Who doesn’t love a good romantic comedy from the ’90s? From Clueless to Pretty Woman, the 1990s delivered more iconic rom-coms (or chick flicks, if you must) than any other decade.
There’s a reason we keep coming back to the decade when romantic comedies reigned supreme, and stars like Julia Roberts and Meg Ryan captured America’s hearts.
’90s rom coms pull at our heartstrings and poke at our funny bones with their meet-cutes, sexy complications, grand over-the-top gestures, and, of course, their happy endings. And they’re probably to blame for our wildly inflated romantic and relationship expectations. Is it too much to ask for a confession in the rain?
Thanks to Netflix, we’re in the midst of a rom-com revival of sorts, but they just don’t make ’em like they used to. It all came to an end on December eve in 1999. Just kidding. Well, sort of, because the early 2000s marked their decline. Studio executives and A-listers have long moved on from lighthearted romance to epic fantasy franchises and cinematic universes.
But we’ll always have the era of rom-com gold.
So, whether you’re planning a date night, a girls’ night, or a nostalgic night in with a movie that feels like a warm blanket, you’ve come to the right place. I dusted off my VHS tapes and compiled a list of the best romantic comedies from the ’90s guaranteed to hit you right in the feels. Happy viewing!
And if you’re still on a nostalgia kick after that, check out our list of the best romantic comedies from the 80s too!
10 BEST ROMANTIC COMEDIES OF THE 90s
10. Shakespeare In Love (1998)
Miramax Films
Watch on: Hulu, Prime Video, Vudu
IMBD: 7,1
Cast: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush
Director: John Madden
What’s it about?
The 1998 Oscar-winning film imagines a young William Shakespeare (Fiennes) who suffers from writer’s block and falls in love with Viola (Paltrow), who eventually helps him overcome it. The film follows the Bard as he writes Romeo and Juliet, the greatest love story ever told, with Viola as his inspiration.
What makes it work?
Shakespeare In Love is set in the glory days of Elizabethan theatre, and if it lacks historical accuracy, it makes up for it in romance. As an added bonus, you get to enjoy the film’s wonderful theatrical backdrop, gorgeous costumes, colorful characters, witty dialogue, and a wealth of Willie S. quotes.
Memorable quote: “Love knows nothing of rank or river bank.”
9. While You Were Sleeping (1995)
Buena Vista Pictures
Available on: Prime Video, Vudu
IMBD: 6,7
Cast: Sandra Bullock, Bill Pullman, Peter Gallagher
Director: Jon Turteltaub
What’s it about?
Lucy Eleanor Moderatz (Bullock), a lonely Chicago transit worker, heroically saves her crush, business commuter Peter Callaghan (Gallagher), from an approaching train. Peter ends up in a coma, and his family mistakenly believes Lucy is his fiancee. Before she has a chance to correct them, the Callaghans warmly embrace her as one of their own. Things become further complicated when she falls for Peter’s brother, Jack (Pullman).
What makes it work?
The 1995 mistaken-identity rom-com is all heart: romance, family focus, a Christmas feel, and that Sandra Bullock charm. While You Were Sleeping is a story about love, but it’s also about loneliness. Lucy is a lovable underdog who pretends to be Peter’s fiancee not because she wants to marry him but because she has no family. She’ll sneak up on you before you know it, and you’ll find yourself rooting for her happily ever after in this terribly underappreciated ’90s romantic comedy.
Memorable quote: “I’ve had a really lousy Christmas, you’ve just managed to kill my New Year’s. If you come back on Easter, you can burn down my apartment.”
8. Jerry Maguire (1996)
Sony Pictures
Available on: Netflix, Prime Video, Vudu
IMBD: 7,3
Cast: Tom Cruise, Renée Zellweger, Cuba Gooding Jr.
Director: Cameron Crowe
What’s it about?
Jerry Maguire (Cruise) is a slick sports agent who grows a conscience, which gets him fired from his job. Only two people support him as he starts his own business and tries to rebuild his life: his sole client, a second-rate football player Rod Tidwell (Gooding Jr.), and his former co-worker Dorothy Boyd (Zellweger), a single mom with a massive crush on both Jerry and his zeal for life.
What makes it work?
One of the best romantic comedies of the 90s follows Jerry’s career and his romance with Dorothy, seamlessly blending the sports and rom-com genres. In the 1996 classic, Jerry and his friends are on a quest for redemption, and watching them take a leap of faith and end up in a better place is nothing short of inspiring. And watching Jerry and Dorothy fall in love while trying to keep a struggling business afloat is pure movie magic that will instantly fix your bad day.
Memorable quotes: “Show me the money”, “You had me at hello”, “You complete me”.
7. There’s Something About Mary (1998)
20th Century Fox
Available on: Prime Video, Netflix, Vudu
IMBD: 7,1
Cast: Cameron Diaz, Matt Dillon, Ben Stiller
Directors: Bobby and Peter Farrelly
What’s it about?
It’s been 13 years since an embarrassing freak accident ruined Ted’s (Stiller) dream prom date with Mary (Diaz). Ted is still fond of her and needs closure, so he employs a sleazy private investigator, Pat Healy (Dillon), to track her down. Healy does the job but falls for Mary himself and does everything to keep Ted away from her. On the other hand, Ted makes his way back into Mary’s life and attempts to win her over, competing with Healy and a slew of other psychotic suitors.
What makes it work?
You should probably avoid the 1998 crude rom-com if you don’t have a high tolerance for low humor. After all, There’s Something About Mary is a love story made by the Farrelly brothers, the same guys who gave us Dumb and Dumber. Everyone else, however, will crumple with laughter and enjoy this naughty and politically incorrect story about a geek who gets the girl of his dreams. The unusually guy-friendly rom-com is equal parts sweet, funny, and gross, and you’ll never look at hair gel the same way again after watching it.
Memorable quotes: “Is that… Hair gel?”, “I couldn’t believe that she knew my name. Some of my best friends didn’t know my name”.
6. Sleepless in Seattle (1993)
TriStar Pictures
Available on: Netflix, Prime Video, Vudu
IMBD: 6,8
Cast: Tom Hanks, Meg Ryan, Bill Pullman
Director: Nora Ephron
What’s it about?
On Christmas Eve, 8-year-old Jonah calls into a Seattle radio talk show, concerned about his sad and still single dad, Sam Baldwin (Hanks). He convinces his father to talk on air, and the recent widower, Sam, ends up pouring his heart out. One of the listeners is a newspaper reporter, Annie Reed (Ryan), who, despite being engaged herself, becomes increasingly interested in Sam. So she wastes no time and does some pre-Google sleuthing to find him and try to make a connection of her own.
What makes it work?
The central couple in the 1993 rom-com barely shares any screen time, meeting for the first time at the end of the film. But Nora Ephron’s gimmick works beautifully in Sleepless in Seattle; you’ll be so invested in the idea of Annie and Sam meeting on the top of the Empire State Building because they’re MFEO. Throw in some clever humor and a nostalgic soundtrack, and you’ve got yourself a perfect Friday night (re)watch!
Memorable quote: “Destiny is something we’ve invented because we can’t stand the fact that everything that happens is accidental.”
5. She’s All That (1999)
Miramax Films
Available on: Netflix, Prime Video, Vudu
IMBD: 5,9
Cast: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard
Director: Robert Iscove
What’s it about?
When his queen-bee girlfriend dumps him, the high school golden boy Zack Siler (Prinze Jr.) goes through a full-fledged identity crisis. To shield his pride, Zach makes a bet with his friends that he can transform any girl into a prom queen, and the chosen one is Laney Boggs (Cook), a high school outcast and art-loving geek. But what Zack did not bet on was falling in love with her.
What makes it work?
The 1999 adaptation of Pygmalion is a delightful coming-of-age classic. The delightful 90’s cast, the iconic makeover (remove the glasses and bam – you’re done), laugh-out-loud scenes, and the most random choreographed dance sequence ever are all part of She’s All That’s lasting appeal. But the best part of the charming teen rom-com is watching Zack and Laney grow beyond the high-school stereotypes as they try to figure out love for the first time.
Memorable quotes: “Sometimes when you open up to people, you let the bad in with the good”, “I feel just like Julia Roberts in Pretty Woman. You know, except for the whole hooker thing”.
4. Four Weddings and a Funeral (1994)
Rank Film Distributors
Available on: Prime Video, Vudu
IMBD: 7,1
Cast: Hugh Grant, Andie MacDowell, James Fleet
Director: Mike Newell
What’s it about?
Charles (Grant), an English bachelor, and his eccentric friends appear to be unlucky in love. However, Charles is smitten when he meets American beauty Carrie (MacDowell) at a wedding and believes his luck has changed. As their paths continue to cross – over four weddings and one funeral – he comes to believe they belong together, even if their timing is always off.
What makes it work?
One of the best British romantic comedies of all time takes place almost entirely at the titular ceremonial occasions. This provides a gorgeous backdrop for Charles and Carrie’s love story (well, except the funeral), with old country estates, lovely hats, and cheerful-looking Brits. The heart-warming story, romantic shenanigans, zippy dialogue, and Hugh Grant at his best are sure to bring a smile to your face, no matter how many times you see it.
Memorable quotes: “There I was, standing there in the church, and for the first time in my whole life I realized I totally and utterly loved one person. And it wasn’t the person next to me in the veil. It’s the person standing opposite me now… in the rain”, “Is it still raining? I hadn’t noticed”.
3. Clueless (1995)
Paramount Pictures
Available on: Netflix, Prime Video, Vudu
IMBD: 6,8
Cast: Alicia Silverstone, Brittany Murphy, Paul Rudd
Director: Amy Heckerling
What’s it about?
Cher Horowitz (Silverstone) is the most popular girl at her Beverly Hills high school. When the new student, Tai (Murphy), suddenly becomes more popular than her, Cher begins to develop a new perspective on life while simultaneously falling for her ex-stepbrother, Josh (Rudd).
What makes it work?
Based on Jane Austen’s Emma, this 1995 teen comedy is a classic and a pop culture phenomenon for a reason. Clueless not only ensures Cher meets the Baldwin of her dreams, but also focuses on her friendships and personal growth. And did I mention the clothes? And the quotes? As if any list of the best romantic comedies of the 90s would be complete without this endlessly rewatchable gem.
Memorable quotes: Ah, there’s just too many! But let’s stick with two for the sake of keeping this list reasonably short: “Cher’s saving herself for Luke Perry”, “You’re a virgin who can’t drive”.
2. 10 Things I Hate About You (1999)
Buena Vista Pictures
Available on: Prime Video, Vudu
IMBD: 7,3
Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
Director: Gil Junger
What’s it about?
The popular and pretty Bianca Stratford wants to date boys, but her overbearing father won’t let her until her rebellious sister Kat (Stiles) does the same. The only issue? Kat would rather die than go out with a boy. Bianca’s potential boyfriend desperately tries to set Kat up with Patrick Verona (Ledger), another rebel who may just be able to find his way into Kat’s heart.
What makes it work?
The 1999 riff on Shakespeare’s The Taming of the Shrew is one of those rare films in which everything just works. The incredible cast, killer soundtrack, feminist discussions, love story, and pitch-perfect comedy remain fresh and sharp even two decades later. And the two most memorable scenes in 10 Things I Hate About You, Patrick crashing Kat’s soccer practice and singing Can’t Take My Eyes Off You and Kat reciting THE POEM, still make our hearts flutter.
Memorable quotes: “But mostly I hate the way I don’t hate you. Not even close, not even a little bit, not even at all.”
1. Pretty Woman (1990)
Buena Vista Pictures
Available on: Prime Video, Vudu
IMBD: 7
Cast: Richard Gere, Julia Roberts, Jason Alexander
Director: Garry Marshall
What’s it about?
A billionaire businessman, Edward Lewis (Gere), hires a sex worker, Vivian Ward (Roberts), to play the role of his girlfriend and accompany him to a few social events. Trouble arises when the two catch feelings for each other and must now bridge the gap between their two worlds.
What makes it work?
A 1990 take on the Cinderella story, Pretty Woman, is so ingrained in our cultural understanding of rom-coms that we can’t imagine a world without it. I mean, where do I even start? The unforgettable theme song? The sizzling chemistry between the leads? Scads of laughs and memorable scenes? Pretty Woman has it all, including a fairytale ending for our rom-com queen, Julia Roberts. The best romantic comedy of the 90s is due for a rewatch this weekend. Otherwise, you’d be making a big mistake. Big. Huge.
Memorable quote: “She rescues him right back.”
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