Who doesn’t love a good rom-com every now and then? The best ’90s rom coms are perfect for a date night movie or just a cozy night in. They are also some of the most captivating and heartwarming romance movies from the ’90s overall. Let’s embark on a journey through the best ’90s romantic comedies, ranked from the most enchanting to the slightly less mesmerizing based on user opinions.
This list unveils a collection of delightful ’90s romantic comedies that unravel stories of protagonists who, against all odds, stumble upon love in the most unexpected corners of the world. Some of these movies lean more towards drama, but still manage to sprinkle in comedic moments, while others embrace pure slapstick humor. Many of these films have gained a devoted following and have left an indelible mark on the tapestry of cinema history.
So, what treasures can you anticipate discovering on this list of the best ’90s romantic comedies? Prepare yourself for some of the most adored romantic comedies of all time starring the dynamic duo of Tom Hanks and Meg Ryan. Films like Joe Versus the Volcano, Sleepless in Seattle, and You’ve Got Mail brought boundless joy to audiences throughout the ’90s. Julia Roberts also graced the silver screen with her charm, starring in unforgettable ’90s romantic comedies such as Pretty Woman and My Best Friend’s Wedding.
One line that still echoes in our hearts from a ’90s romantic comedy is “You had me at hello,” spoken in the 1996 film Jerry Maguire. Other remarkable films on this list include The Wedding Singer, Groundhog Day, and As Good As It Gets.
Now, the time has come for you to play the role of the ultimate movie critic and decide which film deserves the highest accolade on this list. Share your favorites and let us know your thoughts!
(Note: The most polarizing movie on this list is American Pie.)
1. 10 Things I Hate About You
Welcome to 10 Things I Hate About You, a movie that puts a modern spin on Shakespeare while blending teenage romance with sharp comedy. The story takes place in an American high school and revolves around the Stratford sisters: the rebellious Kat, played by Julia Stiles, and her popular younger sister, Bianca, played by Larisa Oleynik.
The plot kicks off when a new student named Cameron, played by Joseph Gordon-Levitt, falls head over heels for Bianca. However, he quickly discovers that their father has a strict rule about dating. Determined to win Bianca’s heart, Cameron devises a plan involving the school’s bad boy, Patrick Verona, played by Heath Ledger, to win over Kat.
As the story unfolds, we are treated to clever banter, unexpected romances, and a deep exploration of teenage angst, love, and self-discovery. The film stands out for its memorable performances and sharp wit, making it a delightful journey into the world of young love and personal transformation.
Directed by: Gil Junger
Actors: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
2. Pretty Woman
In the classic rom-com Pretty Woman, we witness the unlikely love story between Edward Lewis (played by Richard Gere), a well-off businessman, and Vivian Ward (played by Julia Roberts), a feisty and street-smart woman. Their encounter sparks a rollercoaster ride as they try to navigate the challenges of their contrasting lives. Business and pleasure intertwine, leading to some heartfelt moments that truly tug at your heartstrings. Directed by Garry Marshall, this film is renowned for its clever banter and unforgettable acting, with Roberts even earning an Oscar nod for her captivating portrayal of Vivian.
Directed by: Garry Marshall
Actors: Richard Gere, Julia Roberts, Ralph Bellamy
3. Sleepless in Seattle
In Sleepless in Seattle, we meet Sam Baldwin (played by Tom Hanks), a widower who becomes the center of attention when his son Jonah (played by Ross Malinger) calls into a popular radio talk show. Little did Sam know that his heartfelt story would capture the interest of people all across the nation. Enter Annie Reed (played by Meg Ryan), a journalist who becomes captivated by Sam’s story and finds herself drawn to him.
As fate would have it, their paths eventually cross in a momentous encounter at the iconic Empire State Building. This romantic drama, skillfully directed by Nora Ephron, received high praise and even earned two Oscar nominations. It’s renowned for its delightful combination of humor and emotional depth, showing us that love knows no boundaries.
Sleepless in Seattle is a heartwarming tale that reminds us of the power of love to transcend all obstacles. Whether you’re a fan of romantic comedies or simply enjoy a touching story, this film is sure to leave a lasting impression.
Directed by: Nora Ephron
Actors: Tom Hanks, Meg Ryan, Bill Pullman
4. You’ve Got Mail
In the romantic comedy You’ve Got Mail, we meet Kathleen Kelly, a charming bookstore owner in the heart of New York City. She’s got this irresistible attraction towards an anonymous pen pal she met online, but little does she know that her mystery man is actually her arch-nemesis in the business world, Joe Fox. He’s the big shot behind a huge bookselling chain. While their love story blossoms in the digital realm against the backdrop of the bustling Big Apple, their real-life rivalry takes a surprising twist. Directed by Nora Ephron, this delightful film delves into the complexities of modern romance and identity in the age of the internet.
Directed by: Nora Ephron
Actors: Tom Hanks, Meg Ryan, Parker Posey
5. While You Were Sleeping
In the rom-com film While You Were Sleeping, Lucy Moderatz, played by Sandra Bullock, works as a token collector for the Chicago Transit Authority. She secretly admires a handsome commuter named Peter Callaghan, portrayed by Peter Gallagher. One day, Lucy saves Peter from an oncoming train after he falls onto the tracks. Unfortunately, Peter ends up unconscious in the hospital.
Here’s where things get interesting: Peter’s family mistakenly believes that Lucy is his fiancée. Jack Callaghan, Peter’s brother, portrayed by Bill Pullman, is initially skeptical of Lucy but also feels drawn towards her. As Peter starts to recover, Lucy finds herself caught up in a comical and unexpected romantic dilemma.
This delightful romantic comedy, released in 1995, captured the hearts of many viewers. Sandra Bullock’s performance in the lead role even earned her a Blockbuster Entertainment Award for Favorite Actress.
Directed by: Jon Turteltaub
Actors: Sandra Bullock, Bill Pullman, Peter Gallagher
Located in the heart of Beverly Hills, we meet Cher Horowitz, a high school student who proudly labels herself as a fashionista and a matchmaker. Alicia Silverstone brings this iconic character to life in the comedy-drama film, Clueless, directed by Amy Heckerling. Throughout the movie, we witness Cher navigate the challenges of adolescence, juggling love interests, and striving to maintain her social status. Assisting her in her various misadventures is her best friend Dionne Davenport, played by Stacey Dash.
This delightful modern adaptation of Jane Austen’s Emma brilliantly captures the angst of teenage life and the complexities of young love. Cleverly blending humor and drama, Clueless not only entertains but also subtly touches on important social issues, giving it a timeless quality.
Directed by: Amy Heckerling
Actors: Alicia Silverstone, Stacey Dash, Brittany Murphy
7. Notting Hill
Notting Hill is a charming romantic comedy that takes place in the picturesque district of London. It tells the story of William Thacker, a humble bookstore owner, who unexpectedly crosses paths with Anna Scott, a global superstar and American actress. Their meeting in his shop sets off a series of events that blend the ordinary with the glamorous. Fame, privacy, and love become the challenges they must navigate as their worlds collide. Directed by Roger Michell, this film is a delightful exploration of two contrasting lives merging in an unexpected place.
Directed by: Roger Michell
Actors: Julia Roberts, Hugh Grant, Hugh Bonneville
8. She’s All That
She’s All That, directed by Robert Iscove, is a 1999 romantic comedy that revolves around Zack Siler, a high school jock played by Freddie Prinze Jr. After getting dumped by his girlfriend, Zack makes a bet that he can turn any girl into prom queen in just six weeks. That’s when Laney Boggs, an introverted art student portrayed by Rachael Leigh Cook, enters the scene as the subject of Zack’s transformation experiment. As Zack embarks on this challenge, he starts to experience unexpected emotions. This feel-good movie delves into the themes of popularity, being true to oneself, and the unpredictability of love in the high school environment.
Directed by: Robert Iscove
Actors: Freddie Prinze, Rachael Leigh Cook, Matthew Lillard
9. Father of the Bride
The movie Father of the Bride is a heartwarming comedy that tells the story of George Banks, played by Steve Martin. George is a loving father who is suddenly thrown into the chaotic world of wedding planning when his daughter Annie, played by Kimberly Williams-Paisley, announces her engagement.
As the wedding preparations unfold, George finds himself dealing with escalating costs, quirky wedding planners, and the realization that his nest will soon be empty. Throughout all the comedic chaos, he relies on his patient wife Nina, played by Diane Keaton, to help him navigate this new territory.
Father of the Bride is a light-hearted film that explores the bonds of family and the challenges that come with changing times. It was a big hit at the box office in 1991 and even earned Steve Martin a Golden Globe nomination for Best Actor.
Directed by: Charles Shyer
Actors: Steve Martin, Diane Keaton, Kimberly Williams-Paisley
10. The Wedding Singer
The Wedding Singer, a romantic comedy released in 1998, follows the story of Robbie Hart, a charming and kind-hearted small-town wedding singer portrayed by Adam Sandler. Robbie is eagerly preparing to marry his long-term girlfriend, Linda, played by Angela Featherstone. However, the plot takes an unexpected twist when Linda leaves him standing alone at the altar.
Enter Julia Sullivan, a sweet and lovable waitress played by Drew Barrymore. Julia is engaged to a self-centered tycoon, adding more complexity to the story. As fate would have it, Robbie and Julia’s paths cross, and they begin to feel a magnetic pull towards each other.
The Wedding Singer offers a delightful and heartwarming tale of love, laughter, and a touch of 80s nostalgia. The film effortlessly combines humor and romance, leaving viewers smiling and feeling warm inside. It serves as a reminder that sometimes, love can find its way into our lives when we least expect it.
Directed by: Frank Coraci
Actors: Adam Sandler, Drew Barrymore, Christine Taylor
11. My Best Friend’s Wedding
In the romantic comedy “My Best Friend’s Wedding,” Julianne Potter, played by Julia Roberts, finds herself in a tricky romantic situation. Her longtime friend, Michael O’Neal (Dermot Mulroney), drops the bombshell of his engagement to the lively and youthful Kimmy Wallace (Cameron Diaz), leaving Julianne to confront her hidden feelings for him. With the wedding drawing near, Julianne embarks on a hilarious journey of self-discovery and unrequited love. Rupert Everett steals the show as George Downes, Julianne’s trusted confidant, adding an extra layer of complexity to this tale of love and friendship. Directed by P.J. Hogan, this film takes a unique and captivating look at relationships.
Directed by: P.J. Hogan
Actors: Julia Roberts, Dermot Mulroney, Cameron Diaz