It's all been downhill from there.
The 8 Best '90s Rom-Coms That Prove The Genre Will Never Be That Good Again

Chloe Williams serves as B+C’s Entertainment Editor and resident Taylor Swift expert. Whether she’s writing a movie review or interviewing the stars of the latest hit show, Chloe loves exploring why stories inspire us. You can see her work published in BuzzFeed, Coastal Review, and North Beach Sun. When she’s not writing, Chloe’s probably watching a Marvel movie with a cherry coke or texting her sister about the latest celebrity news. Say hi at @thechloewilliams on Insta and @popculturechlo on Twitter!
There's nothing like a good rom-com, and unfortunately there's also nothing like a bad rom-com. With dull scripts and (at times) even duller characters, the romance movie market has been flailing for me in recent years. I'm really hoping movies like Anyone But You, Set It Up, and Materialists revive the era of the rom-com (recession core!!!) but I still stand by the fact the 1990s and early 2000s is the best rom-com era of all time. Here are 8 movies to prove it.
Keep reading for the 8 best '90s rom-coms that put the rest to shame.
1. Notting Hill (1999)
Universal Pictures
Notting Hill follows famous American actress Anna (Julia Roberts) who stumbles into Will's (Hugh Grant) Notting Hill bookstore...and his life. But Anna's fame (and the paparazzi) make everything more complicated.
Notting Hill stars Hugh Grant, Julia Roberts, Rhys Ifans, and James Dreyfus.
2. While You Were Sleeping (1995)
Hollywood Pictures
This '90s rom-com follows Sandra Bullock's character Lucy, who works as a Chicago Transit Authority ticket booth operator. And her life gets more exciting than she could have predicted when she rescues her longtime crush from an oncoming train...and his family believes they're engaged.
While You Were Sleeping stars Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle, Glynis Johns, and Jack Warden.
3. You've Got Mail (1998)
Warner Bros. Pictures
When Harry Met Sally might be Meg Ryan's most iconic movie, but You've Got Mail is arguably the most romantic. The movie follows two rival bookstore owners (Meg Ryan and Tom Hanks) who don't realize they've been falling for each other over email.
You've Got Mail stars Meg Ryan and Tom Hanks.
4. Sleepless In Seattle (1993)
TriStar Pictures
Tom Hanks and Meg Ryan also starred together in Sleepless In Seattle, in which widower Sam's (Tom Hanks) son calls into a radio show to find Sam a partner — and Annie (Meg Ryan) decides to find him IRL.
Sleepless in Seattle stars Meg Ryan, Tom Hanks, and Bill Pullman.
5. Much Ado About Nothing (1993)
Renaissance Films
Yes, this '90s rom-com is actually a Shakespearean tale. Much Ado About Nothing follows Hero and Claudio who decide to set the very-single and very argumentative Benedick and Beatrice up with each other. Fun fact, this loosely inspired Anyone But You!
Much Ado About Nothing stars Emma Thompson, Kenneth Branagh, Michael Keaton, Robert Sean Leonard, Keanu Reeves, Emma Thompson, Denzel Washington, and Kate Beckinsale.
6. Shakespeare In Love (1998)
Universal Pictures/Miramax
And I can't talk about Shakespeare adaptations without mentioning Shakespeare In Love! The movie follows the one and only William Shakespeare (Joseph Fiennes), who totally runs out of money and inspiration...until he meets Viola De Lesseps (Gwyneth Paltrow).
Shakespeare In Love stars Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Colin Firth, Ben Affleck, Judi Dench, Simon Callow, Jim Carter, Martin Clunes, Antony Sher, and Imelda Staunton.
7. Pretty Woman (1990)
Touchstone Pictures
Pretty Woman is the perfect mix of '80s and '90s, and the fact that Julia Roberts stars as the titular pretty woman makes this movie a must-watch. Vivian Ward (Julia Roberts) is a Hollywood escort who's hired by wealthy Edward Lewis (Richard Gere) to accompany him over the course of a week. And, of course, their business deal quickly turns into something more.
Pretty Woman stars Julia Roberts, Richard Gere, Jason Alexander, and Héctor Elizondo.
8. Four Weddings and a Funeral (1994)
Rank Film Distributors
This '90s rom-com follows bachelor Charles (Hugh Grant), who — over the course of four weddings and a single funeral — realizes he's fallen in love with Carrie (Andie MacDowell).
Four Weddings and a Funeral stars Hugh Grant, Andie MacDowell, Kristin Scott Thomas, Simon Callow, James Fleet, John Hannah, Charlotte Coleman, David Bower, Corin Redgrave, and Rowan Atkinson.
Read 10 Cringy 90s Movies That Would Never Be Made Today for more throwbacks!