While 1990s romantic comedies feature certain clothing items, references, and phrases that aren’t in style at the moment, that doesn’t stop them from being highly rewatchable. The ’90s was a great decade for rom-coms with a solid film guaranteed to be released each year. The grand romantic gestures and use of the decade’s biggest stars are just two aspects of ’90s rom-coms that make a rewatch all the more fun. The romantic comedy sub-genre has evolved out of necessity in recent years, centering around more diverse characters and love stories.

Yet, that’s not to say the ’90s didn’t try to do this earlier as well. Films like Ang Lee’s The Wedding Banquet and Theodore Witcher’s Love Jones tell refreshing love stories that don’t often come to mind when thinking of traditional ’90s rom-coms — their originality therefore increasing their rewatch value years later. Still, even the more stereotypical, cheesy acts of romance seen in ’90s films are easy to get swept up in, making audiences more likely to rewatch them time and time again. Despite a few tragically dated elements of ’90s rom-coms, many movies in the sub-genre get better with every rewatch.

10

Only You (1994)

Directed by Norman Jewison

Following its mid-’90s release, Only You received mixed critical reviews and the fantasy elements in the film certainly aren’t for everyone. Still, the film features Robert Downey Jr. in a rare romantic role and Marisa Tomei delivers an underrated performance, making it a film that’s fun to frequently revisit. The film follows Tomei’s Faith, who, since she was a young girl, believes she’s destined to marry a man named “Damon Bradley.”

As an adult, Faith learns that “Damon Bradley” is traveling to Italy, and she sets out to meet him. Of course, things don’t work out entirely how Faith planned, but she gets a happy ending after all. While the film did earn a mixed critical response and hasn’t been redeemed as a cult classic today, Tomei and Downey’s performances have been praised and are the best part of the film.

9

Never Been Kissed (1999)

Directed by Raja Gosnell

Like Only You, the implausible story in Never Been Kissed has made it difficult for critics to enjoy the film over the years. Yet, it’s Drew Barrymore’s leading performance that saves the movie, allowing it to grow a cult following. The film follows Barrymore’s Josie Geller, a reporter in her 20s whose high school years weren’t defined by adolescent romance. When Josie gets an ᴀssignment and must go undercover at a high school, she gets the chance to reinvent her teenage persona.

Barrymore is supported by actors such as David Arquette and Molly Shannon, but she grounds much of the film and its lovable absurdities with her charming performance. In the years since the release of Never Been Kissed, the film has earned a pᴀssionate fan base made up of people who find parts of themselves in Josie’s experience. Barrymore has also since reprised the role on her self-тιтled talk show.

8

It Could Happen To You (1994)

Directed by Andrew Bergman

Inspired by a real-life story, It Could Happen to You is by no means a perfect romantic comedy, but it has a solid rewatch value thanks to its writing and lead performances. The film sees Nicolas Cage as officer Charlie Lang, who is short on cash and offers a waitress, Bridget Fonda’s Yvonne, a sum of his lottery earnings should he win. Upon discovering he did win the lottery, Charlie and Yvonne are thrust into the spotlight due to their generous spending habits.

Despite Yvonne and Charlie’s sudden wealth and budding connection causing problems in their respective relationships, there’s still a lot to love about It Could Happen to You. Jane Anderson’s screenplay avoids flat characterization, even for supporting characters like Charlie’s wife, Muriel. Cage and Fonda also have great chemistry that draws audiences in and has them invested in their connection and unique predicament.

7

Love Jones (1997)

Directed by Theodore Witcher

Both moody and mature, Love Jones is a rare romantic dramedy that doesn’t come around often. The film follows the love story of two artists in their twenties, Darius (Larenz Tate) and Nina (Nia Long), who bond over their shared interests. The majority of the movie sees the two unsure of whether they want a deeper connection with one another, leading to a mix of jealousy and confusion surrounding the nature of the relationship.

Ernest Holzman’s cinematography is as stylish and rich as the film’s R&B-heavy soundtrack, and it supports the understated performances of Tate and Long. The actors may not be as comedic or bold in their performances as other rom-com stars, but the subtlety of the film is what makes Love Jones so unique and rewarding with every rewatch. The absence of cliché writing also helps the film age well decades later.

6

10 Things I Hate About You (1999)

Directed by Gil Junger

It’s not entirely uncommon for teen movies to draw inspiration from William Shakespeare’s work, but one of the movies that does it best is 10 Things I Hate About You. Telling a modernized version of Shakespeare’s The Taming of the Shrew, the film is set in high school and centers around the contrived relationship between Kat Stratford (Julia Stiles) and Patrick Verona (Heath Ledger). The film features likable characters, and it effectively transforms Shakespeare’s comedy with its feminist tones.

Such feminist ideals are presented through Kat, who is unapologetically herself throughout the film. It’s partially the characterization of Kat that has allowed 10 Things I Hate About You to get better with age. Not only do her beliefs continue to be relevant in the real world, but they’re often introduced in modern rom-coms as well. The cast’s performances are also delightful, as audiences are treated with the well-timed comedic talent of David Krumholtz and the effortless charm of Ledger.

5

You’ve Got Mail (1998)

Directed by Nora Ephron

Tom Hanks and Meg Ryan led a handful of rom-coms together during the ’90s, but their best is widely considered to be You’ve Got Mail. The film depicts the growing online romance between Hanks and Ryan’s characters that becomes complicated once it’s revealed the anonymous users are business rivals. Despite the film being fixed in ’90s culture, emphasizing the use of online chatrooms, the dated elements of You’ve Got Mail surprisingly work well in its favor.

The dated premise doesn’t diminish the excitement of modern viewings, as it, oddly enough, still feels unique. The nostalgic aspects are appreciated by audiences, both those who grew up with online chatrooms and those whose understanding of them comes from movies like You’ve Got Mail. In a way, the nostalgia of the late ’90s rom-com also draws attention to Hanks and Ryan’s power as an acting duo at the time, with the two being immensely lovable on screen.

4

The Truth About Cats & Dogs (1996)

Directed by Michael Lehmann

Several movies are loosely inspired by Edmond Rostand’s play, Cyrano de Bergerac, including The Ugly Truth, The Half of It, and The Truth About Cats & Dogs. The latter is a romantic comedy that swaps genders and follows veterinarian and radio host Abby Barnes (Janeane Garofalo) after she’s asked on a date by a caller on her show. Insecure about her appearance, Abby asks her model friend Noelle (Uma Thurman) to pose as her on the date.

The film is witty and sweet and features a standout performance from Garofalo, who’d starred in another romantic comedy, Reality Bites, a few years before. There have been a few criticisms of the film about whether Garofalo’s character could be considered unattractive. Yet, The Truth About Cats & Dogs remains a commendable rom-com that’s about a romantic relationship as much as it is about the friendship between Noelle and Abby.

3

The Best Man (1999)

Directed by Malcolm D. Lee

1999 was a busy year for Taye Diggs, where the actor starred in a comedy, coming-of-age, and horror movie. Diggs also led the romantic comedy The Best Man, where he plays author Harper Stewart. On his way to his friend’s wedding where he’ll be serving as best man, Harper learns that his debut novel has been selected by Oprah’s Book Club. What starts as great news for the up-and-coming author, quickly turns into chaos when his friends are surprised to learn the book is inspired by their real-life stories.

Audiences quickly, and willingly, get wrapped up in The Best Man‘s friend group drama, which is comedically captured by the film’s talented ensemble, made up of actors like Nia Long, Morris Chestnut, and Regina Hall, the latter making her film debut. The complications that stem from Harper’s personal book are delightfully messy and truly never get old.

2

The Wedding Banquet (1993)

Directed by Ang Lee

As the second installment in Ang Lee’s “Father Knows Best” trilogy, The Wedding Banquet remains an underrated LGBTQ+ rom-com. The film sees Gao Wai-Tung (Winston Chao), a biSєxual man, living with his partner in New York City. Wai-Tung has yet to come out to his traditional Taiwanese parents, who’ve been insisting on finding him a wife. Wai-Tung’s situation quickly becomes chaotic when his parents visit him for the fake wedding he orchestrated with a female tenant to please them.

What makes The Wedding Banquet work, and why it fails to get old with age, is the realistic characters in the film. One of the more realistic and earnest romantic comedies of the decade, Lee’s film understands the purpose of its characters’ stories is not purely to entertain audiences. The cultural differences and Wai-Tung’s struggle to be honest with his parents are real, and his story is told with a lot of heart.

1

Notting Hill (1999)

Directed by Roger Michell

Known for writing successful romantic comedy films like Bridget Jones’s Diary, Love Actually, and Four Weddings and a Funeral, Richard Curtis also wrote the screenplay for Notting Hill. The film stars Julia Roberts and Hugh Grant, both known for their romantic comedy roles around the time. The film tells the story of how Roberts’ celebrity character meets the owner of a book store played by Grant. Despite their vastly different lifestyles, the pair attempt to make a relationship work.

The undeniable strength of Notting Hill, and what makes it easy to watch repeatedly years later, are the performances of Roberts and Grant. From the rom-com’s initial meet-cute at the start of the film, to the very end, the actors are completely in sync. Additionally, the far-fetched possibility of falling in love with a celebrity is timeless and always fun to watch play out.