16 Iconic 90s Rom-Coms That Defined the Decade

The 90s brought us some of the most iconic romantic comedies that are still loved today. These films captured the magic of love, laughter, and heartwarming moments, making them perfect for anyone looking for a feel-good movie. From unexpected love stories to hilarious misunderstandings, these rom-coms have something for everyone. They also introduced us to unforgettable characters who are just as charming now as they were back then. Whether you are rewatching your favorite classic or discovering one for the first time, these films never fail to deliver.

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Pretty Woman (1990)

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Pretty Woman is one of the most beloved romantic comedies of all time. The film tells the story of Vivian Ward, a prostitute who meets a wealthy businessman, Edward Lewis. As their relationship grows, both characters experience a personal transformation. The chemistry between Julia Roberts and Richard Gere is undeniable, making this movie a true classic. Its themes of love and second chances have resonated with audiences for years, creating a legacy that has stood the test of time.

The film explores class differences, self-worth, and the complexities of relationships. Vivian’s journey from a struggling woman to someone who learns to embrace her worth is inspiring. With iconic scenes like the shopping spree and the memorable “big mistake” moment, Pretty Woman remains a staple of romantic comedy history.

Notting Hill (1999)

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Set in the charming neighborhood of Notting Hill, this rom-com brings together a famous actress and an ordinary bookseller. William Thacker, played by Hugh Grant, is surprised when the Hollywood star Anna Scott, portrayed by Julia Roberts, walks into his small bookstore. Their unlikely romance unfolds as they navigate the challenges of fame and privacy. The film is known for its witty dialogue and heartwarming moments.

Notting Hill is a perfect example of a romantic comedy that balances humor with sincerity. The chemistry between Grant and Roberts shines through, with moments of vulnerability that make their relationship feel genuine. The film’s idyllic setting and memorable lines make it a favorite for anyone who loves a feel-good story with a bit of starry-eyed fantasy.

When Harry Met Sally (1990)

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This 1990 film delves into the question of whether men and women can just be friends. Starring Billy Crystal as Harry and Meg Ryan as Sally, the movie follows their friendship as it evolves over the years. What makes this rom-com stand out is the depth of the characters and their witty banter. It shows how love can grow out of friendship, with both characters gradually realizing they are meant to be together.

The movie is best known for its clever dialogue and unforgettable scenes, especially the iconic moment at Katz’s Deli. It explores the complexities of relationships, timing, and emotional connections in a way that feels both relatable and humorous. When Harry Met Sally remains a benchmark for romantic comedies, offering insights into love and the quirks of human connection.

Sleepless in Seattle (1993)

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Sleepless in Seattle is a quintessential 90s romantic comedy that combines heart and humor. The film tells the story of Sam Baldwin, a widower who struggles to move on after the death of his wife. After sharing his story on a radio show, Sam unexpectedly captures the attention of Annie Reed, played by Meg Ryan, who is engaged to another man.

The charm of the movie lies in its exploration of fate, love, and the idea of soulmates. Tom Hanks and Meg Ryan’s performances are endearing, with their natural chemistry making the film memorable. Sleepless in Seattle continues to be a go-to rom-com for anyone who believes in love at first sight and the idea that sometimes, destiny has a hand in romance.

10 Things I Hate About You (1999)

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A modern take on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You stars Heath Ledger and Julia Stiles in a story set in a high school. The film focuses on the relationship between Patrick Verona, the rebellious outsider, and Kat Stratford, a strong-willed and independent young woman. Patrick is hired to date Kat, who has a strict father who forbids her from seeing boys unless her younger sister, Bianca, dates too.

This 90s classic is loved for its humor, memorable quotes, and the strong performances of its cast. Ledger’s portrayal of Patrick made him an icon of the decade, while Stiles’ witty and intelligent Kat became a role model for young women. The film skillfully blends romance with sharp humor, and its heartwarming finale continues to capture the essence of teenage love.

My Best Friend’s Wedding (1997)

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In My Best Friend’s Wedding, Julia Roberts stars as Julianne Potter, a woman who realizes she is in love with her best friend, Michael, just as he announces his engagement to someone else. Julianne tries to sabotage the wedding to win him over, but as the story progresses, she learns some valuable lessons about love, friendship, and self-respect.

This film stands out for its comedic yet bittersweet portrayal of unrequited love. The chemistry between Roberts and Dermot Mulroney (who plays Michael) adds to the tension and emotional depth of the story. My Best Friend’s Wedding is filled with memorable moments and poignant insights into what it means to love and let go.

You’ve Got Mail (1998)

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You’ve Got Mail reunites Tom Hanks and Meg Ryan, this time playing two rival bookstore owners who fall in love through anonymous email exchanges. Their online relationship develops while they unknowingly continue to bicker in person, unaware of their connection. The film is a delightful mix of technology, love, and New York City charm.

The movie’s appeal lies in its relatable themes of loneliness and the search for true love. It also offers a glimpse into the early days of the internet and online dating. Hanks and Ryan bring their usual chemistry to the film, making it a heartwarming, fun watch that perfectly captures the excitement and uncertainties of falling in love in the digital age.

While You Were Sleeping (1995)

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In While You Were Sleeping, Sandra Bullock stars as Lucy, a lonely ticket agent who saves the life of a man named Peter, only to find herself caught in a misunderstanding when he falls into a coma. While Peter’s family believes that they are a couple, Lucy starts to form real connections with his family, especially with his brother, Jack, played by Bill Pullman.

The film mixes humor with heartfelt moments, with Bullock’s performance shining as a woman who learns to find her voice and embrace love. The themes of family, mistaken identity, and self-discovery make this rom-com a timeless favorite. While You Were Sleeping is filled with warm moments and a sweet, satisfying ending that resonates long after the credits roll.

Runaway Bride (1999)

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Runaway Bride reunites Julia Roberts and Richard Gere in a story about a woman who has left multiple fiancés at the altar. As a reporter named Ike Graham is sent to write about her, he starts to uncover the truth about her fears and past. Over time, Ike and Maggie’s relationship grows, as they both learn more about themselves and each other.

The film combines humor, romance, and personal growth, with Roberts and Gere’s chemistry making it a compelling story about love and commitment. Maggie’s journey of finding herself and realizing what she truly wants in a partner resonates with many viewers. Runaway Bride is a charming, feel-good film that explores the importance of being true to oneself in love.

Fools Rush In (1997)

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Fools Rush In tells the story of a free-spirited woman, Isabel, and a more conservative man, Alex, who meet unexpectedly and quickly fall in love. After a whirlwind romance, the two face challenges that come with their cultural differences, family expectations, and differing views on life.

Salma Hayek and Matthew Perry lead the cast with great chemistry, portraying a couple who learn the importance of compromise and understanding in a relationship. The film is filled with humorous moments and touching insights about love, identity, and the challenges of making a relationship work. Fools Rush In reminds us that love, though unpredictable, is worth fighting for.

The Truth About Cats and Dogs (1996)

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This romantic comedy explores the idea of identity and self-perception. Janeane Garofalo stars as Abby, a radio talk show host who gives relationship advice while struggling with her own insecurities. When a listener falls in love with Abby’s voice, she enlists the help of her beautiful but self-conscious friend, Noelle, played by Uma Thurman.

The film is unique in its approach, offering a mix of humor and romance with a focus on how we see ourselves and how others perceive us. Garofalo’s portrayal of Abby is relatable and grounded, and the film touches on themes of authenticity and love. The Truth About Cats and Dogs is a charming reminder that beauty comes in many forms, and love can flourish in unexpected ways.

Something’s Gotta Give (1993)

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In this rom-com, Jack Nicholson plays a wealthy playboy who finds himself falling for Diane Keaton, a woman many years his senior. As their relationship develops, both characters are forced to confront their beliefs about love, aging, and personal fulfillment.

The film shines due to its stellar cast and the way it portrays mature love. Nicholson and Keaton’s performances are both funny and touching, offering a refreshing take on romance. Something’s Gotta Give stands out for addressing age and the possibility of finding love later in life.

Maid in Manhattan (2002)

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Although released in the early 2000s, Maid in Manhattan has a 90s feel due to its romantic comedy style. Jennifer Lopez plays Marisa, a hotel maid who is mistaken for a wealthy socialite by a senator’s son, played by Ralph Fiennes. As their relationship blossoms, Marisa must navigate the challenges of her double life.

The film is a modern Cinderella story with themes of class and identity. Lopez and Fiennes create a compelling on-screen relationship, with moments of humor and romance. Maid in Manhattan is a charming film about love, ambition, and the secrets we keep to protect our hearts.

Chasing Liberty (2004)

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This film offers a fresh take on the rom-com genre with a young Mandy Moore playing the president’s daughter, who is determined to live life outside the confines of her royal status. When she goes on a spontaneous trip to Europe, she meets a charming stranger, played by Matthew Goode, who turns out to be assigned to protect her.

The story is light-hearted and adventurous, with romantic moments that develop naturally between Moore and Goode’s characters. Chasing Liberty is a fun escape into the world of young love, self-discovery, and taking chances. The film highlights the importance of living authentically and following your heart.

The Wedding Planner (2001)

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Jennifer Lopez stars as a wedding planner who falls for the groom of one of her clients, played by Matthew McConaughey. The film explores the complexities of love, ethics, and following one’s desires in the face of responsibility.

Lopez and McConaughey’s chemistry adds depth to the story, making it a delightful watch. The film is lighthearted yet emotional, with relatable moments about choosing love over duty. The Wedding Planner has become a classic rom-com for anyone who believes that true love is worth pursuing, even when it seems impossible.

Serendipity (2001)

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Though released in the early 2000s, Serendipity has a classic 90s rom-com feel with its charming, fate-driven plot. John Cusack and Kate Beckinsale star as Jonathan and Sara, two people who meet by chance and form an instant connection. However, they part ways, believing that fate will bring them back together.

This film explores the idea of destiny and how love can be found in unexpected places. Cusack and Beckinsale bring great warmth and charm to the film, making it a heartwarming journey of love and hope. Serendipity reminds viewers that sometimes love just happens when you least expect it.

This article originally appeared on Avocadu.