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While there have been plenty of memorable eras for the romance genre in film, the 1990s were undoubtedly a golden one. Romances like Titanic and Shakespeare in Love offer audiences everything ranging from heart-wrenching dramas to feel-good love stories that still have viewers bawling and swooning today. Whether it was the palpable chemistry between the leads or the tales of passion that defy the odds, these ’90s romance classics have left a strong imprint on film history.
To celebrate the greatness of such a decade, this list will look back at some of the most defining, best romance movies of the 1990s that not only entertained but also influenced the way we perceive love these days. We rank them by their memorability, enduring impact, and the way they continue to inspire new generations of romantics and filmmakers alike.
10
‘Shakespeare in Love’ (1998)
Directed by John Madden
John Madden‘s celebration of love is a whimsical romance that blends history and fiction with a romantic twist. Set in 1593 London, Shakespeare in Love follows William Shakespeare (Joseph Fiennes), who suffers from writer’s block until he meets Viola de Lesseps (Gwyneth Paltrow), a noblewoman disguising herself as a man to act on stage. Inspired by her, Shakespeare transforms his play into “Romeo and Juliet,” while they embark on a secret affair.
While many agree that Shakespeare in Love wasn’t worthy of the Best Picture Academy Award, the film’s influence can’t be denied. It was groundbreaking for several reasons, starting with its clever promo that blended traditional movie marketing with unconventional strategies and its campaign for awards season, where it was carefully positioned as a front-runner for multiple Oscars. With a clever script by Marc Norman and Tom Stoppard, this cinematic gem is one of the most influential and emblematic films of the 1990s, particularly in the romance genre. Its vibrant performances, stunning costumes, and the chemistry between Paltrow and Fiennes are standouts.
9
‘Four Weddings and a Funeral’ (1994)
Directed by Mike Newell
Four Weddings and a Funeral redefined the genre with its captivating blend of wit, warmth, and heartfelt moments. The movie follows Charles (Hugh Grant), a charming but commitment-averse bachelor, as he navigates love and friendship through a series of weddings and funerals. While he ends up falling for Carrie (Andie MacDowell), their romance is complicated by her engagement and his fears of commitment.
Featuring a poignant exploration of love and loss, Four Weddings and a Funeral is a quintessential 20th-century romantic comedy that defined the genre, earning Oscar nods for Best Picture and Best Original Screenplay. Additionally, the witty Mike Newell boasts plenty of memorable characters, standout performances, and amazing lead chemistry, setting a new standard for British cinema and elevating Grant to superstardom in the meantime.
8
‘You’ve Got Mail’ (1998)
Directed by Nora Ephron
With a perfect blend of nostalgia, humor, and a touch of old-school romance in contemporary surroundings, Nora Ephron‘s pioneering, tech-savvy, digital-age film still has a timeless feel despite its late ’90s setting. The film follows Tom Hanks and Meg Ryan as two business rivals who unknowingly fall in love online while exchanging witty emails.
For those who enjoy lighthearted comedies that still pack some emotional moments, You’ve Got Mail is one of the top ’90s romantic films. With Ephron’s signature script, this engrossing film captures the magic of falling in love — online and offline — in a way that feels fresh and entertaining. In addition to the charming chemistry between Hanks and Ryan and their captivating dynamic, You’ve Got Mail is a beautiful exploration of how love can blossom in the most unexpected ways — and with the last person you’d ever expect.
7
‘Romeo + Juliet’ (1996)
Directed by Baz Luhrmann
Baz Luhrmann‘s Romeo + Juliet has rapidly established itself as one of the most iconic romance films of the decade. This modern adaptation of Shakespeare’s classic tale is set in a vibrant, crime-ridden Verona Beach, where two star-crossed but ill-fated lovers (Leonardo DiCaprio and Claire Danes) fall deeply in love amidst a backdrop of gang violence.
Anchored by Luhrmann’s bold artistic vision and the amazing central performances, this beloved box-office hit combines Shakespearean dialogue with a stunning modern aesthetic, visually striking shots, and raw emotion and chemistry between the two leads that perfectly capture the intensity of true love. Despite mixed reviews at the time of its release, Romeo + Juliet has established itself as a pop culture icon, continuing to influence film adaptations of classic literature.
6
‘Chungking Express’ (1994)
Directed by Wong Kar-Wai
Wong Kar-Wai‘s romantic masterwork remains one of the filmmaker’s most romantic movies and is a defining international film of the 1990s. The film follows two melancholic Hong Kong policemen who fall in love with two women: one a female underworld figure, the other a beautiful waitress at the light-night restaurant he frequents.
The hopeless romantics fascinated by interconnected stories within the same narrative will find Chungking Express a captivating watch, as it offers not one but two wonderful stories of longing and yearning in the bustling streets of Hong Kong, with visually stunning cinematography and an atmospheric soundtrack that further emphasizes its dreaminess. Celebrated for its artistic vision and for capturing the essence of the decade in the city, Wong Kar-Wai’s film has easily become one of the most memorable in the genre, delivering a thoughtful message about the passage of time and unfulfilled desires.
5
‘Sleepless in Seattle’ (1993)
Directed by Nora Ephron
Also directed by Ephron and starring the ever-charming duo Tom Hanks and Meg Ryan, Sleepless in Seattle tells the story of Sam Baldwin (Hanks), a widower who moves to Seattle with his son, Jonah (Ross Malinger), after his wife’s passing. On Christmas Eve, Jonah calls a national radio talk show, encouraging his father to share his story of love and loss. Among the many listeners captivated by his story is Annie (Ryan), an unhappily engaged reporter who becomes fascinated by the idea of fate bringing two people together.
Widely acclaimed for its unique approach to the romantic comedy genre, Sleepless in Seattle pays homage to An Affair to Remember, using it as a plot device to explore similar themes and offering a fresh take on love and relationships through its memorable characters. Unlike typical romantic comedies, it keeps the leads apart for most of the story, relying on fate and serendipity to bring them together. With beautiful cinematography that creates two distinct worlds for its characters, Sleepless in Seattle has become a fan-favorite in the genre and is surely one of the best ’90s romance movies.
4
‘Pretty Woman’ (1990)
Directed by Garry Marshall
This turn-of-the-decade comedy by Garry Marshall tells the story of Vivian Ward (Julia Roberts), a young sex worker who captures the heart of wealthy businessman Edward Lewis (Richard Gere) after he hires her for a week. While the arrangement is purely transactional at the beginning, the two ultimately develop genuine feelings for each other.
Although it received mixed reviews from critics due to its portrayal of sex work, Pretty Woman is undeniably one of the most memorable romance features of the 1990s, influencing movies even today, such as Sean Baker‘s divisive Best Picture winner Anora. Elevated by the palpable connection between the two leads and performances, Pretty Woman is a quintessential 1990s romantic comedy that packs iconic fashion moments, an unforgettable soundtrack, and an enduring influence on pop culture.
3
’10 Things I Hate About You’ (1999)
Directed by Gil Junger
This modern adaptation of William Shakespeare’s The Taming of the Shrew transports the story to a late-1990s American high school. Cameron (Joseph Gordon-Levitt) is smitten with Bianca (Larisa Oleynik), but there’s a catch — her strict father has a rule: Bianca cannot date until her older sister, the sharp-tongued and independent Kat (Julia Stiles), finds a boyfriend too. Determined to make it work, Cameron pays bad boy Patrick (Heath Ledger) to charm Kat.
Gil Junger‘s unconventional Shakespeare re-telling brings a timeless classic into a contemporary setting, making it a relatable and engaging tale for a younger audience while also appealing to adults thanks to its sharp wit, standout performances, and clever script. Exploring themes of identity, family dynamics, and first love, 10 Things I Hate About You is packed with iconic moments, beloved characters, and an utterly engaging romance story that enemies-to-lovers enthusiasts will love.
2
‘Before Sunrise’ (1995)
Directed by Richard Linklater
Richard Linklater‘s Before Sunrise is a beautiful and contemplative romantic drama that explores the magic of human relationships. Starring Ethan Hawke and Julie Delpy in two memorable performances, the slice-of-life feature follows the two strangers as they meet on a train and impulsively decide to spend a night wandering through Vienna, engaging in deep conversations about life, making memories, and developing a strong bond.
With a flawless 100% Rotten Tomatoes rating, Linklater’s movie has often been praised for its profound dialogue, natural performance, and refreshingly realistic, romantic portrayal of modern love. With minimalistic storytelling at its center that presents a bittersweet perspective on relationships, Before Sunrise delves into themes of self-discovery, mortality, and the unquenchable search for meaning, making it more than a simple romance. At its core, it is a poignant reflection of the transient nature of human connection, capturing the quiet beauty of two people sharing a profound bond that lingers long after the credits roll.
Before Sunrise
- Release Date
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January 27, 1995
- Runtime
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101 minutes
- Director
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Richard Linklater
1
‘Titanic’ (1997)
Directed by James Cameron
Based on the real-life sinking of the RMS Titanic in 1912, James Cameron‘s epic romance tale is framed by an elderly Rose DeWitt Bukater Calvert (Gloria Stuart) recounting her experiences aboard the ship. The film takes us back to her younger years, following the character (Kate Winslet) who falls in love with a penniless artist (Leonardo DiCaprio), despite their social differences and the fact that she is trapped in an unhappy relationship on the ill-fated Titanic.
Titanic has received mixed feedback — some critics praise its technical achievements and dramatic story, and others find the dialogue and romance cliché. Still, Cameron’s movie is the kind of film that refuses to sink (pun intended) into obscurity. With its meticulous, jaw-dropping set design and a score by James Horner that tugs at your heartstrings, Titanic is often hailed as a masterpiece of innovation and sweeping emotion that still has viewers swooning to this day.
