10 Romantic Comedies from the 90s Worth Revisiting

Singles has two great things going for it: the Seattle grunge setting and a strong ensemble cast including Bridget Fonda, Kyra Sedgwick, and a long-haired Matt Dillon. Most of the characters are neighbors in an apartment complex, the kind of place where friends just climb in through each other’s windows to say hi. To top it off, there’s the line Campbell Scott’s adorable character Steve says: “I just happened to be … nowhere near your neighborhood.”

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Some rom-coms tend to be more rom than com, but this hilarious British film keeps me laughing every time I watch it. And of course, no list of romantic comedies is complete without a Hugh Grant film, and here he’s in top form: cute, bumbling, prone to heinous faux pas, and completely smitten with the American woman (Andie MacDowell) he keeps running into at various weddings. 

This '90s gem is a romance tailor-made for Gen X, complete with existential crises and cigarettes. Winona Ryder plays Lelaina, a woman struggling with work, love, and friendship fresh out of college. She’s making a documentary about her friends, and is caught in a love triangle between yuppie Michael (Ben Stiller) and her emotionally unavailable slacker friend Troy (Ethan Hawke). Janeane Garofalo as Lelaina’s bestie Vickie is the sarcastic icing on the cake.

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Likable Sandra Bullock has never been more endearing than in her role as unlucky-in-love token collector Lucy. After crushing on the perfect man from afar, Lucy ends up rescuing him when he falls on the train tracks. She ends up at his bedside while he’s in a coma, and—through a plot twist that could only happen in a movie—his family assumes that she’s his fiancée. Bill Pullman is surprisingly sexy here as the man who eventually wins Lucy’s heart. Between the misunderstandings, family hilarity, and walks through the snow, holiday romance doesn’t get much better than this.

Nothing says the late 90s like Kevin Smith, and Chasing Amy is arguably one of his best films. Here he tackles friendship, romance, and sexuality in surprising ways with the complicated romance that starts when comic book artist Holden (Ben Affleck) meets Alyssa (Joey Lauren Adams), a fellow artist and a lesbian. Chasing Amy is probably the most bittersweet love story on this list, but worth revisiting for the raunchy humor and thoughtful examination of women’s sexuality, male insecurity, and complex relationships.

Sometimes I need a dose of dead bodies along with a love story, and for those times there’s this John Cusack gem. Here Cusack plays Martin, a hit man home for his high school reunion. Although the movie is ostensibly a crime comedy, it has a big dose of second-chance romance: once Martin returns home, he focuses on reuniting with his former girlfriend, Debi (Minnie Driver). Unfortunately, his next target is her dad. Along with deliciously dry humor, the romance is playful and ends happily, and the hit man jokes keep coming—especially as Martin repeatedly tells his old classmates what he really does for a living and they all assume he’s kidding…until the guns start going off.

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You can’t get a more perfect rom-com pairing than Tom Hanks and Meg Ryan. Of course the two were great in that other 90s romance, Sleepless in Seattle; but You’ve Got Mail brings romance along with a heap of 90s nostalgia (I mean, who has AOL email anymore?) in this remake of 1940’s The Shop Around the Corner. She’s a struggling bookseller, he’s the cocky exec that clashes with her. Meanwhile they’re falling in love with each other’s anonymous personas online, but like with Sleepless, you just want them to ditch the plot device and meet already.

This sexy, drama-filled wedding movie stars Taye Diggs as a writer who’s nervous about committing to his girlfriend Robin (the fantastic Sanaa Lathan). At a wedding among old friends, he’s tempted by Robin (Nia Long), even though she’s about to marry his friend. The film is hot in more ways than one—as secrets and passions come out, tempers flare, fists fly, and somewhere in there Taye Diggs is in a bathtub surrounded by candles.

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Though people don’t really use the phrase “all that” much anymore, in the late 90s, this film was all that for me, and more. My friends and I had many repeat viewings of it throughout college because it had the perfect recipe for a high school rom-com: take a popular jock (Freddie Prinze, Jr.) who accepts a bet to transform an artsy nerd (Rachael Leigh Cook) into prom queen. Add in a soundtrack that includes such 90s hits as Sixpence None the Richer’s “Kiss Me.” Finally, top it off with a prom scene where the high schoolers randomly break into a choreographed dance to “The Rockafeller Skank.” Sure, it’s a little cheesy, but you’d be hard-pressed to find a more nostalgia-filled romance.

Shakespeare has never been so hilariously romantic as this 90s retelling of The Taming of the Shrew set among high schoolers. Bianca can’t start dating until her cranky older sister, Katarina (Julia Stiles) does. So one of Bianca's suitors pays bad boy Patrick (Heath Ledger) to seduce Kat. As far as grand gestures go, it doesn’t get much better than Heath Ledger singing “I Can’t Take My Eyes Off You” while dancing on the bleachers.

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