From ancient Greek tales to Shakespeare to Jane Austen, the best romantic comedies had a long road before becoming a staple genre of cinema. By the 1990s, rom-coms were in top form, with top-notch directors imprinting their artistic visions. But of all the romantic comedies to release from 1990 to 1999, which are most deserving to be considered the greatest of all time?
While the years spanning the tail end of Hollywood's Golden Age up to the post-American New Wave 1980s shaped modern rom-coms, the genre's tropes and conventions were spit-shined to perfection throughout the '90s. A slew of new stars emerged to become the genre's most recurring faces, whilst the independent scene ushered in more exciting storytellers, especially those from the queer community. You might roll your eyes at the genre's overreliance on licensed music during this time, but you can't deny a few rom-com soundtracks wound up in your boomboxes. These films helped shape pop culture, and you can't escape them.
So, gtet on those acid wash jeans, put on that vintage leather jacket, and cue up some Sixpence None the Richer – here are the 33 greatest '90s rom-coms ever to grace the big screen.
33. The Wedding Banquet
Year: 1993
Director: Ang Lee
Ang Lee's bilingual queer classic The Wedding Banquet is a rom-com that mines humor in the reconciliation of Eastern and Western values. Winston Chao, in his film debut, plays a bisexual Taiwanese immigrant who lives blissfully with his gay Jewish partner (Mitchell Lichtenstein) in New York. Chao's Gao Wai-Tung marries a Chinese woman (May Chin) both to placate his parents and to help the woman obtain a green card. But what should have been a painless farce gets more complicated when Gao's parents arrive to arrange an elaborate banquet. An upbeat comedy representing the immigrant and LGBTQ experiences at a precarious time, The Wedding Banquet offers plenty of laughs with sweet-and-sour humor.
32. Emma
Year: 1996
Director: Douglas McGrath
Gwyneth Paltrow brings to life Jane Austen's feisty Emma Woodhouse to life in Douglas McGrath's adaptation of Emma. The breezy period rom-com sees Paltrow play a wealthy young woman in the 19th century who delights in playing romantic matchmaker for her friends, never mind that she's actually terrible at it. She's also terrible at recognizing her own budding feelings for gentle Mr. Knightley (Jeremy Northam). While a BBC version of Emma starring Kate Beckinsale, also released in 1996, was compared more favorably by critics than Paltrow's movie, Emma is still a charmer.
31. Never Been Kissed
Year: 1999
Director: Raja Gosnell
You'll need a lot of suspension of disbelief to accept that Drew Barrymore, playing a socially awkward 25-year-old copy editor for the Chicago Sun-Times, can pass off as a high school teenager. But Raja Gosnell's Never Been Kissed is worth getting swept away for. Barrymore stars as Josie, an ambitious but socially reclusive journalist who is assigned a major story to go undercover at a high school. While the experience starts to unlock old traumas and Josie struggles to keep up her double life, she soon falls for the handsome English teacher (Michael Vartan). Never Been Kissed is sugary Hollywood fluff, but Barrymore is enchanting as a young woman who, however past due, finally learns to grow up.
30. Blast From the Past
Year: 1999
Director: Hugh Wilson
What would you do if you spent most of your life in a Cold War-era bomb shelter and ventured to the outside world for the first time? For Brendan Fraser, he falls in love with sly, snarky Alicia Silverstone. In Blasts From the Past, Fraser plays a man raised by his anti-Communist parents (Christopher Walken and Sissy Spacek) who chose to hole up in a fallout shelter in fear of the Cold War. When Fraser's Adam is allowed to walk out, he meets jaded Eve (Silverstone), who acclimates him to the modern world. Blast From the Past isn't ambitious, but it's a fun fish-out-of-water comedy with a sweet romance.
29. Addicted to Love
Year: 1997
Director: Griffin Dunne
If Wong Kar-wai's In the Mood for Love was ten times less haunted in its yearning and a tiny bit funnier, it might look like Addicted to Love. Heartbroken Sam (Matthew Broderick) and resentful but cool motorcyclist Maggie (Meg Ryan) are two people whose respective partners are now dating each other. As Sam and Maggie conspire to break up their exes, they realize their own attraction for each other. A jealousy-fueled rom-com with a touch of dark humor, Addicted to Love is an underrated standout from the '90s with a delightfully vinegary Meg Ryan.
28. One Fine Day
Year: 1996
Director: Michael Hoffman
George Clooney was still a TV heartthrob when, around 1996, he began making serious waves as a movie star. That year, Clooney co-starred with Michelle Pfeiffer in the delightful rom-com One Fine Day. The stars play single parents who spend one hectic day together, balancing their demanding jobs while babysitting for each other after their kids miss a school field trip. Amid a whirlwind day of comic mishaps, they start to become closer than they could have ever imagined when they woke up that morning. While Pfeiffer is predictably great, it's Clooney who emerges as a star in the making, proving his big screen chops in this understated romantic comedy.
27. Edge of Seventeen
Year: 1998
Director: David Moreton
A tip of the hat to Annie Lennox and Eurythmics for "17 Again." David Moreton's queer coming-of-age rom-com Edge of Seventeen has mostly slipped through the cracks of the '90s rom-com canon, but like buried treasure, it is waiting to be rediscovered. Set in 1984, Chris Stafford plays high school teenager Eric, who is coming to grips with his sexual identity and first encounters with male romance. Amid his first heartbreak, Eric falls back on his friends for support, including best friend Maggie (Tina Holmes) and his own mother, who is trying to understand him. Edge of Seventeen is a sensitive portrait of the turbulence of adolescence, aided by a glorious throwback soundtrack.
26. Joe Versus the Volcano
Year: 1990
Director: John Patrick Shanley
The first of several movies starring Tom Hanks and Meg Ryan is also the strangest of them all. In Joe Versus the Volcano, released in 1990, Hanks plays hypochondriac Joe, who learns he has a terminal illness – a "brain cloud." With his final months ahead of him, Joe accepts an offer to sacrifice himself to a volcano in the South Pacific on behalf of superstitious natives. Along the precarious way to the island, he falls in love with Patricia (Meg Ryan, who plays two other roles in the movie), who helps Joe get a new lease on life. Joe Versus the Volcano didn't become as big a hit as Hanks and Ryan's later movies, but its blend of screwball energy and existential introspection makes it unusually compelling.
25. There's Something About Mary
Year: 1998
Director(s): Peter Farrelly, Bobby Farrelly
If you could have a do-over with a dream prom date, would you? That's the dilemma faced by Ted (Ben Stiller), a magazine writer who still pines for Mary (Cameron Diaz) years after a hilarious and painful bathroom mishap causes him to miss their date. Now, years later, the two reunite as adults, only for Ted to find himself competing with the sleazy private eye (Matt Dillon) he hired to find her. (Oh, the days before social media.) A sweet romance brimming with moments on the more risque side of things, there's a lot to love about There's Something About Mary.
24. French Kiss
Year: 1995
Director: Lawrence Kasdan
And now, for something different from Star Wars and Indiana Jones director Lawrence Kasdan. Released in 1995, French Kiss stars Meg Ryan as an American woman whose intentions to fly to France and confront her wayward fiance gets derailed when a charming crook (Kevin Kline) uses her bags to smuggle a stolen diamond necklace. As the crook chases her all around the city of love, sparks fly as Meg Ryan's heartbroken history teacher opens up to a whole new beginning. French Kiss was hit with mediocre reviews upon release in 1995, but Kasdan's clever comic subtlety and reliable performances by Ryan and Kline (whose French accent is legitimately hilarious) make it worth touring all these years later.
23. Shakespeare in Love
Year: 1998
Director: John Madden
While its legacy is tainted by an overwhelming Oscars campaign supported by Harvey Weinstein, Shakespeare in Love remains a delightful feast for any fan of the Bard. Joseph Fiennes plays a young William Shakespeare who is not yet the famous playwright he is destined to be. John Madden's picturesque comedy supposes Shakespeare will find all the inspiration he needs in his forbidden love affair with a noblewoman, Viola de Lesseps (Gwyneth Paltrow). An enchanting star-crossed romance that ingeniously alludes to Shakespeare's plays, Shakespeare in Love is a beautiful and witty costume rom-com. If it weren't for the fact it went up against Saving Private Ryan (aka one of the best war movies ever made) at the Oscars and won it might be more embraced today.
22. Fools Rush In
Year: 1997
Director: Andy Tennant
One-night stands, surprise pregnancies, and New York hot dogs – Fools Rush In is a tender rom-com about falling in love in reverse. Matthew Perry stars as straight-laced New York architect Alex, whose encounter with a free-spirited photographer, Isabel (Salma Hayek) in Las Vegas results in a pregnancy. As the two decide to pursue a relationship, they encounter roadblocks to happiness, from long distances to Isabel's crestfallen father. Critics were not won over by Fools Rush In during its initial release, but the movie has stood the test of time to endear itself to a loyal audience. Circa 2022, Matthew Perry shared on his Instagram page that he considered Fools Rush In his "best movie." A year later, Hayek thanked him in belated gratitude after Perry died in 2023.
21. Sense and Sensibility
Year: 1995
Director: Ang Lee
Jane Austen is the mother of all romantic comedies, with her beloved canon of novels enjoying relevance even hundreds of years later as some of the best rom-coms around. In 1995, Ang Lee brought to the screen Austen's debut novel Sense and Sensibility, its story centered on the Dashwood sisters (played by Emma Thompson, who also wrote the screenplay, and Kate Winslet) who seek to marry after their father's passing tanks their fortune. Lee's delicate and graceful adaptation keeps all the romance, wit, and heartfelt depth of Austen's story to be one of the definitive cinematic versions of her works yet.
20. The Wedding Singer
Year: 1998
Director: Frank Coraci
Adam Sandler doesn't sacrifice an ounce of his crass humor for The Wedding Singer, yet he's singing in tune in this shockingly sweet romantic comedy. Set in 1985, Sandler stars as a professional wedding singer who begins to spiral after being left at the altar himself. Soon, he falls for a waitress, played by Drew Barrymore, and takes it upon himself to stop her from getting hitched. While The Wedding Singer is peak Sandler, there's plenty of range to the movie than its simple looks appear.
19. Only You
Year: 1994
Director: Norman Jewison
Years before they were in the Marvel Cinematic Universe, Marisa Tomei and Robert Downey Jr. were destined lovers in Only You. This 1994 rom-com follows Faith (Tomei), whose adolescent horsing around with a Ouija board gave her the name "Damon Bradley" as the man she is meant to marry. Years later and days before her wedding, Faith receives a call from her fiance's old classmate – none other than Damon Bradley. Along the way, she meets a man named Peter (Downey Jr.). who further complicates Faith's destiny. A movie about having, ahem, faith in the stars, Only You is magically hilarious.
18. Runaway Bride
Year: 1999
Director: Garry Marshall
There's being indecisive, and there's being Julia Roberts in Runaway Bride. In Gary Marshall's scenic and easy-breezy romantic comedy, Richard Gere plays a smart-aleck New York newspaper journalist who travels to a small town in Maryland where a young woman, Maggie Carpenter (Roberts) has left multiple men behind at the altar, making her a local legend. As Gere's Ike collects interviews and insight for a human interest piece, he starts to fall for the woman who can't stand still. While Runaway Bride might test your patience, Gere and Roberts make a winning onscreen couple whose romance can make you run wild.
17. While You Were Sleeping
Year: 1995
Director: Jon Turteltaub
Sandra Bullock's stardom had become unstoppable after Speed, but While You Were Sleeping sees the newly-christened Hollywood heroine slow down for a movie where fantasies and reality clash. Bullock stars as Lucy, a lonely transit employee who saves her crush Peter (Peter Gallagher) from a fatal accident. When Peter falls into a coma, Lucy is mistakenly introduced as Peter's fiance to his family, which allows her to get close to Peter's brother (Bill Pullman). Are you willing to sacrifice living out your dreams for the confidence of knowing the real thing? Such a relatable dilemma made While You Were Sleeping a box office hit in 1995, amassing an impressive $182 million worldwide.
16. Chasing Amy
Year: 1997
Director: Kevin Smith
After Clerks and Mallrats, Kevin Smith showed off a new level of artistic maturity in his romantic dramedy Chasing Amy. Ben Affleck leads as a New Jersey comic book artist who falls for enchanting – and gay – Alyssa Jones (Joey Lauren Adams). As the two get close, Alyssa questions her sexuality and willingness to be with Affleck's Holden, while Holden grapples with Alyssa's promiscuous history. While Chasing Amy inspires debate over its sexual politics, it remains one of the best movies in Smith's oeuvre and one of the best rom-coms of the '90s, thanks to its gritty textures and naked honesty about love and infatuation.
15. She's All That
Year: 1999
Director: Robert Iscove
George Bernard Shaw's Pygmalion and George Cukor's 1964 movie My Fair Lady get a late '90s makeover in the millennial classic She's All That. After getting dumped by his girlfriend, popular jock Zack (Freddie Prinze Jr.) accepts a challenge issued by his best friend to transform unpopular art student Laney (Rachael Leigh Cook) into a bonafide prom queen in just six weeks. Naturally, and inevitably, their feelings for each other start to become real while Laney begins blossoming out of her shell. With charismatic leads, Usher in the small role of the school's radio DJ, and an ace needle-drop in "Kiss Me" by Sixpence None the Richer, She's All That finds itself in the canon of the all-time best teen movies and greatest rom-coms of the decade.
14. Sabrina
Year: 1995
Director: Sydney Pollack
In Sydney Pollack's 1995 remake of Billy Wilder's 1954 classic, Julia Ormond stars as the title heroine, Sabrina Fairchild, daughter to a chauffeur who tends to the affluent Larrabee family on Long Island. As Sabrina harbors unrequited feelings for young David Larrabee (Greg Kinnear), she travels to Paris and transforms into an elegant young woman – confident enough to steal David away. But as David's older brother Linus (Harrison Ford) tries to stop Sabrina and David from getting together, he arrives at the realization that he has feelings of his own. Although there's no outdoing Billy Wilder's original, Pollack's '95 remake is enchanting in its own way.
13. But I'm a Cheerleader
Year: 1999
Director: Jamie Babbit
Jamie Babbit's queer teen rom-com But I'm a Cheerleader was wildly misunderstood during its original release in 1999. But time has been kind to Babbit's film, with a dedicated cult following who embrace it as a transgressive genre gem. Natasha Lyonne is Megan Bloomfield, a high school cheerleader who is sent away by her parents to a conversion therapy camp to "cure" her budding lesbianism, only for her to fall for acerbic fellow patient Graham (Clea DuVall). With its tongue firmly in cheek, But I'm a Cheerleader relishes its satire of gender norms with eye-popping color and set design that makes a living doll house feel like a prison.
12. My Best Friend's Wedding
Year: 1997
Director: P. J. Hogan
My Best Friend's Wedding would be the platonic ideal for a '90s romantic comedy if it weren't for its surprisingly honest and unexpected ending. Julia Roberts is at the height of her stardom as a New York food critic who grows distraught after she learns her longtime male best friend (Dermont Mulroney) is set to get married. (Cameron Diaz co-stars as the bubbly fiance, Kimmy.) Roberts' Jules Potter grows determined to stop the wedding, but in the end, nothing can stop true love. Joyous and feel-good, My Best Friend's Wedding will have you saying a little prayer.
11. Singles
Year: 1992
Director: Cameron Crowe
Cameron Crowe's Singles is an ensemble rom-com that masterfully captures the grunge zeitgeist of the early 1990s. In this ode to love and rock 'n roll, a couple of twentysomethings living in Seattle navigate the ups and downs of their relationships, all of it set against the emergence of grunge in the city that spawned it. Leading Singles are Bridget Fonda, playing a coffee bar waitress, and Matt Dillon an aspiring but aloof frontman of a grunge rock band. With its unparalleled display of raw feelings and a monster soundtrack that effectively packaged alternative rock onto the mainstream, Singles utterly shreds.
10. As Good As It Gets
Year: 1997
Director: James L. Brooks
Jack Nicholson and Helen Hunt both took home Oscars for their performances in James L. Brooks' As Good As It Gets, and it's not hard to see why. Nicholson stars as a misanthropic writer whose world is interrupted when he's asked to care for a neighbor's dog. This sets off a domino effect that puts him into the orbit of a beautiful waitress (Hunt), with whom he strikes up an unusual romance. As Good As It Gets doesn't reinvent the rom-com wheel, but its sharp script, emotional heft, and stirring performances by its leads – not to mention being another solid New York-centric romance – makes it even better than you might realize.
9. Boomerang
Year: 1992
Director: Reginald Hudlin
Reginald Hudlin's playful romantic comedy Boomerang was a new vehicle for Eddie Murphy to flex different muscles as a leading man. The comedian stars as Marcus, a suave, womanizing ad executive whose formidable new boss (Robin Givens) takes him down a peg. As Marcus experiences his first real heartbreak, he reboots and becomes a new man, with a strengthening connection to kind coworker Angela (Halle Berry). While Boomerang was a modest hit at the box office, critics weren't so enamored by Hudlin's effort. But the movie has won more respect in hindsight, being recognized by Entertainment Weekly as an underappreciated genre classic in 2019.
8. 10 Things I Hate About You
Year: 1999
Director: Gil Junger
Shakespeare's The Taming of the Shrew gets a late '90s makeover in the teen comedy classic 10 Things I Hate About You. Julia Stiles plays an antisocial, totally un-dateable high schooler who is wooed by the bad boy of the hallways (Heath Ledger in a breakout performance). But while Patrick is paid to date her by her sister's boyfriend (Joseph Gordon-Levitt), feelings become real. 10 Things I Hate About You was a hit during its release and has only become more loved over time, being considered a titan of a rom-com that challenged the genre's established archetypes and promoted a progressive point of view. To this day, it's still considered as one of the best '90s movies ever made, and for good reason.
7. You've Got Mail
Year: 1998
Director: Nora Ephron
When America went online, there was love in the chat rooms. In this update to the 1940 classic The Shop Around the Corner, Nora Ephron's You've Got Mail pairs Meg Ryan, playing a small bookshop owner in a virtual (and anonymous) romance with Tom Hanks, as the owner and executive of a successful bookstore franchise. While its contemporary setting has made it an accidental period movie in retrospect – set at the beginning of the dotcom bubble and the amassing power of franchises over family businesses – Ephron's witty scriptwriting and warm storytelling make You've Got Mail feel like you're walking around New York City in the fall.
6. Sleepless in Seattle
Year: 1993
Director: Nora Ephron
In Nora Ephron's giant of a romantic comedy, Tom Hanks stars as a Seattle-based widower whose son's call to a popular radio station on behalf of his dad becomes a cultural sensation, attracting the attention of a Baltimore journalist (Meg Ryan) stuck in a loveless engagement. Sleepless in Seattle is a movie for the most hopeless of romantics, a classic that testifies to the worthwhile effort of opening up your heart to someone else – and the sheer luck of eerily good timing. Sleepless in Seattle was a hit in 1993, but reverence for it has only strengthened over time. That's in spite of the fact the two leads don't meet until the movie is almost over.
5. Jerry Maguire
Year: 1996
Director: Cameron Crowe
When Cuba Gooding Jr. tells Tom Cruise to show him the money, indeed he did: This '96 smash hit by director Cameron Crowe grossed a mighty $273 million at the box office. But all that money shows is just how much audiences loved Jerry Maguire. Inspired by the '93 NFL season that introduced free agency and Jeffery Katzenberg's infamous memo to Disney in 1991, Jerry Maguire sees Cruise as a sports agent whose epiphany about his work leads him to strike out on his own, supported only by a single mother (Renée Zellweger) and his only client (Gooding Jr.). While primarily a sports movie that unfolds on the sidelines, Jerry Maguire also swoons as a romance between Cruise's and Zellweger's characters, birthing immortal lines like "You had me at 'hello.'"
4. Four Weddings and a Funeral
Year: 1994
Director: Mike Newell
Mike Newell's Four Weddings and a Funeral did more than launch Hugh Grant to international stardom. It was and still is a staple of British pop culture and is widely recognized as one of the greatest British movies of all time. Grant leads the film as the charming but commitment-averse Charles, who keeps running into the beautiful Carrie (Andie MacDowell) at different weddings and one funeral. Charles is desperate to confess his feelings to Carrie – if only he weren't standing in his own way. Buoyed by witty dialogue and a star-making performance by Grant, Four Weddings and a Funeral will have you saying "I Do" until death do you part.
3. Notting Hill
Year: 1999
Director: Roger Michell
What if you could fall in love with a movie star? Roger Mitchell explores the ultimate "What if?" fantasy in the budding romance between Hugh Grant who falls in love with movie star Anna Scott (Julia Roberts) after an unsuspecting visit to his understated English bookstore. As Roberts' Anna and Grant's Will date, they encounter challenges that remind them they live in completely different worlds. But sure enough, the two earn their Hollywood ending. With a dreamlike quality and a jolly sense of humor, Notting Hill is the rare rom-com that makes you think love can find you when you least expect it.
2. Before Sunrise
Year: 1995
Director: Richard Linklater
If you've ever been lucky enough to spend just one night with someone you were meant to spend it with, that's the feeling you'll find in Richard Linklater's revered '95 romantic comedy Before Sunrise. Ethan Hawke and Julie Delpy play strangers aboard a train to Vienna who catch each other's eyes and embark on a spontaneous, whirlwind date in Vienna. Through heartfelt conversations and intimate listening in record stores, Before Sunrise captures the thrill of finding that one person that you might not ever see again but can picture spending a whole life with together forever.
1. Pretty Woman
Year: 1990
Director: Garry Marshall
Julia Roberts and Richard Gere lead the ultimate sweep-off-your-feet romantic comedy that topped the box office and catapulted Roberts to fame. Roberts shines as Vivian Ward, a free-spirited prostitute who is hired by a wealthy businessman (Gere) to accompany him for a week of events, only for the two to fall in love despite their disparate worlds and contrasting ideas about love and happiness. While originally conceived as a dark drama, Pretty Woman's Pygmalion-esque fairy tale is just the stuff Hollywood is made of. There's simply never been another movie like it, and there may never be again.
