Some completely missed the mark
This rom-com famously used AOL email accounts to drive the now-implausible love plot between Ryan and Hanks' characters. Even with technology evolving, this on-screen affair remains timeless.
Combine two charismatic talents with a sharp script, and you get magic. This film keeps its leads separate most of the time, but when they meet, it's obviously at the top of the Empire State Building. No wonder these two kept getting on-screen together!
An old unrequited high school crush inspires Ted (Ben Stiller) to hire a private investigator who ends up trying to win Mary over for himself. The film is daringly funny, like when Mary uses a special kind of 'hair gel.'
Matthew Broderick and Meg Ryan costar as strangers who team up after they discover their exes are dating each other. There's nothing like a little meddling to stir the romance.
The fashion moments in this movie are iconic, and it puts a hilarious spin on a Jane Austen classic.
Meg Ryan's humor really shines in this role as a woman who flies to France to confront her straying fiancé. She gets mixed up with a charming crook in front of gorgeous French backdrops.
This film starring Freddie Prinze Jr. and Rachael Leigh Cook is the epitome of a '90s classic, featuring the transformation of a girl from 'unattractive' to prom queen by simply taking off her glasses!
Though it is a teen sex comedy following four high school friends determined to have sex before they graduate, it still has a heart of gold and gives the romantic interests goals of their own, so the girls aren't solely there for the boys.
Julia Roberts and Dermot Mulroney star at the height of their appeal in this hilarious film, which was a surprising example that even unhappy endings can be happy.
Probably one of the strangest premises for a rom-com, a woman rescues a man from a train incident, and while he's comatose she lies to his family about being his fiancée, then falls in love with his brother. It's all in Sandra Bullock's acting.
Though Andie MacDowell is in the film, it really just stars Hugh Grant, his good-natured wit, and his floppy hair.
While this movie might not hold up as well in this day and age, Julia Roberts's megawatt energy makes it an eternal classic.
See also: Favorite films of the past that have not aged well.
Jennifer Aniston shines in this underrated rom-com about a career-obsessed woman who hires a man (Jay Mohr) to pretend to be her fiancé. It's unexpectedly forward-thinking!
Angela Bassett plays a busy executive and single mom who takes a much-deserved Caribbean vacation at the request of her friend, and meets the steamy, young Taye Diggs. Sexy and subversive, this film is the rom-com for the modern woman, passing the Bechdel test with ease.
One of Wes Anderson's most stylish films stars Jason Schwartzman as an extracurricular-motivated student who competes with a local industrialist, played by Bill Murray, for the affections of a widowed teacher. It hilariously encapsulates what it's like to have a crush.
A big American star and a doesn't-know-he's-handsome bookshop owner strike up a memorable romance. "I'm just a girl, standing in front of a boy, asking him to love her"—need we say more?
Drew Barrymore's goofy charm and big heart as an undercover reporter posing as a student at her former high school will win you over, especially as she falls in love with her English teacher.
Julia Roberts and Richard Gere reunited for this film about a woman who has left three grooms at the altar and the jaded, divorced reporter doing a story on her.
This light-hearted adaptation of William Shakespeare's 'Taming of the Shrew' stars Julia Stiles and the late Heath Ledger, and there's never a dry eye when she reads him that iconic final poem.
Set in the '80s, Adam Sandler plays an endearing wedding singer recently left at the altar, who helps Drew Barrymore's character plan her wedding to the wrong man. The actors' chemistry is unparalleled!
John Cusack and Minnie Driver star in this film about a professional assassin who accepts an assignment in the same town where he is to attend his 10-year high school reunion.
From the popular girl to the artsy guy, from the wannabe rapper to the football jock, this rom-com gives you all the high school tropes, so you already know the not-so-popular guy gets the girl of his dreams.
Taye Diggs plays an author whose novel has been selected by Oprah's Book Club, and a best man to his best friend's wedding. Problems arise when people read the book and find out he slept with the soon-to-be wife.
Melissa Joan Hart and Adrian Grenier star in this high school romance where the cool girl needs a prom date and settles for her decidedly uncool neighbor. But what happens when the popularity gets to his head?
Jack Nicholson plays a nasty old writer with OCD who finds love and becomes a better man in unexpected ways, from dog-sitting for his neighbor to a kind waitress (Helen Hunt) at the local diner.
Ben Stiller's directorial debut was a cult hit and remains a gem of the '90s. Winona Ryder plays an aspiring documentarian, Ethan Hawke is in full charismatic force, and everyone's just trying to figure out who they are and what they want in life.
Bill Murray's cynical Pittsburgh weatherman is sent to Punxsutawney, Pennsylvania, with his producer, played by Andie MacDowell, on what turns out to be quite a literal dead-end assignment.
In this underrated rom-com, George Clooney and Michelle Pfeiffer play out a grown-up love story between busy single working parents who are brought together by a missed field trip.
No matter what kind of mood you’re in, you can always rely on a classic '90s romantic comedy for an instant boost. A mixture of nostalgia, style inspiration, giggles, and tears, these iconic films are the perfect escape from the tech-heavy romance of 2020, returning to a time before dating apps and read receipts.
Click through to see the greatest and most rewatchable rom-coms of the beloved decade, featuring all the floppy hair, high-waisted jeans, wit, and charm you’ll ever need.
The most essential rom-coms of the '90s
Here's what to watch on a cozy night in
MOVIES What to watch
No matter what kind of mood you’re in, you can always rely on a classic '90s romantic comedy for an instant boost. A mixture of nostalgia, style inspiration, giggles, and tears, these iconic films are the perfect escape from the tech-heavy romance of 2020, returning to a time before dating apps and read receipts.
Click through to see the greatest and most rewatchable rom-coms of the beloved decade, featuring all the floppy hair, high-waisted jeans, wit, and charm you’ll ever need.