The 10 Best Rom-Coms From the Golden Age of Romantic Comedy (1989-1999)
Somewhere around the 2010s, with the rise of streaming, Hollywood suddenly forgot how to make a good rom-com.
There are still the occasional outliers (think movies like Crazy, Stupid, Love, Crazy Rich Asians, and Rye Lane), but we are now in such a rom-com crisis that movies like How to Lose a Guy in 10 Days are being re-evaluated as modern classics. That movie has some charms, but it couldn’t hold a candle to the kind of stuff being produced in Hollywood and the UK in the 1990s — of which we have listed 10 of the best below.
One thing to note: for inclusion on this list, the movie needs to really feel like a rom-com — as in, the romance should always eventually outweigh the comedy. This means, respectfully, there is no room for otherwise excellent flicks like There’s Something About Mary or The Wedding Singer. We also — again, with respect — cannot include teen movies like Clueless or 10 Things I Hate About You. Luckily, there are so many great movies from that awesome decade for cinema that it really doesn’t matter.
It’s fitting that the movie that comes first on this list is also widely considered to be the greatest romantic comedy of all time. Directed by the late, great Rob Reiner, When Harry Met Sally has everything you could possibly want from this kind of movie — cozy knitwear, tasteful apartments, New York in Autumn, an enemies to lovers arc, a New Year’s Eve countdown and kiss, Meg Ryan…
What can we say? If you enjoy seasonal romances that take place in that city (think Serendipity, The Devil Wears Prada), this is basically the perfect movie. And yes, we’ll have what she’s having.
A year after Harry (spoiler) met Sally, much of the world met Julia Roberts (the most featured star on this list) for the first time in Garry Marshall’s Pretty Woman, a movie that turned its $17 million budget into half a billion at the box-office — solidifying the rom-com’s place as one of Hollywood’s biggest earners at that time.
Some parts of the movie — which tells the story of a sex worker who falls in love with a wealthy client (and vice versa) — probably haven’t aged the best, but the chemistry between Roberts and Richard Gere is still undeniable. Check this one out if you liked Gere in An Officer and a Gentleman.
The second Meg Ryan movie on this list is called Sleepless in Seattle and it’s the story of a widower and father (played by Tom Hanks) who thinks he might have met the next great love of his life after his son convinces him to spill his heart out on a radio show.
This is a great one to watch if you liked When Harry Met Sally or if you appreciate that era of Hanks — especially movies like Big, or the Meg Ryan-starring Joe Versus the Volcano.
After Meg Ryan and Julia Roberts, Hugh Grant was probably the third great star of the rom-com golden age — and he rarely gave a better performance than the one he gave in the Richard Curtis-scripted classic, Four Weddings and a Funeral.
The Oscar-nominated film basically helped to invent the British rom-com as a subgenre, as well as establishing Curtis’ style and setting up his career. If you like his later films (like Yesterday and Love Actually), this is one you’ll want to see.
Another ‘90s breakout who only later became a mainstay of the rom-com genre (think movies like The Proposal and Two Weeks Notice) is Sandra Bullock. The future Oscar winner got her breakout role in 1995’s While You Were Sleeping, a story about a New York subway ticket kiosk worker who pretends to be the fiancee of a man who falls into a coma after falling on the tracks.
In classic rom-com fashion, the sleeping man (played by Peter Gallagher) is the one she originally dreams of marrying, but it’s his brother (Bill Pullman, pre-Independence Day) who she soon falls in love with.
The second Julia Robert film on our list of ‘90s rom-coms is the 1997 classic My Best Friend’s Wedding. This is the one where Roberts plays the titular friend-zoned pal of Dermot Mulroney’s groom-to-be. Rounding out the film’s attractive love triangle is Cameron Diaz, who plays Mulroney’s aggressively perfect fiance.
If you love that era of Diaz (think The Mask, There’s Something About Mary), this is one you’ll want to see for sure.
Shakespeare in Love is probably best known these days as the film that denied Saving Private Ryan the Best Picture award at the Oscars — but don’t let that get in the way of how enjoyable it is. This is the movie where Joseph Fiennes plays William Shakespeare and Gweneth Paltrow plays his actress and love interest, Viola de Lesseps.
Written by the great Tom Stoppard and featuring an all-star cast that includes Judy Dench and Geoffrey Rush, this is the ideal film to put on if you haven’t stopped crying since Hamnet.
1998’s You’ve Got Mail isn’t just the third Meg Ryan movie on our list, it’s also the second — after Sleepless in Seattle — that’s directed by Nora Ephron and the second to feature both her and Tom Hanks. If it ain’t broke, etc…
The movie was essentially a modern update of the Jimmy Stewart classic, The Shop Around the Corner — so if you’re a fan of that one or appreciate romantic movies set in the literary world, this is one you have to see.
And speaking of romantic movies set in the literary world, Notting Hill, released a year after You’ve Got Mail, created such a character of the travel book store in which its set that fans of the film still flock to that London location to this day.
This was the movie that reunited Hugh Grant and Richard Curtis while also bridging the Atlantic rom-com divide by getting Julia “queen of the ‘90s” Roberts involved, too. If you’re a fan of Curtis or even the Bridget Jones movies, I guarantee you’ll like it. It might be the best rom-com ever made.
We might not end this list with the best movie, but Runaway Bride did manage to reunite the stars of Pretty Woman — Richard Gere and you know who — nine years after that enormously successful movie. So, in a way, it feels like a nice way to bookend this piece.
The story follows Roberts’ Maggie Carpenter, a romantic so flaky that she’s already left three men at the altar by the time Richard Gere’s reporter arrives in town to write a story about her. I bet you can’t guess what happens next.
