While1990s 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-comswith 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 evolvedout 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.Filmslike Ang Lee’sThe Wedding Banquetand Theodore Witcher’sLove Jonestell 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 fewtragically dated elements of ’90s rom-coms,many movies in the sub-genre get better with every rewatch.
Only You
Cast
Only You (1994) follows the journey of Faith Corvatch, played by Marisa Tomei, who believes she is destined to find her soulmate named Damon Bradley. With Robert Downey Jr. co-starring, the romantic comedy takes Faith from Pennsylvania to Italy in a whimsical quest for true love, blending elements of fate and serendipity under Norman Jewison’s direction.
Following its mid-’90s release,Only Youreceived mixed critical reviews and the fantasy elements in the film certainly aren’t for everyone. Still, the film featuresRobert Downey Jr. in a rare romantic roleandMarisa 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.”
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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 praisedand are the best part of the film.
Never Been Kissed
Never Been Kissed follows Josie Geller, played by Drew Barrymore, a copy editor who goes undercover as a high school student for an investigative report. Directed by Raja Gosnell, the film explores themes of adolescence and personal growth as Josie navigates her second chance at high school life. Supporting cast includes David Arquette, Michael Vartan, and Molly Shannon.
LikeOnly You, the implausible story inNever Been Kissedhas 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 followsBarrymore’s Josie Geller, a reporter in her 20swhose high school years weren’t defined by adolescent romance. When Josie gets an assignment 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 ofNever Been Kissed,the film has earned a passionate fan basemade up of people who find parts of themselves in Josie’s experience. Barrymore has also since reprised the role on her self-titled talk show.
It Could Happen to You
It Could Happen to You is a romantic comedy film directed by Andrew Bergman. Nicolas Cage stars as a New York City police officer who, unable to tip a waitress played by Bridget Fonda, promises her half of any future lottery winnings. When he wins, complications ensue as he struggles with newfound wealth and relationships. The film explores themes of generosity, integrity, and the impact of unexpected fortune.
Inspired by a real-life story,It Could Happen to Youis by no means a perfect romantic comedy, butit 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 aboutIt 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.
Love Jones
Love Jones is a romantic drama set in Chicago, focusing on the budding relationship between Darius Lovehall, a poet, and Nina Moseley, a photographer. As they explore their connection, the film delves into themes of love and friendship amidst a backdrop of artistic expression and personal challenges.
Both moody and mature,Love Jonesis a rare romantic dramedy that doesn’t come around often. The film followsthe 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.
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 makesLove Jonesso unique and rewarding with every rewatch.
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 makesLove Jonesso unique and rewarding with every rewatch. The absence of cliché writing also helps the film age well decades later.
10 Things I Hate About You
Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is a modern retelling of the classic play, set against the backdrop of a 90s Seattle high school. When social outcast Patrick Verona is paid to try and win over antisocial Kat Stratford in order so her younger sister will be allowed to date, he and Kat find an unexpected connection forming between them. Julia Stiles and Heath Ledger star as Kat and Patrick, with a further cast that includes Joseph Gordon-Levitt, Larisa Oleynik, David Krumholtz, Andrew Keegan, and Larry Miller.
It’s not entirely uncommon forteen movies to draw inspiration from William Shakespeare’s work, but one of the movies that does it best is10 Things I Hate About You. Tellinga modernized version of Shakespeare’sThe 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 allowed10 Things I Hate About Youto 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.
You’ve Got Mail
Directed by Nora Ephron, You’ve Got Mail follows Joe and Kathleen, two strangers who meet in an AOL chatroom and begin a relationship over email, unaware that they are actually a lot more connected to one another than they think. Tom Hanks and Meg Ryan star as Joe and Kathleen, with a further cast that includes Parker Posey, Jean Stapleton, Dave Chappelle, and Greg Kinnear.
Tom Hanks and Meg Ryan led a handful of rom-comstogether during the ’90s, but their best is widely considered to beYou’ve Got Mail. The film depictsthe growing online romance between Hanks and Ryan’s charactersthat becomes complicated once it’s revealed the anonymous users are business rivals. Despitethe film being fixed in ’90s culture, emphasizing the use of online chatrooms, the dated elements ofYou’ve Got Mailsurprisingly 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 likeYou’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.
The Truth About Cats & Dogs
The Truth About Cats & Dogs is a romantic comedy featuring a veterinarian and radio host with self-esteem issues, played by Janeane Garofalo. She enlists her model friend, portrayed by Uma Thurman, to impersonate her when a charming man, played by Ben Chaplin, expresses interest in meeting her.
Several movies are loosely inspired by Edmond Rostand’s play,Cyrano de Bergerac, includingThe Ugly Truth,The Half of It, andThe Truth About Cats & Dogs. The latter is a romantic comedy that swaps genders and follows veterinarian andradio host Abby Barnes (Janeane Garofalo) after she’s asked on a date by a calleron her show. Insecure about her appearance, Abby asks her model friend Noelle (Uma Thurman) to pose as her on the date.
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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 & Dogsremains a commendable rom-com that’s about a romantic relationship as much as it is about the friendship between Noelle and Abby.
The Best Man
The Best Man, directed by Malcolm D. Lee, follows writer Harper Stewart, who struggles to conceal that his bestselling novel is based on his friends' lives. Set to be the best man at a wedding, Harper faces tension as an advance copy of the book circulates among the group.
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 comedyThe 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 inThe 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.
The Wedding Banquet
The Wedding Banquet is a 1993 film directed by Ang Lee. The story follows Wai-Tung, a Taiwanese-American man who stages a marriage of convenience to satisfy his traditional parents, unaware that this decision will complicate his relationship with his partner Simon. Set against a backdrop of cultural expectations and familial obligations, the film navigates themes of identity, love, and acceptance.
As the second installment in Ang Lee’s “Father Knows Best” trilogy,The Wedding Banquetremains an underratedLGBTQ+ rom-com. The film sees Gao Wai-Tung (Winston Chao), a bisexual 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.
The Wedding Banquethas a 96% rating onRotten Tomatoes.
What makesThe Wedding Banquetwork, 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.
Notting Hill
Notting Hill is a romantic comedy featuring Hugh Grant as London bookstore owner William Thacker. The film follows Thacker’s unexpected romance with actress Anna Scott, played by Julia Roberts, as they navigate the challenges posed by their contrasting lifestyles.
Known for writing successful romantic comedy films likeBridget Jones’s Diary,Love Actually, andFour Weddings and a Funeral, Richard Curtis also wrote the screenplay forNotting Hill.The film stars Julia Robertsand Hugh Grant, both known for their romantic comedy roles around the time. The film tells the story of howRoberts' 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 ofNotting Hill, and what makes it easy to watch repeatedly years later, are the performances of Roberts and Grant.
The undeniable strength ofNotting Hill, and what makes it easy to watch repeatedly years later, are the performances of Roberts and Grant. Fromthe rom-com’s initial meet-cuteat 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.
