10 Timeless ’90s Romantic Comedies That Still Make Us Laugh

The 1990s marked a distinct era for romantic comedies, characterized by iconic fashion trends, memorable quotes, and cultural references that may feel outdated today. Nevertheless, these films have proven to be significantly rewatchable, captivating audiences anew with their charm and humor. The decade consistently delivered romantic comedies, each showcasing grand gestures of love and featuring some of the biggest stars of the time, factors that enhance the enjoyment of revisiting these classics. As the sub-genre has evolved, modern rom-coms have started to embrace a broader diversity of characters and narratives, yet the essence of the ’90s remains irresistible.

Interestingly, some films from this era ventured beyond traditional storytelling. Notable entries like Ang Lee’s The Wedding Banquet and Theodore Witcher’s Love Jones offer refreshing perspectives on love that, while overlooked in mainstream discussions, significantly contribute to their enduring appeal. Moreover, the traditional tropes and even the more clichéd romantic moments of ’90s cinema have a nostalgic pull, drawing audiences back for repeated viewings. Regardless of some elements feeling outdated, many of these romantic comedies improve in charm with each rewatch.

10 Only You (1994)

Directed by Norman Jewison

Robert Downey Jr.and Marisa Tomei look into one another's eyes romantically.

Upon its mid-’90s release, Only You garnered mixed reviews from critics. However, the enchanting film features Robert Downey Jr.in a rare romantic role alongside an impressive performance by Marisa Tomei. The plot revolves around Tomei’s character, Faith, who has believed since childhood that she is destined to marry a man named “Damon Bradley.” Following this belief, Faith learns that “Damon Bradley”is in Italy and embarks on a journey to find him. While her adventure doesn’t unfold as expected, she ultimately finds her own happy ending, making the film a delightful rediscovery.

9 Never Been Kissed (1999)

Directed by Raja Gosnell

Josie (Drew Barrymore) and Sam (Michael Vartan) dancing at prom in Never Been Kissed.

Despite its implausible storyline, Never Been Kissed remains a beloved favorite largely due to Drew Barrymore’s infectious performance. She portrays Josie Geller, a reporter sent undercover to a high school, where she seizes the opportunity to reinvent her teenage self.Josie’s journey resonates with many viewers, as it reflects a search for connection and acceptance. With support from a talented cast including David Arquette and Molly Shannon, Barrymore’s whimsical portrayal plays a significant role in the film’s cult status, further solidified by her recent revival of the character on her talk show.

8 It Could Happen To You (1994)

Directed by Andrew Bergman

Nicolas Cage and Bridget Fonda in a diner in It Could Happen to You

Inspired by true events, It Could Happen to You achieves a balance of intrigue and humor, bolstered by strong writing and captivating lead performances. Nicolas Cage stars as Charlie Lang, a cop low on funds who promises waitress Yvonne (Bridget Fonda) half of his lottery winnings if he wins. When fortune smiles upon him, their lives change drastically, thrusting them into the public eye due to their newfound wealth and lavish spending.The film effectively avoids flat characterizations, enhancing its rewatch value with rich narratives and captivating chemistry between Cage and Fonda.

7 Love Jones (1997)

Directed by Theodore Witcher

Unique and profound, Love Jones tells the story of two artists, Darius (Larenz Tate) and Nina (Nia Long), who explore their creative and romantic compatibility. Throughout the film, their relationship is marked by uncertainty and emotional conflict, enhancing its narrative depth.With exquisite cinematography and a rich R&B soundtrack, the film is a mature exploration of love. The understated performances of Tate and Long make it a timeless gem that resonates with audiences even decades later, thanks to its thoughtfully developed characters and a divergence from clichéd storytelling.

6 10 Things I Hate About You (1999)

Directed by Gil Junger

Heath Ledger as Patrick and Julia Stiles as Kat sitting on swings.

Adapted from Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You skillfully modernizes the classic tale within a high school setting. Featuring strong performances from Julia Stiles and Heath Ledger, the film artfully intertwines principles of feminism through Kat’s (Stiles) unapologetic character, giving it lasting relevance.Kat’s challenges and her strong beliefs resonate with audiences and reflect modern themes currently explored in rom-coms. The film’s witty dialogue, combined with delightful comedic timing from its ensemble cast, ensures its continued success across generations.

5 You’ve Got Mail (1998)

Directed by Nora Ephron

Tom Hanks and Meg Ryan looking confused at a counter in You've Got Mail

Starring the beloved duo Tom Hanks and Meg Ryan, You’ve Got Mail symbolizes the dawn of online romance amid 1990s culture. Their characters develop a connection through anonymous communication, only to discover they are rival business owners. Intriguingly, rather than suffering from its dated premise, the film’s nostalgic elements and online interactions feel refreshingly unique in contemporary viewings. This nostalgic charm not only highlights the undeniable chemistry between Hanks and Ryan but also showcases a timeless love story that resonates with viewers today.

4 The Truth About Cats & Dogs (1996)

Directed by Michael Lehmann

With echoes of Cyrano de Bergerac, this film presents a twist on the classic storyline. It follows Abby Barnes (Janeane Garofalo), a radio host and veterinarian, who, due to insecurities about her looks, enlists her stunning friend Noelle (Uma Thurman) to impersonate her on a date. The film is both heartfelt and humorous, with Garofalo delivering a standout performance. Despite some critique over perceptions of beauty, The Truth About Cats & Dogs dives deeper into the complexities of friendship and relationships. Its journey through self-acceptance makes it a memorable entry in the rom-com genre.

3 The Best Man (1999)

Directed by Malcolm D. Lee

Original cast of The Best Man posing together

In 1999, Taye Diggs starred in a variety of films, including the rom-com The Best Man. Diggs plays Harper Stewart, an author who soon discovers that his debut novel is inspired by the lives of his friends, leading to chaos on the day of his friend’s wedding.The film is filled with humor and poignant moments, encapsulated by an ensemble cast including Nia Long, Morris Chestnut, and Regina Hall, who brings fresh talent to the screen. The messy entanglements of friendship are relatable, making this film an enduring favorite among viewers seeking both laughter and heartfelt moments.

2 The Wedding Banquet (1993)

Directed by Ang Lee

Original cast of The Wedding Banquet (1993)

Part of Ang Lee’s “Father Knows Best”trilogy, The Wedding Banquet stands out for its poignant exploration of LGBTQ+ themes. The narrative follows Gao Wai-Tung (Winston Chao), a bisexual man navigating the complexities of family expectations and cultural identity as he plans a fake wedding to appease his traditional Taiwanese parents.Through relatable characters and heartfelt storytelling, the film remains impactful today, highlighting the balance of love, honesty, and cultural differences.

1 Notting Hill (1999)

Directed by Roger Michell

Julia Roberts and Hugh Grant laugh as they walk through London in Notting Hill

Written by renowned screenwriter Richard Curtis, Notting Hill features Julia Roberts and Hugh Grant in a delightful romantic narrative. Their characters, coming from starkly different worlds, attempt to forge a relationship, providing countless memorable moments throughout the film.Roberts and Grant’s chemistry is electric, making the film’s premise of an ordinary man falling for a celebrity timeless and continually engaging. The charm of this delightful rom-com allows it to be revisited repeatedly, serving as a quintessential example of the genre’s success during the ’90s.

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