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The 25 Most Timeless Romance Movies from the 1990s

Richard Wells

Mar 1, 2024 — 17 min read

Best Romance Films Of The 1990's

The 1990s gifted us with some of the most iconic and unforgettable romance films that still make us swoon with their chemistry and stories of love against all odds. As a seasoned film critic who has watched my fair share of rom-coms and tearjerkers, I have compiled the definitive list of the 25 best romance movies from that decade.

From passionate affairs abroad like "Before Sunrise" to feel good favourites such as "You've Got Mail," the 1990s struck a balance between charming romantic comedies and emotional dramas that made us laugh, cry, and believe in movie magic. While the stories may seem far-fetched, the raw emotions and connections between the characters transport us into their world, where love prevails despite circumstance.

Before Sunrise (1995)

As I watched "Before Sunrise" unfold with my sceptical eye, I found myself unexpectedly moved by the natural chemistry between strangers-turned-lovers Jesse and Celine. What begins as a chance encounter on a train turns into a magical night in Vienna "before sunrise," walking the cobblestone streets while conversation flows effortlessly between Ethan Hawke and Julie Delpy. As the sun peaks over the horizon, so ends their short but meaningful time together, with promises to meet again that pull on the heartstrings.

"I believe if there's any kind of God it wouldn't be in any of us, not you or me but just this little space in between. If there's any kind of magic in this world it must be in the attempt of understanding someone, sharing something." - Before Sunrise

Jerry Maguire (1996)

Another unlikely romance springs up between a single mother and a newly independent sports agent floundering to find his moral compass in Cameron Crowe’s "Jerry Maguire." As Jerry Maguire navigates career upheaval after a crisis of conscience, Renée Zellweger is a breath of fresh air as the guileless Dorothy Boyd, who chooses to stand by her man despite mounting uncertainty.

Their relationship grows from professional to personal, with an undeniable sweetness at its core, as they support each other’s dreams: Jerry to start his own agency and Dorothy to achieve security for her son. Cuba Gooding, Jr. is also a showstopper as Rod Tidwell, an arrogant football star whose lovable arrogance steals every scene. Altogether, the stellar cast and Crowe’s keen direction earned "Jerry Maguire" critical acclaim and 5 Oscar nominations, including Best Picture and Best Actor for Tom Cruise.

The Bridges of Madison County (1995)

Four-time Academy Award winner Clint Eastwood tries his seasoned hand at directing a romance and delivers an understated yet emotionally resonant love story in "The Bridges of Madison County." Sparks fly between Eastwood himself as a National Geographic photographer passing through a small town in Iowa and Meryl Streep as an Italian war bride now living an ordinary life as a farmer’s wife.

Their four-day love affair is brief but intense, calling into question duty versus desire and whether such short-lived passion can truly consider what would have been. Streep considered it one of her most challenging acting roles, having to portray a plain housewife opposite the iconic Eastwood. But their on-screen intimacy draws viewers in to root for their union despite impracticalities. With $182 million worldwide against its modest $30 million budget, this mature romance clearly resonated strongly with audiences.

Notting Hill (1999)

One of my favourite actors, Hugh Grant, shines in a charming British romantic comedy, "Notting Hill.” Grant is in fine form as William Thacker, a bumbling, awkward owner of a travel bookshop in London whose humdrum world collides with fame and fortune when Hollywood superstar Anna Scott, played by none other than Julia Roberts herself, wanders into his shop.

Their mutual attraction seems doomed from the start, as the pressures of Anna’s stardom undermine ordinary William’s ability to win her affection amid paparazzi intrusion. But of course, true love eventually wins out in the final reel. With Grant’s signature debonair floppy hair and foppish English stammering contrasted by Roberts’ megawatt smile and glamorous swagger, "Notting Hill” became my favourite romantic comedy. And moviegoers clearly agreed, rocketing the film to $364 million worldwide and giving hope to everyday Joes by winning the heart of their celebrity crush against all odds.

Ghost (1990)

The iconic love story between Sam Wheat (Patrick Swayze) and Molly Jensen (Demi Moore) dazzles the mind and tugs the heartstrings with its unique supernatural premise. After Sam's untimely death, his ghost enlists the help of psychic Oda Mae Brown (Whoopi Goldberg) to protect Molly from his killers still at large. From hilarious hijinks to tear-jerking goodbyes, Goldberg grounds the film's whimsical concept with her comedic prowess, while Moore gives an emotional turn as the grieving widow.

But Swayze is the true heartbeat, making us ache for his impossible chance at reuniting with his lost love across the divide between life and the afterlife. "Ghost" strummed a cultural chord as the highest grossing film worldwide in 1990, earning critical praise and winning Goldberg a Best Supporting Actress Oscar for her role. Beyond the haunting love story, its iconic scenes and dialogue have ingrained "Ghost" into pop culture forever.

"It's amazing, Molly. The love inside, you take it with you."

You’ve Got Mail (1998)

Back in 1998, the internet was still a cultural novelty, so I found the concept of online romantic rivals turned secret virtual lovers to be quite inventive in Nora Ephron’s "You’ve Got Mail,” starring her resident rom-com darling duo, Meg Ryan and Tom Hanks. As the owner of a corporate book superstore, Hanks slowly takes over independent bookshop owner Ryan’s storefront without realising that the anonymous lady he’s been flirting with online is none other than his competition.

Of course, the truth reveals itself, and after some friction, the two reconcile in the end. Besides its clever premise foreshadowing online dating, Ryan and Hanks’ effortless rapport recaptured their magic first seen in 1993’s "Sleepless in Seattle,” making "You’ve Got Mail” a solid late ‘90s romance entry tapping into changing technology. With almost $250 million grossed worldwide, clearly audiences enjoyed returning to the Ryan/Hanks well, even if the story stretched believability. But we watch rom-coms to buy into fantasy, so I didn’t mind suspending some disbelief!

Beauty and the Beast (1991)

On the animated front, Disney struck gold again after "The Little Mermaid" with their adaptation of "Beauty and the Beast” in 1991, becoming the first animated film nominated for Best Picture. And for good reason! Belle remains one of Disney’s most independent minded and intelligent princesses, representing a new era. And who could forget the enthralling musical numbers like "Be Our Guest” and the soaring iconic ballad "Beauty and the Beast,” further deepening our investment in Beauty and the Beast’s tender love story unfolding through lush animation and important themes about recognising inner beauty beyond appearances - ones we still wrestle with today.

Add in memorable sidekick characters like Lumiere and Cogsworth, and "Beauty and the Beast” absolutely deserves its status as a groundbreaking animated film that inspired the Broadway musical and a live action remake starring Emma Watson later on. Simply put, Disney perfected their formula with this instant classic.

"If she is the one who can break the spell, they must start by learning to love."

Sleepless in Seattle (1993)

Catching lightning in a bottle once again in their hat trick of romance films, Tom Hanks and Meg Ryan deliver plenty of heart and charm with a nontraditional love story full of missed connections and fateful twists of circumstance. After widower Sam Baldwin (Hanks) pours his grief over losing his wife out on a national late night radio talk show, he captures the heart of Ryan’s Annie Reed all the way across the country in Seattle, leading her on a quest to meet her mysterious crush in-person on top of the Empire State Building.

The "An Affair to Remember” references warm this nostalgic romantic over, but what sells this sentiment is the soulful yearning in Ryan and Hanks’ performances as strangers searching for that perfect love to fill the void in their lives. On paper, the plot holds some far-fetched coincidences, but the end result simply works and stands the test of time as a fan-favourite romance. And with over $200 million grossed worldwide on a $21 million budget, many audiences back in 1993 agreed!

Out of Sight (1998)

Before her pop superstardom, Jennifer Lopez set her fiery mark in Hollywood alongside heavyweight George Clooney in Steven Soderbergh’s sexy crime caper "Out of Sight.” Sparks fly both literally and figuratively between Lopez’s U.S. Marshal Karen Sisco and Clooney’s escaped bank robber Jack Foley as they play an ongoing game of cat-and-mouse across state lines.

Their palpable attraction simmers every time they’re forced together against their better judgement. Both leads ooze movie star charisma with snappy dialogue and charged chemistry. And that famously steamy trunk scene alone doubled the temperature in any theatre! With its slick direction and cool retro style, "Out of Sight" brings the heat that makes this forbidden love affair so thrilling to watch unfold. Audiences clearly felt the same, making "Out of Sight” Lopez’s then highest grossing opening weekend for a film.

"You know, when you first came in, I thought you were going to be one of those real hardass lady cops."

My Best Friend’s Wedding (1997)

Back in 1997, I relished Julia Roberts flexing her rom-com prowess as Julianne Potter, a perpetual bachelorette who gets derailed from her unencumbered dating ways when she realises she’s actually in love with her best friend Michael (Dermot Mulroney) days before his wedding to the bubbly, slightly naive Kimmy (Cameron Diaz). What ensues is a hilarious battle of sabotage versus destiny, all leading up to a mad dash to stop the wedding... or not!

Roberts hits all the right notes, sliding from manic comedy to heartbreaking realisation for letting her chance at love pass by long ago. Her and Mulroney’s lived-in friendship chemistry lays the groundwork, while Diaz is adorable as his catty-turned-endearing bride-to-be. With Chicago serving as the perfect rom-com backdrop and a wedding scene for the ages, "My Best Friend’s Wedding captures all the best parts of the genre with Roberts at the top of her game.

“I'll say a little prayer for you.”

The Piano (1993)

Jane Campion made history as the first female filmmaker to win the coveted Palme D’Or for her evocative drama "The Piano,” starring Holly Hunter, delivering an incredible wordless performance as piano playing mute Ada was sent from Scotland to New Zealand for an arranged marriage in the mid-19th-century wilderness. Ada finds herself drawn to earthy local George Baines (Harvey Keitel), who agrees to return her piano in exchange for intimate lessons, sparking a dangerous yet passionate bond and threatening her stable union with landowner Alistair Stewart (Sam Neill.)

The striking New Zealand scenery pops off the screen, but Hunter’s raw, vulnerable turn conveys longing, suffering, and bliss solely through expression that mesmerises. Hunter rightfully won the Best Actress Oscar in 1994, one of the film’s 3 Academy Awards, cementing The Piano’s importance as feminist cinema. While tragic and not your typical sweeping romance, the erotic connection between Ada and Baines leaves one breathless.

Muriel's Wedding (1994)

Australian export Toni Collette became an instant star with her breakout lead role in 1994’s comedy drama “Muriel’s Wedding.” She’s the ultimate ugly duckling, as is the overweight, socially awkward Muriel Heslop, who spends her time listening to ABBA and dreaming of a wedding day to lift her out of her dead end small town life, if only to prove her judgmental friends and bullies wrong.

When she unexpectedly finds herself caught up in a sham of a marriage with a handsome but troubled South African swimmer, David Van Arkle (Daniel Lapaine), who needs Australian residency, it seems her big day has shockingly arrived, even if built on lies tied to unachieved dreams of happily ever after. Muriel grows up quickly in the aftermath, realising that getting married means nothing without self-respect. With genuine mishaps and messy leads who talk over each other, "Muriel’s Wedding” rings uncomfortable true while still charming. No wonder its $15 million Australian haul made it the highest grossing Aussie film in local history at that time.

Sliding Doors (1998)

I’m a sucker for “what if” romance premises exploring the subtle branches of fate, so 1998’s "Sliding Doors,” starring Gwyneth Paltrow, captured my curiosity. Paltrow plays Helen, a woman whose life diverges onto parallel paths after whether or not she catches her train, altering her destiny. In reality, she comes home early to find her boyfriend Gerry (John Lynch) cheating on her, which devastates her self-esteem. In the other, she misses her stop, gets fired from work, but meets a charming stranger, James (John Hannah), who boosts her confidence.

Which man and scenario were Helen fated to end up with? Romantics will surely see the film as a meditation on following one’s heart. Paltrow shows emotional range, toggling between two Helens—one downtrodden and one more hopeful, thanks to James’ positive influence. We can’t help analysing our lives, tracing back singular sliding door moments that set us on a certain road after seeing Helen’s romantic fate hinge on such everyday randomness.

Clueless (1995)

Any 90s girl can quote whole scenes from Amy Heckerling’s slang-y teen classic "Clueless,” starring Alicia Silverstone as Cher, the ultimate Valley Girl with a heart of gold. Though seemingly shallow and boy crazy, Cher plays matchmaker for teachers and lonely wallflowers alike between memorable shopping sprees before realising her own feelings for her former stepbrother Josh (Paul Rudd). Silverstone became the era’s definition of a teen queen after "Clueless," with her charm and comedic flair winning over audiences.

And while fashion may change, Cher’s capacity for self-improvement while staying relentlessly true to herself remains timeless. I'll be the first to admit I gleefully watched “Clueless” upwards of 10 times in the 90s, both for the irresistible humour and costumes. But beneath the candy-colored gloss lies a winning heroine in Silverstone’s Cher and her against-the-odds romance with Josh. As if any other decade could produce such a fetch-90s film!

Four Weddings and a Funeral (1994)

Hugh Grant cemented his fame as the commitment-phobic Charles; he attends four friends' nuptials throughout the film, secretly pining for the unattainable bombshell Carrie (Andie MacDowell.) Of course, love blooms in unconventional ways when Charles connects with Carrie’s quirky American sidekick Fiona (Kristin Scott Thomas).

Directed by Mike Newell, "Four Weddings" struck a chord for capturing genuine friendship dynamics within a familiar romance construct buoyed by Grant’s signature charm and fumbling wit. With over $245 million grossed worldwide and an Oscar nomination for Best Picture, clearly, moviegoers worldwide swooned for this unconventional British rom-com. And with good reason—it stands among the best the genre has to offer from the era. Myself included, clearly!

The Wedding Singer (1998)

Adam Sandler showed his sweeter romantic comedy chops as struggling wedding singer Robbie Hart, who finds a second chance at love with charming waitress Julia (Drew Barrymore). After being left at the altar by his fiancée, Robbie descends into cynicism about love and weddings. But Julia's own engagement problems help restore his faith in romance. With big hair, bad dancing, and a true rom-com wedding dash finale set to a lively 1980s soundtrack, "The Wedding Singer" leans heavily into wedding movie tropes but is buoyed by Sandler and Barrymore's palpable chemistry.

There’s Something About Mary (1998)

The Farrelly Brothers pushed the outlandish, gross-out comedy envelope with this unlikely love story between disaster-prone Ted (Ben Stiller) and his idealised childhood crush Mary (Cameron Diaz). Years after a humiliating prom date gone awry, unlucky-in-love Ted hires sleazy private investigator Healy (Matt Dillon) to track Mary down, only to find Healy developing his own obsession with her. As each male suitor suffers painful slapstick accidents vying for Mary's affection, the film blends hilarious, raunchy comedy with an unexpectedly sweet story of never letting go of that special someone from your youth.

As Good as It Gets (1998)

Jack Nicholson scored an Oscar for disagreeable author Melvin Udall, whose life gets turned upside down when he develops an attachment to his neighbour Simon (Greg Kinnear) and local diner waitress Carol (Helen Hunt). Melvin's severe OCD makes him highly unlikeable and unable to function without his rigid routine. But Simon's brutal assault and Carol's own money problems provide an unlikely opportunity for Melvin to help others for the first time while falling for Carol. Nicholson and Hunt's chemistry brought humour and emotion to this offbeat yet charming story of an unlikeable man's late life transformation through love.

I think Melvin Udall ranks as one of my favourite film characters ever!

Romeo + Juliet (1996)

Baz Luhrmann amplified Shakespeare's star-crossed lovers tragedy into a fast-paced modern gang warfare setting in this adaptation. Leonardo DiCaprio and Claire Danes portrayed the iconic smitten teenagers from rival families, forbidden to act on their burgeoning affection. Beautifully shot with a youthful soundtrack, inventive camerawork, and colourful mise en scène, Luhrmann aimed to make The Bard feel fresh and accessible to younger audiences while retaining his signature heightened theatricality and emotional power. And wow did he ever!

10 Things I Hate About You (1999)

This beloved teen rom-com put a 90s spin on Shakespeare’s ‘Taming of the Shrew’ with Julia Stiles stunning as strong-willed feminist Kat, less than enthused when told she can’t date until her popular sister Bianca (Larisa Oleynik) does. Enter intense bad boy Patrick Verona (Heath Ledger), paid by nerdy suitor Cameron (Joseph Gordon-Levitt) to charm the sharp-tongued Kat. With clever Shakespeare Easter eggs and a slamming paintball meeting cute for the ages between Stiles and Ledger, 10 Things breathed new life into the late 90s high school film scene with its quick banter and winning cast.

City of Angels (1998)

Meg Ryan and Nicolas Cage brought tear-jerking star power to this supernatural romance about Seth, an angel who gives up immortality for emotionally complex surgeon Maggie Rice (Ryan). Drawn to experience human senses he's never felt before, Seth has never known intimacy until Maggie awakens in him new depths of love. Ryan and Cage made for a striking screen pair, while director Brad Silberling emphasised vivid Los Angeles scenery and the beauty of everyday details through new angel eyes. The iconic final scene will water the eyes of any diehard romantic.

Never Been Kissed (1999)

Drew Barrymore shines in this funny, moving teen romantic comedy as Josie Geller, a 25-year old unmarried copy editor tasked with enrolling in high school undercover for a news story. Reliving her own suppressed nerdy past, Josie finally gets to experience the teen rites of passage that eluded her before, including befriending the cool kids and catching the eye of attractive teacher Sam (Michael Vartan). Barrymore and Vartan shared palpable chemistry despite the initial odd May/December taboo setup. With hilarious narration and montages punctuating Josie’s escalating hijinks, Never Been Kissed remains a seminal high school rom-com entry.

It Could Happen to You (1994)

Directed by Andrew Bergman, starring Nicolas Cage, Bridget Fonda, and Rosie Perez. A New York City police officer (Charlie Lang) accidentally gives a waitress (Yvonne Biasi) half of his winning lottery ticket, leading to complications and questions about love, trust, and fate. This whimsical romantic comedy explored what happens when a selfless act unexpectedly links two strangers together despite differences in status, ambitions, and life circumstances.

Grosse Pointe Blank (1997)

Directed by George Armitage, starring John Cusack, Minnie Driver, and Alan Arkin. A hitman (Martin Blank) returns to his hometown of Grosse Pointe for his 10-year high school reunion and struggles to confront his mysterious past, damaged relationships, and the choices that set him on a violent career path. While more of a dark action comedy, the romance between Cusack and Driver's bantering assassin and forgiving target steals the show.

Sense and Sensibility (1995)

Directed by Ang Lee and starring Emma Thompson, Kate Winslet, Alan Rickman, and Hugh Grant, this period drama adapted the classic Jane Austen novel about two sisters moving opposite ways on the spectrum between sense and sensibility. After the death of their father, proper Elinor Dashwood (Thompson) and wildly romantic Marianne (Winslet) both experience affairs of the heart as they search for fiscal security and love. With gorgeous cinematography and top-shelf acting, Ang Lee breathed new life into Austen's examination of 19th century gender dynamics and marrying for love versus money.

The 1990s offered up some of cinema's most iconic and unforgettable movie romances that continue to charm audiences long after their release. While stories of lovers overcoming obstacles are certainly nothing new or original, the decade struck the perfect balance between escapist fantasy and emotional realism.

Supported by first-rate direction and terrific lead chemistry, these 25 romance films transport viewers effortlessly into the fictional worlds of these memorable characters. We laughed, sighed, and shed tears right alongside the couples on screen.

While societies and cultures have greatly changed since the 1990s, the longing for love and connection endures universally across all generations. These 25 time-tested romantic films speak that universal language, making them beloved classics that will never fade out of fashion when we need to be swept up in a heartfelt love story.