are many adaptations of Romeo and Juliet, but only one that follows the text precisely while also bringing an awkwardly horny je ne sais quoi. This is the version you probably watched in your freshman year English class, and for that it is an instant classic. Also, great script. That Shakespeare guy was pretty good at writing!

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For Love of Ivy (1968)

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For Love of Ivy
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When a young black woman (Abbey Lincoln) decides to quit her job as a maid in order to pursue an education at a secretarial school, her employers freak out at the thought of losing her. Desperate, they hire a dashing executive (Sidney Poitier) to woo her and convince her to stay, but their boyfriend-for-hire's complicated personal life threatens to tear the entire scheme apart at the seams.

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Harold and Maude (1971)

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Harold and Maude
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This is a deeply strange, ultimately charming love story about a morbid young man who falls for a much, much older woman. If you want to understand Wes Anderson’s whole aesthetic, watch this movie—even if you don’t want to think too hard about whether Harold and Maude actually do the deed.

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The Way We Were (1973)

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The Way We Were
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Told via flashback, The Way We Were is a love story that almost isn’t. It’s not a spoiler to say this one doesn’t have a happy ending (remember the extended reference to it in Sex and the City?). It follows the lives of two polar opposites who wind up in a relationship: Katie, a politically-active Jewish woman played by Barbra Streisand, and Hubbell, an easy-going WASP played by Robert Redford. Their relationship is passionate and challenging and they almost go all the way.... Yeah, it’s a tearjerker.

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Claudine (1974)

claudine
Claudine
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A single working mother of six in Harlem, Claudine has no time for romance, but a chance encounter with neighborhood garbage collector, Roop, makes her eager to experience love again. Starring Diahann Carroll and James "The Voice" Earl Jones, Claudine tells the story of how love can grow even in the hardest of times.

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The Goodbye Girl (1977)

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Richard Dreyfuss won an Oscar for his performance as a struggling actor who sublets his friend’s apartment, only to find out that his friend has abandoned his girlfriend (Marsha Mason) and her 10-year-old daughter, who happen to still live there. The pair clash initially, but eventually get past their differences and sparks fly. It’s very 70s—and endlessly charming.

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Grease (1978)

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Grease
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Olivia Newton-John and John Travolta have famous chemistry in this tale of love between a bad boy and a good girl in the 1950s. They meet on the beach, fall in love, and then Danny Zuko thinks Sandy moves back to Australia at the end of the summer. But—TWIST!—she’s enrolled in his own Rydell High School for her senior year, and he’s suddenly got to reconcile his bad boy rep with the sweet, romantic guy Sandy met on the beach…in song!

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Tootsie (1982)

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Tootsie
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It shouldn’t be so hard to get men to respect women, but Dustin Hoffman famously admitted that appearing in Tootsie gave him perspective about how bad women have it in the workplace. He stars as Michael Dorsey, an unemployed actor with a terrible reputation who dresses up as a woman named Dorothy to help his friend’s play and winds up landing a role on a soap opera—in drag. Where’s the romance, you ask? The amazing love…rhombus (?), involving Michael, Michael’s female friend-with-benefits, the female co-star he falls in love with (Jessica Lange in an Oscar-winning performance), that same co-star's father, and a male co-star who is pining after Dorothy. Phew!

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An Officer and a Gentleman (1982)

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Before we're drooling (and then later questioning) Richard Gere's character in Pretty Woman, audiences everyone fell in love with him as Zack Mayo, a man aspiring to be a navy pilot. While at his 13-week training camp, he meets working girl Paula Pokrifi (Debra Winger) but gets warned of the working girl's hidden agendas of wanting to get married/pregnant to avoid a life of 9 to 5. While yes, that assumption is deeply problematic, the ending of this movie makes up for it and proves just maybe all guys in 1982 weren't the same. Just get ready to swoon.

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Splash (1984)

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Before ladies were boning fish—and I don’t mean for culinary purposes—in Oscar-nominated dramas directed by Guillermo del Toro, there was Splash, in which business guy Tom Hanks falls in love with a mermaid played by Daryl Hannah. It’s very 1980s, but Hanks is, as always, instantly lovable.

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Romancing the Stone (1984)

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Full of both romance and adventure, Romancing the Stone is basically Indiana Jones as a love story. Kathleen Turner plays a dowdy romance novelist who—after her sister is kidnapped by thugs in the Colombian jungle—discovers her own life is in danger and must bring a treasure map to her sister’s captors. She’s assisted by a gruff mercenary (Michael Douglas) who helps her find the treasure. It’s also hilarious, and Turner and Douglas are pitch-perfect.

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Sixteen Candles (1984)

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At the height of her Teen Queen status, Molly Ringwald starred as Samantha, a girl whose 16th birthday has pretty much been overlooked and overshadowed by her sister’s upcoming wedding. Not only that, she’s pining over older hottie Jake Ryan (the de facto name for every Hot Guy In High School) who doesn’t even know she’s alive, and the only boy in who seems to be interested in her is a massive dweeb. Yes, parts of it are super racist and problematic, but it’s also a true testament to the awkwardness of being 16 and hoping someone will see you.

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A Room With a View (1985)

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A Room With a View
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Based on the novel by E.M. Forster, this Merchant Ivory film about a couple of classy British ladies in Florence who come around to more modern thinking, thanks to Daniel Day-Lewis’s incredible ass (also other things about him and the world), is the definition of a horny period drama. More of these in the future, please!

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She’s Gotta Have It (1986)

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This story about a woman refusing to choose monogamy was the first full-length film for Spike Lee, who wrote and directed it. Though not as iconic as Lee’s Do The Right Thing (which came out three years later), it launched his career and was even remade into a very modern Netflix series in 2018.

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Baby Boom (1987)

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One of the first blockbuster Nancy Meyers screenplays, Baby Boom features Diane Keaton as a hard-nosed New York City business lady who inherits a baby girl and decides to move to the country. But even rural Vermont and its hot veterinarians played by Sam Shepard can't keep her killer business instincts down. This is as much a feminist tale as it is a romance, and is actually a reboot we'd want to see.

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Broadcast News (1987)

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Broadcast News
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Though today it’s mostly just people in suits reading other people’s tweets, broadcast news used to be quite a thing back in the 1980s. That's perfectly encapsulated in this hilarious James L. Brooks rom-com about a love triangle between journalists (played by William Hurt, Holly Hunter, and Albert Brooks).

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Moonstruck (1987)

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Moonstruck
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A beautiful widow (Cher, in a role for which she very rightly won a Best Actress Oscar) who lives with her Italian family in Brooklyn meets a tempestuous baker (Nic Cage, minus one hand) who turns out to be the estranged brother of her new fiancé, who happens to be visiting his ailing mother back in Sicily. It’s laugh-out-loud funny and sexy in a weird way, but the writing is deceptively poignant and thoughtful.

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The Princess Bride (1987)

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The ultimate romantic fairytale is also one of the funniest movies of the 1980s. Sure, Princess Buttercup and Wesley are made for each other, but Mandy Patinkin isn’t even in the main love story and he’s totally smoochable as Inigo Montoya. It’s almost impressive how well the jokes here hold up even 30 years after its initial release.

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Coming to America (1988)

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Before there was Wakanda, there was Zamunda, the wealthy African nation where Crown Prince Akeem Joffer (Eddie Murphy) is dreading his upcoming arranged marriage. He doesn’t want a woman who wants him because he’s a prince, he wants a woman who wants him for him. So what happens? He and his best friend go the New York, where Akeem gets a job at a fast-food restaurant and embarks on finding the woman of his dreams against his parents’ wishes. Plus, when it came out, black actors weren’t often romantic leads in film, which just adds to the importance and poignancy of this movie.

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Look Who's Talking (1989)

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Look Who's Talking
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As if the classic will-they-or-won't-they between Mollie (Kirstie Alley) and James (John Travolta) in Look Who's Talking isn't cute enough, the presence of totally adorable toddler Mikey as the story's omnipresent narrator really ups the ante as far as rom-coms go. Be careful with this one—your baby fever is definitely going to flare up.

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Say Anything… (1989)

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Yeah, yeah, yeah, everyone thinks of this movie as “John Cusack with the boombox,” but there’s a reason it makes every “best romantic comedies” list: It’s a love story on multiple levels and shows just how much people will endure for love. John Cusack stars as Lloyd Dobler, an slacker/aspiring kickboxer in love with Ione Skye’s Diane Court, the class valedictorian. Classic.

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When Harry Met Sally (1989)

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Can men and women ever really be friends? This movie doesn’t make a case for the likelihood, but Billy Crystal is sarcastically sexy and Meg Ryan is peak-America’s Sweetheart. In addition to all the iconic comedy scenes, it still manages to be incredibly sweet and romantic. I’ll have what they’re having.

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