The 15 Best '90s Rom-Coms to Watch On Repeat
Murder docs and psychological thrillers are all the rage right now. (Case in point: We can hardly open Instagram without seeing Penn Badgley memes all over our feeds.) But if you've gone down a dark hole on Netflix and need to find the light, you can always turn to a good old '90s rom-com for the mood lift you need. Bonus: You'll find plenty of '90s nostalgia and fashion inspo to replace the void in your life ever since Friends left Netflix last month.
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Sure, romance in 2020 may look a bit different than it did back in the days before smartphones, but it's all the more reason to cue up one of these rom-coms on a Friday night and forget all your modern-day dating and technology woes. (And I mean, is anything more delightful than watching the rom-com king and queen — Meg Ryan and Tom Hanks, duh — fall in love over and over again?)
Here, the best '90s rom-coms to check-out — or to revisit because, let’s face it, these classics are designed to be watched over and over again until you can memorize every line. The hardest part will be deciding which one to choose first.
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1. Pretty Woman
You know the storyline: Vivian (Julia Roberts) charms a wealthy businessman (Richard Gere) and puts a snarky shopping clerk in her place. (“You work on commission, right? Big mistake. Big. Huge.”) Sure, the themes may not hold up as well in 2020 (partially why the Broadway adaptation failed to garner the same opening success as the movie did back in 1990), but let’s be honest, Julia Roberts’s infectious laugh is timeless.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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2. Sleepless in Seattle
Forget dating apps — in this rom-com, Baltimore Sun reporter Annie (aka Meg Ryan) is connected with Seattle-based widower (aka Tom Hanks) through the radio and then write each other actual love letters. Watch as the two leap hurdles to find one another — leading them both to the top of the Empire State Building on Valentine's Day. Pure onscreen magic.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
3. Clueless
Is it really a '90s round-up without this 1995 hit? “Ugh! As if!” The fashion moments in this movie are iconic — like when popular Beverly Hills teenager Cher (Alicia Silverstone) and best friend Dionne (Stacey Dash) decide to give Tai (Brittany Murphy), the “tragically unhip” new girl at school a makeover. While some may argue this is more of a teen coming-of-age comedy than a true rom-com, we beg to differ: Not only does Cher play matchmaker with her teachers, but who could forget the long-awaited kissing scene on the stairs between Cher and her former stepbrother (the ageless Paul Rudd) at the end?!
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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4. She’s All That
You’ve heard the one about the popular guy (Freddie Prinze Jr.) who takes a bet to turn the not-so-popular girl (Rachael Leigh Cook) into the prom queen, right? She takes off her glasses and, boom, she’s the dream girl he’s been waiting for — but does she feel the same? Yeah, that’s a 90s rom-com if there ever was one.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
5. There’s Something About Mary
It’s been several years since Ted’s (Ben Stiller) prom date with Mary (Cameron Diaz) didn’t happen as the result of an embarrassing, um, injury that occurred before the dance — and now he wants to try and reconnect with her. Ted hires a private investigator (played by Matt Dillon) to find Mary, but when he does, he lies to Ted so that he can try to date her himself. Ted tries to win over Mary anyway and, well, the results are pretty hilarious, including one rather notorious scene where Mary uses a special kind of "hair gel," shall we say, that keeps her hair rather coiffed.
Available to stream on Hulu (with CINEMAX add-on), iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
6. 10 Things I Hate About You
Working as a loose adaptation of William Shakespeare's Taming of the Shrew, this movie features the Stratford sisters, Kat (Julia Stiles) and Bianca (Larisa Oleynik). The girls’ dad has set a house rule that Bianca, a social butterfly, can’t date until Kat has a boyfriend. One problem: Kat isn’t exactly interested. That is, of course, until she crosses paths with Patrick Verona (Heath Ledger). And, really, if you don’t cry when Julia Stiles delivers her “But mostly I hate the way I don't hate you, not even close… not even a little bit… not even at all” lines and her chin begins to quiver, then are you really even watching?
Available to stream on Disney+, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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7. Can’t Hardly Wait
What happens when school’s out and everyone in your high school gets together for one big party? Well, the result is this 1998 teen rom-com, featuring a crew of high school tropes, including popular Amanda (Jennifer Love Hewitt), artsy Preston (Ethan Embry), rapper wannabe (Seth Green), and football star Mike (Peter Facinelli). And, OK, if the high school you still yearns for a victory teenage story where the popular girl ends up being nice and the not-so-popular guy scores the girl of his dreams (and the stereotypical meathead ends up aging appropriately), well, then this is the movie for you.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
8. Runaway Bride
Runaway Bride is another opportunity to catch the unmatched electricity between Julia Roberts and Richard Gere. In case you forgot, Roberts plays a witty woman who has left three grooms at the altar — prompting a reporter (Richard Gere, duh) to write a story about her. He’s divorced, jaded, and completely immune to Maggie’s charms.... or is he? Plus, if you've ever wondered what your egg order has to do with your level of independence, Runaway Bride has the inside scoop.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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9. The Best Man
This 1999 rom-com features a young Taye Diggs — which really should be enough said. Diggs plays Harper, an author whose debut novel has been selected by Oprah’s Book Club. But when he returns home to be the best man in his best friend's wedding, the book is passed around their group of friends... and it's revealed Harper had a one-night stand with his best friend's soon-to-be wife. Naturally, drama ensues and Harper is left to try and save his best friend's wedding, all while keeping his eye on his current love interest. It's messy to say the least — but in true rom-com style, ultimately satisfying.
Available to stream on Hulu, iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
10. While You Were Sleeping
This 1995 hit mixes in a bit of soap opera drama — and we’re here for it. Here’s the gist: Lucy (Sandra Bullock) works as a toll collector and is ho-hum lonely until she starts crushing on a handsome commuter. He doesn’t know she exists — that is until she rescues him from being hit by a train after a group of muggers pushes him on the track. As if that’s not enough drama, Lucy’s crush ends up in a coma and, when his family arrives, she’s at his side. They assume she’s his fiance (who they, magically, haven’t met yet) and for whatever reason....she doesn’t correct them. And, yet, there’s one more twist: She falls in love with his brother, Jack, while waiting for him to wake up. *Awkward.*
Available to stream on Hulu, iTunes, Disney+, Amazon Prime Video, Google Play, Vudu, and other streaming services.
11. Romy and Michele’s High School Reunion
As you may have guessed from the title, Romy (Mira Sorvino) and Michele (Lisa Kudrow of Friends fame) are headed to their 10-year reunion to show their “popular” classmates that they’ve achieved success — even concocting a lie about being the inventors of Post-It notes. Spoiler: The people who were picked on in high school end up on top and even taking center stage with an epic interpretive dance to Cyndi Lauper's "Time After Time." Cue the rom-com worthy ending when the once-nerdy Sandy Frink (played by Alan Cumming) who is now handsome and wealthy whisks away Michele — who he's been crushing on since high school — and Romy in his helicopter.
Available to stream on iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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12. You’ve Got Mail
OK, clearly it's a given that Meg Ryan and Tom Hanks are rom-com gold together and this 1998 mashup is no exception. Not only does this movie feature real bookstores (Tom Hanks plays the big bad corporate bookstore owner moving in across the street and threatening to put her independent bookstore out of business) — but it's also a serious throwback to pre-texting days. If you remember the dial-up tone and "You've got mail" greeting, then you will feel serious nostalgia while watching this romance play out.
Available to stream on iTunes, Netflix, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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13. Never Been Kissed
So, if you had a coveted frosted lipstick that you stowed in your Jansport backpack next to your Lisa Frank trapper keeper, then Drew Barrymore's Josie Geller in Never Been Kissed is your girl. Not only is she an undercover reporter posing as a student at her former high school, but she does it with an adult's perspective (something we all wish upon our teenage selves) that gives her the confidence to stick up to the popular clique. Oh, and she also falls in love with her English teacher who doesn't yet know she's not an actual student.... this is a rom-com, after all.
Available to stream on iTunes, Disney+, Amazon Prime Video, Google Play, Vudu, and other streaming services.
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14. As Good As It Gets
If you love an unconventional love story, then As Good As It Gets, is where it's at. Watch as Melvin Udall (Jack Nicholson) — a fiction writer with OCD and a wicked nasty streak — finds love (and a softer attitude) in unexpected ways, including a dog-sitting gig for his neighbor's dog and through the kindness of a waitress (Helen Hunt) who serves him at the local diner. And ohmygod is there anything more rom-com than a line like, "You make me want to be a better man "— let alone hearing it delivered in Nicholson's iconic voice?
Available to stream on Netflix, iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
15. My Best Friend's Wedding
We know, we know — another Julia Roberts movie. But, honestly, what would the '90s be without Roberts and her many contributions to the rom-com genre? My Best Friend's Wedding is special because it shows Roberts in a slightly different role, attempting to ruin the relationship betwen her best friend (Dermot Mulroney) and his soon-to-be wife (Cameron Diaz) just a few days before his wedding. It's hilarious, honest — and proved that sometimes even unhappy endings can still be happy.
Available to stream on Hulu, iTunes, Amazon Prime Video, Google Play, Vudu, and other streaming services.
