10 Things I Hate About You

A contemporary reimagining of Shakespeare’s Taming of the Shrew, this campus comedy from 1999 stars Julia Stiles opposite the late Heath Ledger. The two, though perfectly matched in their unyielding ethics and love of rock ’n’ roll, don’t fall for each other until they find themselves as pawns in a bet that might just be the best thing that’s ever happened to them.

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As Good As It Gets

A two-time Oscar winner (and seven-time nominee), James L. Brooks’s As Good As It Gets takes a road trip with the unlikeliest of trios: a waitress (Helen Hunt), an artist (Greg Kinnear), and a curmudgeon Jack Nicholson). It’s on this top-down excursion in a Saab convertible that each one embarks on a journey to self-acceptance, discovery, and, for two of them, love.

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Boomerang

A certified player (Eddie Murphy) gets a taste of his own bad medicine when he climbs into bed with his glamazon boss (Robin Givens). Brushed off and feeling rejected, Marcus gets a lesson in the game of love with Halle Berry’s Angela there to pick up the pieces. The best part though? The slew of rich comical performances courtesy of Eddie Murphy, David Alan Grier, Martin Lawrence, Chris Rock, and more.

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But I’m a Cheerleader

Director Jamie Babbit’s first film stars Natasha Lyonne as a high school cheerleader who doesn’t yet know she’s a lesbian. It’s not until she’s sent to a conversion camp to cure her “condition” that she comes out as queer. And even though the character is borrowed from Babbit’s own life, most of the film unfolds in a brightly colored fantasy land with a slew of vibrant supporting actors including RuPaul, Clea DuVall, and Melanie Lynskey.

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Chungking Express

By no means your run-of-the-mill rom-com, Wong Karwai’s Chungking Express is a genre-bending romantic crime comedy buoyed by the heft of the human condition that will make arthouse enthusiasts and Cassavetes fans swoons. The story unfolds in two narratives, each one following the love exploits of a policeman. One man carries on with a waitress; the other a seedy drug dealer in a blonde wig.

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Clueless

The fashion. The soundtrack. The vernacular. We’re not sure it gets better than Amy Heckerling’s will-live-in-infamy rom-com, Clueless. Starring Alicia Silverstone as Cher Horowitz, alongside Stacey Dash as Dionne and Brittany Murphy as Tai, the film is an ode to Jane Austen’s Emma, retooled for everyone from the ’90s cool kid to the more “ensemble-y challenged.”

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Four Weddings and a Funeral

Screenwriter Richard Curtis is an embarrassment of riches when it comes to quirky British comedy. There’s Love Actually, About Time, Bridget Jones’s Diary—not to mention his 1994 comedic delight. The film, about a British bachelor named Charles (Hugh Grant) who falls in love with an American woman named Carrie (Andie MacDowell), is so well written and polished you’d never know it was his very first.

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Groundhog Day

Often regarded as the best rom-com of all time by film critics, Groundhog Day sees Bill Murray at his comedic best. He plays Phil Connors, a misanthropic weatherman who can’t seem to shake off February 2. Stuck in a frigid time loop forcing Phil to relive the annual Groundhog Day event in Punxsutawney, Pennsylvania, this cult classic from director Harold Ramis is one to watch again, and again, and again.

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How Stella Got Her Groove Back

Angela Bassett, in a rut? Riiiight. Just go with it, though, and you’ll be rewarded with a fun, flirty rom-com about life, love, and sex after divorce. Bassett stars as the titular Stella, a successful stockbroker whose best friend (Whoopi Goldberg) convinces her to let her hair down in Jamaica. It’s there where she meets a man who looks like he jumped off the pages of a romance novel and, well, gets her groove back.

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Jeffrey

It’s 1995 and the scare of AIDS has taken all the fun out of sex for one gay man in New York City. So he goes celibate. That is, until he meets the man of his dreams at a gym and is forced to decide if love outweighs the risks of death. Single White Female’s Steven Weber stars as Jeffrey, with Patrick Stewart, Jeffrey Ross, Olympia Dukakis, and Sigourney Weaver making one helluva supporting cast.

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My Best Friend’s Wedding

Set in Chicago during peak baseball season, this ’90s gem stars the comedic chops of Julia Roberts and Cameron Diaz. Roberts plays Jules, a pessimistic food critic from New York City, while Diaz takes on Kim, the dazzling daddy’s girl who’s stolen the heart of Jules’s best friend, Michael. It’s only when she learns Michael and Kim are engaged that old feelings resurface and she plots to keep him for herself.

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Pretty Woman

Julia Roberts and Richard Gere bookend the '90s with a pair of rom-coms—Pretty Woman and Runaway Bride—that help define the decade, but it’s the former that will live rent free in the nostalgic corners of our minds. Roberts stars as Vivian, a working girl whose most recent score takes her from the corner of Sunset and Hollywood to the lap of luxury on Rodeo Drive; Gere costars as Edward, not to be nicknamed Eddie, the wallet funding her exploits and eventually falling for her charm.

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Sleepless in Seattle

After spending the ’80s penning some of the decade’s most iconic romantic comedies (Heartburn, When Harry Met Sally…), Nora Ephron gets behind the lens for a stream of comedies in the ’90s that includes Mixed Nuts, You’ve Got Mail, and Michael. The pinnacle of her ’90s contributions, though? Sleepless in Seattle, the story of man (Tom Hanks), a woman (Meg Ryan), and the Empire State Building.

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Sliding Doors

How any chump could ever betray Gwyneth Paltrow is beyond us, but, hey, suspension of disbelief, right? Here, she plays Helen, a woman whose life splits into two narratives: one in which she catches her loser boyfriend, Gerry, cheating, and the other where he narrowly escapes her discovery. An enchanting fantasy that plays with alternate realities, Sliding Doors may technically be two movies, but it’s also one wholly satisfying watch.

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The Best Man

Malcolm D. Lee struck gold with his 1999 cast. Bringing together Taye Diggs, Sanaa Lathan, Morris Chestnut, Nia Long, and so many more, The Best Man is a master class in onscreen chemistry. The story uncoils through Diggs’s Harper, a writer whose latest novel may or may not include salacious real-life details about a sexual encounter with the bride who’s walking down the aisle with his best friend.

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The Birdcage

Nathan Lane and Robin Williams give encore performances as Albert and Armand Goldman, a gay couple who play it straight to meet the conservative parents of the woman their son is about to marry. Directed by acclaimed helmer Mike Nichols, this screwball comedy has everything you want in a sidesplitting romp: legends milking every scene, dialogue that doesn’t miss, and a story that pushes the boundaries.

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The Wedding Banquet

You are cordially invited to laugh your ass off at Ang Lee’s 1993 rom-com about a gay Manhattan couple, Wai-Tung and Simon, who dodge outing their relationship to Wai-Tung’s parents by agreeing to a marriage of convenience between Wai-Tung and Wei-Wei, an immigrant Chinese woman who needs a green card. What could go wrong?

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The Wedding Singer

Adam Sandler gives his tonsils the stage in this totally ’80s wedding comedy. Joined by one of his frequent rom-com collaborators, Drew Barrymore, the funnyman cycles through hits of the decade including “Holiday,” “You Spin Me Round,” and “Love Stinks,” as lovers celebrate their “I dos,” finally realizing his dream girl is about to walk down the aisle with somebody else.

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The Wood

Narrated by Omar Epps’s Mike, The Wood is, yes, another wedding comedy, but more than a romance, it’s a bromance. When Taye Diggs’s Roland gets cold feet on his wedding day, his two buddies, Mike and Richard T. Jones’s Slim, work to warm him to the idea of marriage. A lighthearted journey from boyhood to manhood, their trip down memory lane is peppered with hilarious misadventures and more.

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Waiting to Exhale

Forest Whitaker makes his directorial debut with one of the best ensemble cast a filmmaker could ask for. Whitney Houston, Angela Bassett, Loretta Devine, and Lela Rochon join forces to bring Terry McMillan’s same-name novel to life, portraying the lives of four modern Black women navigating the minefield that is love and relationships.

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DeAnna Janes is a freelance writer and editor for a number of sites, including Harper’s BAZAAR, Tasting Table, Fast Company and Brit + Co, and is a passionate supporter of animal causes, copy savant, movie dork and reckless connoisseur of all holidays. A native Texan living in NYC since 2005, Janes has a degree in journalism from Texas A&M and  got her start in media at US Weekly before moving on to O Magazine, and eventually becoming the entertainment editor of the once-loved, now-shuttered DailyCandy. She’s based on the Upper West Side.

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