The 20 Best '90s Romantic Comedies Ranked

Maybe there's a certain amount of recency bias at play, but the 1990s feel like a modern golden age for romantic comedies. You have icons of the genre (Tom Hanks, Meg Ryan, Sandra Bullock, Julia Roberts — the list goes on and on) being paid more than ever before to keep churning out delightful little films throughout the entire decade. It almost doesn't matter if the stories are original or thought-provoking, because the stars are so charming that you simply won't care if you're being challenged intellectually. The 1990s also represent a welcome shift in Hollywood's approach to the genre, in terms of telling stories that aren't... The post The 20 Best '90s Romantic Comedies Ranked appeared first on /Film.

The 20 Best '90s Romantic Comedies Ranked

Maybe there's a certain amount of recency bias at play, but the 1990s feel like a modern golden age for romantic comedies. You have icons of the genre (Tom Hanks, Meg Ryan, Sandra Bullock, Julia Roberts — the list goes on and on) being paid more than ever before to keep churning out delightful little films throughout the entire decade. It almost doesn't matter if the stories are original or thought-provoking, because the stars are so charming that you simply won't care if you're being challenged intellectually.

The 1990s also represent a welcome shift in Hollywood's approach to the genre, in terms of telling stories that aren't always centered on straight white Americans. We begin to see romantic comedies that feature leads who look different from the ones who had played prominent roles on the big screen before, leading to entirely different perspectives. These films would pave the way for a much more diverse landscape for romantic comedies in the decades to come.

Pretty Woman

During the peak of her romantic comedy career, Julia Roberts generally cultivated a girl-next-door persona, one that was intrinsically challenged by her work in "Pretty Woman." Here, she plays Vivian, a Los Angeles prostitute who falls in love with a rich corporate executive (Richard Gere), a role not exactly in line with the other big films she had made up to this point. "Pretty Woman" has almost every romantic comedy trope in the book: the hooker with a heart of gold, the fake relationship that slowly becomes real, the icy businessman who is changed for the better by love. It's the whole nine yards.

But if there's one thing that elevates "Pretty Woman" above the fray, it's the classic scene where Vivian attempts to go shopping on Rodeo Drive. The sales associates won't give her the time of day, believing that she can't afford anything in the store and shooing her away. This sets a post-makeover Vivian up for the ultimate fist-pump moment, when she goes back to the store and turns the tables on the employees, showing them just how much money they lost out on in commissions for refusing her sale. Truly the revenge that we've all dreamed of at one point or another.

Love Potion No. 9

When two reserved, bashful scientists find themselves in position of a chemical compound that makes them immediately desirable to the opposite sex, things are bound to get a little out of control. "Love Potion No. 9" is an underrated romantic comedy from the early 1990s that stars Sandra Bullock and Tate Donovan as two undeniably attractive people desperately trying to suppress their natural charms until they're finally allowed to unleash them later in the film. (Honestly, it's almost impressive how many times in Sandra Bullock's career she's been cast as the awkward weirdo with no sex appeal -- someone needs to speak to her agent!)

"Love Potion No. 9" may not be the romantic comedy that most people associate with the 1990s, but it's arguably one of the most endearing, if only for the off-the-charts chemistry between Donovan and Bullock. Their on-screen romance would echo into real life, as well: The couple dated for four years in the early 1990s, beginning on the set of "Love Potion No. 9."

The Wedding Singer

Adam Sandler was prolific throughout the late 1990s, putting out a number of goofy comedies over the course of just a few years. "The Wedding Singer" is him at his least over-the-top, and he somehow manages to overcome his natural class clown instincts in service of a genuinely adorable romantic comedy. Sandler stars as Robbie Hart, a blissfully in-love wedding singer whose world comes crashing down when he is left at the altar. The comic possibilities are endless for a performer who is heartbroken to the point of derangement, yet is still forced to celebrate other people's love at their weddings. 

But, slowly, Robbie begins to heal, thanks in no small part to his growing friendship with the adorable Julia (Drew Barrymore), who works as a waitress at the same reception hall where he performs. Their romance is unbelievably endearing. It doesn't seem like it should work, but it does. Barrymore's presence seems to bring out something a little less scream-y in Sandler, and they would go on to make two more movies together ("50 First Dates" in 2004 and "Blended" in 2014).

The Wedding Banquet

In "The Wedding Banquet," nothing is quite as it seems. Wai-Tung Gao (Winston Chao) has reached an age where his conservative Taiwanese parents are growing impatient for him to finally get married, although their high standards for a daughter-in-law prove to be a difficult challenge to overcome. An even bigger issue: Wai-Tung is a gay man living happily with his partner Simon (Mitchel Lichtenstein), and has no intentions of marrying a woman even if she is a 5'9" opera singer with two PhDs who speaks five languages (his parents' requirements).

Wai-Tung thinks that staging a marriage of convenience with a mainland Chinese woman in need of a green card will solve all of his problems. He is, of course, as wrong as a person could possibly be. Only now-celebrated director Ang Lee's second film, "The Wedding Banquet" was well-received, earning an Academy Award nomination for best foreign language film and raising Lee's profile in Hollywood.

Waiting To Exhale

Often, romantic comedies focus on the bond between the main couple to such an extent that you start to wonder if either character has any other relationships in their life at all. They're frequently limited to one snarky best friend each — and if they're lucky, it's Judy Greer. "Waiting to Exhale" is different in many ways, partly because it highlights the friendship between a group of four women as they attempt to navigate a series of romantic misadventures. But it's also noteworthy because it's one of the rare mainstream movies from the 1990s that features a cast of four Black women who are the heroes of their own story, rather than sidekicsk in someone else's.

"Waiting to Exhale" is Forest Whittaker's directorial debut, and it was a significant financial success. It has also proven to have staying power: In November 2020, it was reported that ABC was developing a reboot of the film for television, produced by Lee Daniels.

Sleepless In Seattle

It would be impossible to make this list without including at least one entry from the decade's most famous romantic comedy duo: Meg Ryan and Tom Hanks. Together, they launched a charm offensive that leaves viewers powerless in its wake. Ryan and Hanks made three films together in the 1990s, each more successful than the last, but "Sleepless in Seattle" is the highlight of their shared filmography. 

Tom Hanks stars as Sam Baldwin, a widower who, a year and a half after his wife's death, is convinced by his young son to call into a radio show to talk openly about his grief. His vulnerability strikes a chord with listeners, chief among them Meg Ryan's Annie, who is engaged to another man but is nonetheless captivated by Sam's story. In a nod to "An Affair to Remember," Annie suggests that they meet at the observation deck of the Empire State Building. After a few snafus, they get their triumphantly romantic ending, earning a place for the Hanks-Ryan team in romcom history.

There's Something About Mary

Although Cameron Diaz has since stepped away from the acting business, when she was at the top of her game, there was no one who could touch her. "There's Something About Mary" highlights her skills as a romantic lead as well as a comedian in her own right, starring as the titular Mary who can't help but make men fall in love with her. Ben Stiller's Ted has been mooning over Mary since they were in high school, when a chance at a dream prom night was ruined by an unfortunate zipper accident. Hoping to have another chance with her, he hires a private investigator to track her down. 

The only problem (besides the fact that Ted's behavior probably qualifies as stalking)? It seems like every man in Mary's life is harboring a crippling infatuation with her. The private investigator starts to fall in love with her. A local pizza boy plays a long con, pretending to be a mild-mannered British architect just to be interesting enough to win her heart. How is Ted supposed to get close to Mary with this chaos whirling around them? A modern-day comedy of errors, "There's Something About Mary" dominated the late 1990s romcom market by ditching the sentimentality in favor of good old-fashioned cynicism.

How Stella Got Her Groove Back

All hail Angela Bassett; we are truly not worthy. Bassett stars in "How Stella Got Her Groove Back," a steamy romantic comedy about a thriving single mother who has neglected her romantic life to take care of her son and her career. On the advice of her friend (Whoopi Goldberg), she takes a relaxing vacation to Jamaica, where she will presumably unwind and unplug from the responsibilities of her regular life. But while she's there, she ends up meeting Winston Shakespeare, a handsome local man 20 years her junior played by Taye Diggs in his film debut. And the sparks fly!

Angela Bassett is delightful in a role that is groundbreaking in numerous ways. It's rare that we get major Hollywood productions with a Black woman in the lead role, let alone one who is over 40 (practically geriatric in the eyes of studio executives) and romantically involved with a man who is significantly younger than her.

Double Happiness

In the 1990s, we started to see more romantic films that would reckon with the immigrant experience, and more specifically, how the first-generation children of immigrants struggle to bridge the traditions of their parents with the very different world they've grown up in. "Double Happiness" stars a young Sandra Oh as an aspiring actress whose efforts to live up to the expectations of her parents are frequently at odds with her own desires. 

She leads a double life, trying to cultivate both the Chinese and Canadian parts of herself. This only becomes more complicated when she begins a tentative relationship with a white Canadian man, crossing a boundary that got her older brother disowned by their parents. "Double Happiness" is Sandra Oh's feature film debut, and it would garner major attention for the now critically-lauded actress.

10 Things I Hate About You

A modern-day take on "The Taming of the Shrew," "10 Things I Hate About You" is pretty much the gold standard for adapting William Shakespeare for the present day. Julia Stiles and Larisa Oleynik star as the daughters of a strict and overprotective father who creates a house rule that one sister can only date a boy when the other does. But that's a big problem for the bubbly, popular Bianca (Oleynik): Her older sister Kat (Stiles) has pretty much sworn off men, and is thus unlikely to be dating anytime soon.

There is a way around this, though. Cameron (Joseph Gordon-Levitt) has a huge crush on Bianca, so he comes up with a scheme to pay Patrick (Heath Ledger) to go out with Kat, leaving Bianca free to date. It works out exactly as well as you would expect, but watching it unfold is an utter delight. More than anything else, "10 Things I Hate About You" stands as a testament to the pure charisma that Heath Ledger had, even in the first film he made after leaving Australia for America.

Benny & Joon

Back before Tim Burton and Johnny Depp's codependent filmmaking relationship made the actor into a parody of himself, Depp starred in a series of quirky independent films, the most fun of which is "Benny & Joon." Mary Stuart Masterson plays Joon, a young woman with schizophrenia who is largely dependent on her older brother and caretaker, Benny (Aidan Quinn). In a losing hand of poker, she accidentally offers their home as a refuge for a friend's illiterate cousin, Sam (Depp). 

Sam is a man of few words, but he's incredibly adept at physical comedy, revering the likes of Chaplin, Keaton, and Harold Lloyd. The two become attached to one another very quickly, much to Benny's consternation, as he must find a way to make sure that Joon gets the care that she needs while giving her some sense of autonomy. "Benny & Joon" isn't perfect. It belongs to a long line of Hollywood films that trivialize mental illness by making it seem like a harmless quirk. But the unaffected, sweet performances from Masterson and Depp make it still worth watching.

But I'm A Cheerleader

When Megan's (Natasha Lyonne) parents and friends stage an intervention because they believe her to be a lesbian, she's flummoxed. How could that be? She has a boyfriend. She's a cheerleader, for heaven's sake! She's even more flummoxed when they send her away to a conversion therapy camp called True Directions, run by a scenery-chewing Cathy Moriarty, where she will supposedly rediscover her heterosexuality.

"But I'm a Cheerleader" is spectacularly unsubtle social satire, which director Jamie Babbit said in a Nitrate Online interview was intended to "poke fun at the Religious Right, but also at my own community."

The aesthetic of "But I'm a Cheerleader" is bright and vibrant, almost annoyingly so. The scenes at the conversion camp are an overload of pink and blue, giving off the vibes of the his and hers quarters of a Barbie Dream House. The candy-colored visual palette reflects the film's exaggerated, distorted depiction of gender roles, acting like a funhouse mirror held up to the expectations of what gay and straight people are supposed to look and act like.

Blast From The Past

As we currently enjoy a veritable Brendan Fraser renaissance, it seems as good a time as any to champion one of his best romantic comedies of the 1990s, "Blast from the Past." In the middle of the Cold War, a paranoid scientist (Christopher Walken) builds a fallout shelter under his home. When a plane crashes in their backyard, he assumes a bomb has fallen, and shepherds his very pregnant wife (Sissy Spacek) to safety, locking the doors behind them and making them live underground for the next 30 years. 

Adam (Fraser) is born and grows up in the fallout shelter, only leaving when his father has a heart attack and the family must rely on him to find supplies above ground. It's there that he meets Eve (Alicia Silverstone), who is less than charmed by his naivety, which borders on creepiness, but who comes around when she fully appreciates the fact that, well ... it's Brendan Fraser. "Blast From the Past" underperformed at the box office, but in the years since has grown in fans' estimation, remembered fondly by audiences who are only now rediscovering it.

Notting Hill

If Tom Hanks was the king of affable 1990s romantic comedies, Hugh Grant was his roguish, dreamy younger brother. In "Notting Hill," he is paired up with Julia Roberts, creating an international rom-com power couple for the ages. When American movie star Anna Scott (Roberts) wanders into William Thacker's (Grant) independent bookshop, a chance encounter ends up embroiling both in an unexpected romance. But dating one of the most famous people in the world is more complicated than it seems, and there are plenty of problems for the new couple to overcome.

At this point in his career, Hugh Grant could have convincing romantic chemistry with a cantaloupe; the floppy-haired, perpetually befuddled Englishman is at the peak of his personal charm. Ditto for Julia Roberts, who in the late 1990s was the highest-paid actress in the world. So, getting the two of them together is basically a dream scenario for a romantic comedy. And audiences responded in kind: When it was released in May 1999, "Notting Hill" quickly became the highest-grossing British film of all time.

While You Were Sleeping

Sandra Bullock gets up to a lot of crazy hijinks in 1990s romantic comedies, but probably the most bizarre is when she poses as the fiancée of a man in a coma, then accidentally falls in love with his brother, played by Bill Pullman. (Don't you hate it when that happens?) Really, the whole fiasco unfolds like a slow-moving train wreck: Bullock plays a desperately lonely transportation worker who develops a crush on a handsome commuter she sees on his way to work day after day. 

After acting quickly to save his life, Bullock's character makes a thoughtless comment to his panicked family that betrays how well she knows him, making them assume the two were romantically involved. And, in true "Dear Evan Hansen" fashion, she does nothing to convince them otherwise. Look, it could happen to anyone. Despite its fairly ridiculous premise, Bullock and Pullman sell the burgeoning relationship between their characters, and "While You Were Sleeping" would end up being nominated for AFI's 100 Years ... 100 Passions list for their efforts (although, sadly, it didn't make the final cut).

The Cutting Edge

There aren't a ton of sports movie romcoms, so when you find one, you have to cling to it with both arms and refuse to let it go. That's why we're willing to accept "The Cutting Edge," even with its not inconsiderable flaws. Moira Kelly stars as an uptight figure skater who has run through pretty much every single male skating partner in the business because of her demanding behavior on the ice. 

Staring down an upcoming Olympics, her only chance is the clumsy, boorish Doug Doursey (D. B. Sweeney), who was forced to kiss his professional hockey career goodbye after a serious head injury damaged his peripheral vision. The two butt heads for quite some time, their styles and general personalities totally at odds with one another, until they finally begin to develop a begrudging respect and affection for each other. "The Cutting Edge" is heavy with the cheese, but somehow manages to be endearing almost in spite of itself.

The Preacher's Wife

A 1996 release, "The Preacher's Wife" would serve as Penny Marshall's penultimate directorial effort after a string of box office successes in the late 1980s and early 1990s. "The Preacher's Wife" was a remake of a 1947 film of the same name, with Cary Grant and Loretta Young in the lead roles. When Reverend Henry Biggs loses faith in his ability to reach his parishioners, he prays to God for help. God obliges by sending a charming angel (Denzel Washington), who develops an immediate connection with the reverend's wife, Julia, played by Whitney Houston. 

Although they are both clearly smitten with one another, their romance remains above board throughout the film, tinged with a bittersweet regret. "The Preacher's Wife" received an Academy Award nomination for best original score, but the biggest success of the film was its soundtrack, which was the highest-selling gospel album of all time.

Dilwale Dulhania Le Jayenge

A modern take on the Rostand play "Cyrano de Bergerac," "The Truth About Cats & Dogs" brings the classic tale of insecurity into the present day. Janeane Garofalo plays a veterinarian and radio host who is confident in her advice about pets, but less so in her appearance. When a charming caller invites her out to lunch, she panics at the prospect of meeting him and convinces her beautiful neighbor (Uma Thurman) to pose as her. Their web of deceit takes on new dimensions as all three characters become more committed to the bizarre, fraudulent relationship.

Star Garofalo has gone on the record with the A.V. Club, saying that she dislikes the way the film ended up, saying, "I think it's soft and corny, and the soundtrack makes you want to puke, and everybody's dressed in Banana Republic clothing ... It was originally supposed to be a small-budget independent film where there would be much more complexity to all the characters, and Abby and the guy don't wind up together at the end." Still, for better or worse, its appeal amongst mainstream audiences is clear.

The Truth About Cats & Dogs

A modern take on the Rostand play "Cyrano de Bergerac," "The Truth About Cats & Dogs" brings the classic tale of insecurity into the present day. Janeane Garofalo plays a veterinarian and radio host who is confident in her advice about pets, but less so in her appearance. When a charming caller invites her out to lunch, she panics at the prospect of meeting him and convinces her beautiful neighbor (Uma Thurman) to pose as her. Their web of deceit takes on new dimensions as all three characters become more committed to bizarre, fraudulent relationship.

Star Garofalo has gone on the record with the AV Club that she dislikes the way the film ended up, saying, "I think it's soft and corny, and the soundtrack makes you want to puke, and everybody's dressed in Banana Republic clothing ... It was originally supposed to be a small-budget independent film where there would be much more complexity to all the characters, and Abby and the guy don't wind up together at the end." Still, for better or worse its appeal amongst mainstream audiences is clear.

Sliding Doors

It seems like all of life is filled with missed connections and tantalizing "what ifs." So, it makes sense that, at some point, someone would make a romantic comedy exploring the two different paths that a person's life could take based on one single divergence. In the case of "Sliding Doors," it's the simple act of making a train before the doors close, or missing it and having to wait for the next one. Gwyneth Paltrow plays Helen, a woman who has just been fired from her PR job and dejectedly returns home on the London underground. 

In one timeline, she makes the train and gets home in time to see her boyfriend cheating on her. In the other, she doesn't, and remains blissfully unaware of his indiscretions. From there, the two versions of Helen have lives that become dramatically different from one another, as a result of this seemingly insignificant moment in life. Filmed creatively with charming performances from Paltrow and her costar John Hannah, "Sliding Doors" is one of the most intellectually interesting 1990s romantic comedies.

Read this next: The 15 Best Jane Austen Adaptations Ranked

The post The 20 Best '90s Romantic Comedies Ranked appeared first on /Film.