10. Green Card (1990)
Andie MacDowell remains a queen of 90s cinema. She appeared in several great movies of the era, and almost all were rom-coms—likeGreen Card, which has aged like a fine wine since its initial release in 1990.
It tells the story of a young woman who marries a French immigrant (without meeting him) so he will be able to stay in the US. But when their marriage ends up under investigation, the two strangers are forced to live together and learn about one another to fool the authorities.
Peter Weir’s picture is full of funny moments and great storytelling. Along with his other works,Green Cardhas the feeling of a story that’s slightly different to the norm, featuring passionate performances from both Andie MacDowell and Gerard Depardieu in their leading roles.
9. 10 Things I Hate About You (1999)
Armed with a precocious cast of pre-famous superstars,10 Things I Hate About Youis a teen angst movie based onThe Taming of the Shrew.
At first, Patrick Verona is paid to date the difficult-on-the-surface Kat Stratford—but as he does, he ends up seeing sides to her that nobody else knows about. The pair do battle with one another in many ways, all while falling hopelessly in love with each other.
Heath Ledger and Julia Stiles lead the cast with Joseph Gordon-Levitt in a supporting role, resulting in a movie that made their Hollywood careers and one that remains effortlessly charming over 20 years later.
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8. Pretty Woman (1990)
Getting its title from the famous Roy Orbison song,Pretty Womanbecame a 1990 hit as Julia Roberts and Richard Gere starred as an upbeat prostitute and the businessman she encounters by chance.
After Julia Roberts' Vivian shows Richard Gere’s Edward how to drive his car, they spend the night together in his hotel and strike a business deal: Vivian poses as his date for the various business functions Edward has to attend before leaving LA and going back to New York.
The film is still as fun today as it was 30 years ago, with Roberts and Gere praised for their roles (and Roberts earning an Oscar nomination).
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7. Notting Hill (1999)
Notting Hillfeels like a British film in every sense of the word: it’s small in scale, it’s packed with wit, and it stars Hugh Grant.
Written by Richard Curtis,Notting Hillcenters on William Thacker, a failing bookstore owner in West London who bumps into Hollywood megastar Anna Scott—and, despite just meeting her, they end up kissing.
Hugh Grant and Julia Roberts make the picture endlessly rewatchable, and it’s made even more rewatchable by the performances of the pitch-perfect supporting cast featuring Hugh Bonneville, Rhys Ifans, Emma Chambers, and Tim McInnerny.
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6. Clueless (1995)
Based on Jane Austen’s novelEmma,Cluelessis blessed with a whimsical script and iconic performances from Alicia Silverstone and Paul Rudd.
The movie follows Cher (the pampered high school daughter of a high-price lawyer) and her attempts to make everyone around her dance to her tune. What makes the film so likable is that she isn’t a horrible person—she wants to help people in her own way, but she’s simply misguided.
Paul Rudd and Alicia Silverstone’s chemistry is some of the best in 90s rom-com as they fall in love slowly and without knowing it.
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5. While You Were Sleeping (1995)
Of the many great stars to come out of 90s rom-coms, Sandra Bullock is the one who had the most charm that simply oozed on screen.
While You Were Sleepingis evidence of this. As Bullock’s character Lucy is accidentally mistaken for the fiancée of a man in a coma, she falls in love with his kind and loving family—also his brother, Jack.
Bullock’s outing here is perhaps the sweetest and most heartwarming performance ever given in a rom-com. With Bill Pullman as her love interest, the movie became a 90s classic.
4. Sleepless in Seattle (1993)
Tom Hanks and Meg Ryan’s chemistry in only a handful of scenes together was such a hit with audiences that they became iconic as a rom-com duo—all because ofSleepless in Seattle.
Nora Ephron’s brilliant script sees two people from different parts of the US fall in love without speaking: after Tom Hanks' Sam loses his wife, his young son calls a radio station and tells their story to the whole country—with Meg Ryan’s Annie Reed listening from her car.
Sleepless in Seattleis a heartbreaking yet heartwarming ride, with good people not entirely getting what they want due to an attraction that spans the continental United States. However, the true skill here is Ephron’s ability to keep the story flowing without tonal shifts.
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3. Four Weddings and a Funeral (1994)
Four Weddings and a Funeralis at first a brilliant comedy and at last a heartbreaking melody on the impermanence of love. Starring Andie MacDowell and Hugh Grant, it follows a bunch of young 30-somethings as all their friends start getting married.
When Charles (played by Hugh Grant) meets Carrie (played by Andie MacDowell) at a wedding, they instantly have a love connection—which both of them try to forget about since she’s engaged to be married.
Richard Curtis' film was nominated for Best Picture and Best Original Screenplay at the Academy Awards, while Hugh Grant won a Golden Globe and a BAFTA for his performance.
2. Groundhog Day (1993)
Some films are timeless classics. Other films are elevated to a whole new status altogether, as in the case ofGroundhog Day.
The story follows a weatherman named Phil after he finds himself stuck in a time loop, reliving the same day over again for decades. He’s marooned in the town of Punxsutawney on Groundhog Day as a selfish and self-important character who’s unable to die despite numerous attempts.
Over time, Phil becomes a better person and stops thinking that his life is the most important one in the entire world, slowly changing his selfish ways with every repeated day. He also falls in love with his producer, Rita (played by the queen of rom-coms, Andie MacDowell).
The film remains one of the best comedy movies ever made, and Bill Murray’s leading performance is legendary.
Related:The Best Time Loop Movies Like Groundhog Day
1. As Good as It Gets (1997)
Few things are better in rom-com cinema history than Jack Nicholson and Helen Hunt sitting at a dinner table as he tries to find a compliment good enough to keep her from walking out.
As Good as It Getstells the tale of Melvin Udall, an OCD writer who’s bothered by his homosexual neighbor Simon and has a crush on the waitress who always serves him. However, after his neighbor is savagely beaten and robbed, Melvin starts caring for him and his dog.
With his own life turned upside down, Melvin can’t function properly—and meanwhile he and the waitress Carol begin a strange relationship as they accompany Simon on a road trip to see Simon’s estranged parents.
Jack Nicholson and Helen Hunt walked away with Academy Awards for their performances inAs Good as It Gets, with Greg Kinnear garnering a nomination for Supporting Actor. The film itself has become a rom-com icon in its own right and is a must-watch to this day.
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