You’ve Got Love! Fresh From An Era Of Teen-Angst Dramedies, The ’90s Were A Rom-Com Fan’s Dream

Pretty Woman, You've Got Mail, While You Were Sleeping movie collage
Everett Collection

Romantics will never forget the scene that introduced the world to the uber rich, strikingly handsome Edward Lewis (played by Richard Gere), when he impatiently borrows his accountant’s Lotus Esprit and rips it around town only to get lost deep into Hollywood. When Edward observes a group of prostitutes who could possibly offer him directions, he pulls the Lotus Esprit over and rolls down his window, asking the quirkiest of the bunch: “What’s your name?” 

“What do you want it to be?” — responds Vivian Ward (Julia Roberts). That instantaneous, delicious magic between the two made Pretty Woman one of the most iconic rom-coms of the decade, and set in motion a steady parade of movies that would melt our hearts and leave us wanting more. 

The ’80s indulged our unresolved high school vulnerabilities via quirky teens figuring out their lot and their love lives in a single swoop. By the time the ’90s rolled around, though, onscreen love and laughter was doled out mostly by grownups who seemed a bit more like us, working everyday jobs and screwing up, then resurrecting, their romances, well, in ways that were still more Hollywood magic than our own weary reconciliations. In short: the beating heart of a rom-com’s magic.

Pretty Woman, Richard Gere, Julia Roberts, 1990

Everett Collection

In the process, breakout stars who are now A-listers and power pairings emerged: Julia Roberts and Richard Gere (who bookended the decade with rom-com smashes), Tom Hanks and Meg Ryan, Cameron Diaz, Sandra Bullock, Hugh Grant, Renée Zellweger. And the list goes on. 

The decade launched with the first of the Roberts-Gere pairings, in a film that has become the stuff of rom-com legend. Making the most of Roberts’ stellar comic chops and leggy, coltish beauty paired with Gere’s upper-crust looks and polished savoir-faire, Garry Marshall’s Pretty Woman told the tale of Vivian Ward, a hooker with a heart of gold and gobs of street smarts, and repressed businessman Edward Lewis, who sees a diamond in the rough in his paid companion.  

There may never be a better final line, rom-com or otherwise, than Roberts’ empowered spin of her character’s fairy tale ending, when she responds to Gere’s question “So what happens after he climbs up and rescues her?” with “She rescues him right back!” The film earned the fledgling star a Golden Globe and an Oscar nomination, cementing her status as a sought-after actor.

My Best Friend's Wedding, Cameron Diaz, Dermot Mulroney, 1997,

TriStar/Courtesy Everett Collection

Seven years later, Roberts scored another Golden Globe nomination for My Best Friend’s Wedding, playing lovelorn food critic Jules, whose semi-serious plan to wed her ex-turned-bestie Michael (Dermot Mulroney) if neither found love by their 28th year, is thwarted by wealthy, winsome Kimmy (a charming Cameron Diaz, ditching her trademark ditz to great effect). As a young woman working through a simultaneous broken heart and bruised ego on the way to emotional maturity, Roberts reinforced her blossoming A-list cred.

Julia, Julia & More Julia 

In 1999, Marshall reunited Roberts and Gere (plus their Pretty Woman costar Hector Elizondo) in Runaway Bride. Roberts plays the not-quite-married Maggie who finds love with New York columnist Ike after he tracks her down while righting wrongs in the snarky piece he wrote about her. Though it failed to capture the magic of Pretty Woman, Runaway was a still a runaway hit at the box office.

Meanwhile, another soon-to-be Roberts costar launched lasting fame, this time from the other side of the pond. 

Four Weddings and a Funeral, Hugh Grant, Andie MacDowell, 1994,

Gramercy Pictures/courtesy Everett collection

Rare was the female moviegoer who, having purchased a ticket to 1994’s Four Weddings and a Funeral, didn’t fall for Hugh Grant’s charmingly rumpled Brit commitment-phobe Charles, who changes his mind something fierce when ballsy, beautiful American Carrie (Andie MacDowell) sashays into his life. And then out. And then in. Again and again and again. Bolstered by a stellar cast of wry comic talent, the scrappy, low-budget production stood out among its cookie-cutter rom-com brethren, becoming an Oscar nominee, awards-season favorite and timeless rom-com hit.

Five years later, Four Weddings screenwriter Richard Curtis returned with Notting Hill (1999). Hugh Grant charmed once again as bumbly English bookstore owner William Thacker, who encounters Julia Robert’s mega-movie-star Anna Scott when she wanders into his London shop. Longing for more than the glitz and artifice of Tinseltown, Anna falls for William until a series of unfortunate events sparks her apprehension and drives the pair apart. In true Hollywood fashion, Thacker is ultimately just a workaday boy standing in front of a really famous girl and asking her to love him once again. 

Grant and Roberts each received a Golden Globe nomination for their work, and the film boasted the biggest opening for a romantic comedy ever, besting Roberts’ Best Friend’s Wedding, but soon ceding that record to her Runway Bride.

A New Romantic Pairing 

You've Got Mail, Tom Hanks, Meg Ryan, 1998,

Warner Brothers/courtesy Everett Collection

At the same time, another superstar comic pairing, Tom Hanks and Meg Ryan, was winning over moviegoers with the help of journalist and screenwriter Nora Ephron.

In 1993’s Sleepless in Seattle, Ephron — whose 1989 rom-com When Harry Met Sally… also starred Ryan and paved a path for the ’90s romantic-comedy sensibility — unites lovely Baltimore journalist Annie and lonesome widower and single dad Sam, a Seattle transplant, via Sam’s rending story of love and loss shared over a call-in radio show. In this modern era of dating apps, photo-filters and speedy matchmaking apps, watching Sam and Annie’s slow, steady and blessedly lust-free march to an iconic scene atop the Empire State Building is cinematic heaven for true romance lovers.

Five years later, the pair returned (this time a bit more tech savvy) in Ephron’s You’ve Got Mail. This time they play warring book peddlers — Hanks shrewd and corporate and Ryan cozy and kid-centric. Their old-fashioned, conversation-driven love exchange cultivated in the anonymity of an AOL chat room made the film as unforgettable as that piercing AOL dial-up tone and “You’ve got mail!” announcement.

Happily Ever After 

HOPE FLOATS, Harry Connick Jr., Sandra Bullock, 1998, carrying" (image upgraded to 17.7" x 11.9")

20th Century Fox Film Corp./Courtesy: Everett Collection

As Roberts and Ryan were becoming silver-screen rom-com queens, another comely cutie was parlaying the genre into a multifaceted (and multimillion-dollar) career. Virginia-born and internationally raised, Sandra Bullock amassed a resumé of charming rom-coms — Love Potion No. 9, The Thing Called Love, Hope Floats — in rapid succession. But, having shown flickers of comic savvy in her star-making turn in the ’94 thriller Speed, 1995’s While You Were Sleeping sealed the deal. Bullock played Lucy, a Chicago toll collector who springs into action to save her secret crush from being smooshed by a train, setting in motion a series of white-lies-meets-true-love events that make her a part of his family for real.

Jerry Maguire, Tom Cruise, Renee Zellweger, 1996.

TriStar Pictures/courtesy Everett Collection

Family for real is also at the heart of Cameron Crowe’s 1996 award-magnet Jerry Maguire, a formidable building block in Tom Cruise’s burgeoning leading-man empire. The film was America’s true introduction to Renée Zellweger, who delivered a winning, sweet and spunky performance as single mom Dorothy Boyd, who refuses to let Cruise’s titular slick sports agent fall victim to his money-hungry lesser angels. She firmly coaches him to the conclusion that love, friendship and family are the ultimate winning team. 

Every romantic comedy of the ’90s took us to the same place, and it’s why we love them all.

February 2021
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February 2021

1990s Rom-Coms

Pop some popcorn and cozy up to feel-good movies and TV shows from a generation ago.

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