10 Romance Movies From The 1990s That Were Ahead Of Their Time

Romance movies say a lot about the contemporary cultural mindsets of the time they were made, and the 1990s are no exception. Filmmaking and moviegoing were changing during this pivotal decade, and many topics that were considered taboo were brought to the forefront of cinema because society was becoming ready for more subversive and experimental movies. Whether this was expressed through style or subject matter, the way these films approached storytelling holds up well when compared to modern works. Many of the filmmakers behind these projects have gone on to help transform cinema.

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The 1990s are often considered a large part of the Golden Age of rom-coms, but many of the most revolutionary pieces of cinema from the decade brilliantly blend genres. Though there are many great rom-coms from the ’90s that are better remembered, they’re of their time and adhere to the formulas and archetypes that were popular at the time. While there’s nothing wrong with this, it doesn’t push boundaries in the way that these films did, taking risks that often didn’t make them the most commercially successful but have preserved their legacy into the present day.

10 How Stella Got Her Groove Back (1998)

Directed by Kevin Rodney Sullivan

How Stella Got Her Groove Back RRomanceComedyDrama

How Stella Got Her Groove Back follows Stella Payne, a successful stockbroker, as she takes a vacation to Jamaica to unwind from her demanding career. While there, she meets a charismatic young man named Winston and begins to rediscover her passions and zest for life. Directed by Kevin Rodney Sullivan, the film stars Angela Bassett and Taye Diggs, exploring themes of love, rejuvenation, and self-discovery.

Director Kevin Rodney Sullivan Release Date August 14, 1998 Writers Terry McMillan , Ronald Bass Cast Angela Bassett , Taye Diggs , Whoopi Goldberg , Regina King , Suzzanne Douglas , Michael J. Pagan , Sicily Johnson , Richard Lawson

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Age-gap relationships have long been a part of cinema history, but most of the romances depicted onscreen show an older man getting involved with a younger woman. However, How Stella Got Her Groove Back flips the script and sees Stella (Angela Bassett) open herself up to love and new experiences when she meets the younger Winston (Taye Diggs). Though it hits many of the same beats as traditional rom-coms, How Stella Got Her Groove Back shouldn’t be overlooked for its contributions to the genre.

Romance movies have always been a safe and important place for female desire and sexuality to be explored onscreen, as most other genres have historically catered to the male gaze.

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Romance movies have always been a safe and important place for female desire and sexuality to be explored onscreen, as most other genres have historically catered to the male gaze. How Stella Got Her Groove Back and contemporary movies like The Idea of Youcenter on the pleasure of an older woman and see her rediscover and reclaim her sexuality through the characters taking their lives into their own hands. The fact that How Stella Got Her Groove Back was already tackling this issue in the late ’90s is incredible.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
How Stella Got Her Groove Back (1998)	50%	66%

9 Muriel’s Wedding (1994)

Directed by P.J. Hogan

Muriel’s Wedding (1994) RComedyDramaRomance

Muriel’s Wedding is a 1994 Australian comedy-drama directed by P.J. Hogan. The film stars Toni Collette as Muriel Heslop, a socially awkward woman who dreams of escaping her miserable existence in the small town of Porpoise Spit by getting married. With the help of her friend Rhonda, Muriel embarks on a journey of self-discovery, learning to define her own happiness beyond societal expectations.

Director P.J. Hogan Release Date March 31, 1995 Writers P.J. Hogan Cast Sophie Lee , Roz Hammond , Toni Collette , Belinda Jarrett , Pippa Grandison , Bill Hunter , Jeanie Drynan , Dan Wyllie , Gabby Millgate , Gennie Nevinson , Rachel Griffiths , Matt Day , Chris Haywood , Daniel Lapaine , Susan Prior , Nathan Kaye , Cecily Polson , Rob Steele , Geneviève Picot , Richard Sutherland , Steve Smith , Katie Saunders , Dene Kermond , Jeamin Lee , Jon-Claire Lee , Kuni Hashimoto , Ken Senga , Des Rodgers , Rohan Jones Runtime 106 Minutes Expand
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Starring the incomparable Toni Collette, Muriel’s Wedding is a cult classic Australian romantic dramedy from 1994 about Muriel (Collette), a girl desperate for love and acceptance. Though Muriel’s Wedding is full of humor and over-the-top characters, it has dramatic moments, and the story forces Muriel to grapple with her choices and the price she’ll pay for attention and the facade of a perfect wedding and marriage. In reality, it’s the friendship between Muriel and her friend Rhonda (Rachel Griffiths) that’s the true love story.

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The director, P.J. Hogan, would go on to direct My Best Friend’s Wedding, one of the most famous rom-coms of the ’90s, but his later work wasn’t as groundbreaking as Muriel’s Wedding. Well aware of the pitfalls of the rom-com genre and its notoriously down-on-their-luck heroines, Muriel’s Wedding makes Muriel as awkward as she is charming and encourages the audience to put their faith in her. While the performances are what make the film, the seamless blend of genres and affecting story are what make Muriel’s Wedding a classic.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Muriel’s Wedding (1994)	81%	84%

8 The Incredibly True Adventure Of Two Girls In Love (1995)

Directed by Maria Maggenti

The Incredibly True Adventure of Two Girls in Love ComedyDramaRomance

The Incredibly True Adventure of Two Girls in Love is a romantic drama that explores the relationship between two teenage girls from divergent social and economic backgrounds. Released in 1995, it showcases their journey and the challenges they face while navigating a burgeoning romance.

Director Maria Maggenti Release Date June 16, 1995 Cast Laurel Holloman , Nicole Ari Parker , Maggie Moore , Kate Stafford , Toby Poser , Stephanie Berry , Dale Dickey , Nelson Edwin Rodríguez , John Elsen , Katlin Tyler , Anna Padgett , Chelsea Catthouse , Andrew Wright , Babs Davy , Lillian Kiesler , Maryette Charlton Runtime 94 minutes Expand

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The Incredibly True Adventure of Two Girls in Love isn’t just an important piece of filmmaking because it follows the development of an LGBTQ+ relationship between two young women, but because it’s a stellar movie. Randy (Laurel Holloman) and Evie (Nicole Ari Parker) have different struggles and backgrounds. However, they’re brought together by their feelings of ostracization from their small town and their budding feelings for each other. As much a coming-of-age movie as it is a romance, The Incredibly True Adventure of Two Girls in Love features neither a tragic nor entirely happy ending.

Fortunately, Randy and Evie get a fair chance to explore their love, and the film takes on their growing feelings with kindness.

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The other characters are far from all accepting and understanding of Randy and Evie’s relationship. However, the film indicates that the pair intend to hold onto their connection and each other. This differs from the many unhappy endings that LGBTQ+ films featured during this time, which often painted queer relationships as only ending in heartbreak. Fortunately, Randy and Evie get a fair chance to explore their love, and the film takes on their growing feelings with kindness.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
The Incredibly True Adventure of Two Girls in Love (1995)	80%	69%

Related 10 Underrated LGBTQ+ Coming-Of-Age Movies

Coming-of-age movies give insight into the hardships and pitfalls of growing up and having that representation for LGBTQ+ youth is very important.

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7 The Watermelon Woman (1996)

Directed by Cheryl Dunye

The Watermelon Woman ComedyDramaRomance

The Watermelon Woman is a pioneering film from 1997 directed by Cheryl Dunye. This mockumentary follows Cheryl, a young Black filmmaker investigating the life of a 1930s Black actress known only as “The Watermelon Woman.” Through her journey, Cheryl explores themes of racial and sexual identity, blending documentary and narrative styles in a deeply personal exploration of history and representation.

Director Cheryl Dunye Release Date March 5, 1997 Studio(s) Dancing Girl Writers Cheryl Dunye Cast Cheryl Dunye , Guinevere Turner , Camille Paglia , Valarie Walker , Lisa Marie Bronson Runtime 90 Minutes Expand

Cheryl Dunye’s landmark movie, The Watermelon Woman, was written, directed, and stars Dunye, making it a true piece of independent auteur cinema. The Watermelon Woman was the first feature film directed by an out Black lesbian woman, Dunye, and is considered one of the most important works of the New Queer Cinema movement of the 1990s. This movement was critical in bringing LGBTQ+ voices into the mainstream of filmmaking, and Dunye pushed boundaries even further by interrogating the intersection between sexuality, race, and gender in cinema.

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However, the structure and style of The Watermelon Woman were also heavily influential in its combination of documentary-like footage and Dunye’s invention of the titular Watermelon Woman. She is a composite of the many Black actors who were overlooked during filmmaking’s early age and is important to Cheryl, who explores the Watermelon Woman’s past to inform her own take on movies. Cheryl also discovers the Watermelon Woman, who she learns was really a woman named Fae, was a lesbian herself, which allows Cheryl to look critically at her own budding relationship.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
The Watermelon Woman (1996)	92%	56%

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6 Mississippi Masala (1991)

Directed by Mira Nair

Mississippi Masala RDramaRomance

Mississippi Masala is a romantic drama directed by Mira Nair that explores cultural diversity and identity. The film follows the lives of an Indian family expelled from Uganda, relocating to Mississippi, where their daughter, Mina (Sarita Choudhury), falls in love with Demetrius (Denzel Washington), an African American man. The narrative delves into the complexities of interracial relationships and the challenges faced by immigrants in a racially segregated environment.

Director Mira Nair Release Date February 5, 1992 Writers Sooni Taraporevala Cast Denzel Washington , Sarita Choudhury , Roshan Seth , Sharmila Tagore , Charles S. Dutton , Joe Seneca , Ranjit Chowdhry , Mohan Gokhale , Mohan Agashe , Tico Wells , Yvette Hawkins , Aanjjan Srivastav , Konga Mbandu , Sahira Nair , Dipti Suthar , Varsha Thaker , Ashok Lath , Natalie Oliver , Karen Pinkston , Willy Cobs , Mira Nair , Rajika Puri , Sharon Williams , Cyreio Hughes , Stacy Swinford , Rick Senn , Jim Haffey Runtime 118 Minutes Expand

One of the most rewatchable Denzel Washington movies, Mississippi Masala, explores facets of race, class, and family obligation through the gorgeous love story of Demetrius (Washington) and Mina (Sarita Choudhury). Seeing interracial relationships onscreen is a hugely important part of what romance movies can do. Mississippi Masala explores cultural differences and expectations realistically and with nuance and empathy for the intensity and experience of immigration and racism in the United States. However, like all great romances, Mina and Demetrius don’t let their different worlds keep them apart.

Mina’s parents have trouble adapting to life in the U.S. and miss their home in Uganda, which influences their decisions.

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The chemistry between Washington and Choudhury explodes off the screen, making a compelling case for how underrated Washington is as a romantic lead. However, the lovers aren’t the only well-developed characters in the movie. Mina’s parents have trouble adapting to life in the U.S. and miss their home in Uganda, which influences their decisions. Additionally, it’s always exciting to watch a film written and directed by female filmmakers, with Sooni Taraporevala behind the script and Mira Nair as the director.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Mississippi Masala (1991)	92%	64%

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5 Metropolitan (1990)

Directed by Whit Stillman

Whit Stillman is best known for his loose trilogy about the wealthy elite class of young people in the 1980s, beginning with Metropolitan in 1990. Followed by Barcelona and The Last Days of Disco, each film explores different parts of the ’80s but are retrospective explorations of this era, as Stillman made them in the ’90s. Today, satirical and withering commentaries on the rich and their privilege are well-trodden topics in film. However, Metropolitan manages to communicate this distaste while also having empathy for its characters.

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The viewer enters the world of wealthy college students and their lives in New York City through the lens of the middle-class Tom (Edward Clements), who finds himself equally repelled by and enthralled by their world. It’s easy for the audience to share these feelings as the characters are charming and inviting, their world full of pleasure and connections. However, they’re also unafraid to hurt and manipulate others for their own ends. This dichotomy exemplifies what makes Metropolitan special. It’s a class commentary that translates to today while being rooted in its era.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Metropolitan (1990)	93%	84%

4 Before Sunrise (1995)

Directed by Richard Linklater

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10/10 Before Sunrise RDramaRomance

Two strangers, Jesse and Céline, meet on a train and decide to spend an evening together exploring Vienna. As they wander the city, they share deep conversations, form a profound connection, and experience a fleeting, yet meaningful romance, knowing their time together will end at sunrise.

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*Availability in US Director Richard Linklater Release Date January 27, 1995 Writers Richard Linklater , Kim Krizan Cast Ethan Hawke , Julie Delpy , Andrea Eckert , Hanno Pöschl , Karl Bruckschwaiger , Tex Rubinowitz Runtime 101 minutes

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Richard Linklater’s best work as a filmmaker is arguably the Before Trilogy, the seminal romantic works that explore the lifelong romance between Jesse (Ethan Hawke) and Céline (Julie Delpy). Hawke and Delpy were instrumental in the development of the characters and their dialogue in the later movies, but in the first movie, Before Sunrise, the actors are still figuring out Jesse and Céline and what they mean to each other. The stream-of-consciousness conversation between Jesse and Céline that encompasses the story is unlike other plot-driven narratives of the time.

Even though the audience spends only a day and night with Jesse and Céline, their connection is potent and immediate, and their goodbye is heartbreaking.

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However, this character-driven style and the depths that Before Sunrise goes to in exploring philosophical questions about love and modern life have been imitated time and again in cinema. Even though the audience spends only a day and night with Jesse and Céline, their connection is potent and immediate, and their goodbye is heartbreaking. Additionally, the next installments are filmed nine years apart and touch upon different stages of life, demonstrating how time can be used as a critical element of filmmaking.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Before Sunrise (1995)	100%	93%

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Related 10 Romance Movies With The Most Convincing Love Chemistry

While the plot of a romance movie drives the story forward, it’s the chemistry between actors that audiences will remember for years to come.

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3 But I’m A Cheerleader (1999)

Directed by Jamie Babbit

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10/10 But I’m A Cheerleader RComedyDramaRomance

But I’m a Cheerleader follows Megan, an all-American high school cheerleader, who is sent to a conversion therapy camp by her conservative parents after they suspect her of being a lesbian. The film explores her experiences at the camp as she navigates her identity and relationships.

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*Availability in US Director Jamie Babbit Release Date July 7, 2000 Writers Brian Peterson , Jamie Babbit Cast Natasha Lyonne , Clea DuVall , Cathy Moriarty , RuPaul , Melanie Lynskey , Katharine Towne , Katrina Phillips , Joel Michaely , Douglas Spain , Kip Pardue , Eddie Cibrian , Michelle Williams , Brandt Wille , Bud Cort , Mink Stole , Katie Donahue , Danielle Reneau , Dante Basco , Kyle Thatcher , Robert Pine , Rachelle Carson , Wesley Mann , Richard Moll , Julie Delpy Runtime 85 Minutes Expand

Hilarious, campy, but deeply emotionally resonant, But I’m A Cheerleader has become one of the most enduring cult classics from the late ’90s. The film is a satirical takedown of gender roles and homophobia that is anchored by the sweet and sensitive performances of Natasha Lyonne and Clea DuVall as Megan and Graham, the young women who find love at a conversion camp. Touching upon Megan’s journey to self-acceptance and her realization that her sexual identity is something to be celebrated, But I’m A Cheerleader was celebrated by LGBTQ+ and arthouse audiences.

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Though the initial critical reception of the movie was mixed, But I’m A Cheerleader has found its place within the romance canon and is an important addition to LGBTQ+ film history. While the story and progressive themes of the movie are highlights, the look of the sets, costumes, and world all contribute to the film’s unique appeal. Utilizing bright colors and almost storybook-esque imagery, But I’m A Cheerleader is enhanced by its over-the-top style, standing apart from the overt realism of its contemporaries.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
But I’m A Cheerleader (1999)	43%	75%

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2 Chungking Express (1994)

Directed by Wong Kar-wai

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10/10 Chungking Express (1994) PG-13DramaRomanceComedy

Chungking Express, directed by Wong Kar-wai, is a film about urban alienation and fleeting romantic connections in Hong Kong. Chungking Express explores the lives of two lovelorn police officers, each struggling to get over past relationships.

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*Availability in US Director Wong Kar-wai Release Date March 8, 1994 Studio(s) Jet Tone Films Writers Wong Kar-wai Cast Brigitte Lin , Takeshi Kaneshiro , Faye Wong , Tony Leung Chiu-wai Runtime 103 minutes Expand

It’s difficult to choose just one film by Wong Kar-wai to include, as many of his romantic and revolutionary dramas were made in the 1990s. While Happy Together and Fallen Angels incorporate the atmospheric and visual elements that Wong is known for, Chungking Express delivers all of this and more. Split into two stories in an anthology format, Chungking Express is a love story between people. Chungking Express is also in love with the medium of film itself and is often described as a movie for cinephiles.

The surrealist visuals and meandering nature of the story take their time, but in doing so, it creates an emotional impact that would touch any viewer.

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However, regarding the movie as a project that can only be enjoyed by frequent movie-goers is a mistake. The surrealist visuals and meandering nature of the story take their time, but in doing so, it creates an emotional impact that would touch any viewer. Tony Leung Chiu-wai, one of Wong’s frequent collaborators, appears in the film and gives one of his best performances as one of the police officers. Faye Wong plays opposite Leung in their section of the story, with Takeshi Kaneshiro and Brigitte Lin anchoring the first portion of the movie.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Chungking Express (1994)	88%	93%

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1 Rushmore (1998)

Directed by Wes Anderson

Rushmore RComedyDrama

Rushmore is a comedy-drama directed by Wes Anderson, featuring Jason Schwartzman in his debut role as Max Fischer, an eccentric and ambitious teenage student at Rushmore Academy. The film also stars Bill Murray as Herman Blume, a disillusioned industrialist who forms an unlikely friendship with Max, helping to guide him back on the academic road after Max’s extracurricular activities put him on the path of expulsion.

Director Wes Anderson Release Date December 11, 1998 Studio(s) American Empirical Pictures Writers Wes Anderson , Owen Wilson Cast Jason Schwartzman , Bill Murray , Olivia Williams , Seymour Cassel , Brian Cox , Mason Gamble , Sara Tanaka Runtime 93 minutes Expand

One of Wes Anderson’s earlier films remains one of his best and most emotionally arresting, as Rushmore taps into not just romantic love but the journey to loving oneself and building a community. While Max (Jason Schwartzman) spends the movie in love with Rosemary (Olivia Williams), his most significant relationship is his friendship with Herman (Bill Murray), who ends up in love with Rosemary himself. Rushmore sees Anderson pushing even further into his quirky, off-beat style and exploring love more deeply.

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Both the visual style and writing in Rushmore have been cited in discussions about the film’s legacy and influence, as it took adolescence and young love more seriously than other works of romance. Additionally, Max is not always the most likable character, as he makes many selfish decisions throughout the story before ultimately redeeming himself. However, the layered characterization is what makes the movie amazing, along with the project’s aesthetics, which proved that Anderson was doing things differently than other filmmakers.

Title	Rotten Tomatoes Critic Score	See more : All 3 Paddington Movies, Ranked From Worst To Best Rotten Tomatoes Audience Score
Rushmore (1998)	90%	91%

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