10 Most Rewatchable '90s Rom-Com movies Ranked

The 1990s marked a golden era for romantic comedies, delivering a treasure trove of films that continue to enchant audiences with their timeless charm and captivating storylines. From heartwarming tales of love and laughter to quirky comedies that redefine the genre, these movies have left an indelible mark on popular culture. In this article, we’ll take a nostalgic journey through the 10 most rewatchable ’90s rom-coms, celebrating the iconic characters, memorable moments, and enduring appeal of these beloved classics. So, grab your popcorn and get ready to relive the magic of the ’90s era, where romance was in the air, and laughter was guaranteed.

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In the realm of ’90s rom-coms, Never Been Kissed stands out as a charming tale of love and redemption. Directed by Raja Gosnell, the film stars Drew Barrymore as Josie Geller, a junior reporter on a mission to write an article on teenage culture. However, things take an unexpected turn when Josie falls for her English teacher, Sam Coulson, played by Michael Vartan, while undercover at a high school.

10. Never Been Kissed (1999)

The allure of Never Been Kissed lies in its relatable storyline and endearing characters. Josie’s journey from an awkward journalist to a young woman finding love resonates with audiences, making it a delightful rewatch. Despite its far-fetched premise, the film’s sweetness and Barrymore’s heartfelt performance elevate it to a beloved ’90s classic.

Release Date: April 9, 1999
Runtime: 107 Minutes
Watch on: Starz

9. She’s All That (1999)

Directed by Robert Iscove, She’s All That may not be the pinnacle of high school romance, but it retains its status as a quintessential ’90s rom-com. Freddie Prinze Jr. stars as Zack Siler, a popular student who accepts a bet to transform Laney Boggs, played by Rachael Leigh Cook, into a prom queen after being dumped by his girlfriend.

She’s All That offers a familiar yet endearing take on the classic “ugly duckling” trope, complete with memorable characters and a stellar ensemble cast. Despite its predictable plot, the film’s charm lies in its nostalgic appeal, making it a go-to choice for fans of ’90s teen movies.

Release Date: January 29, 1999
Cast: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker, Jodi Lyn O’Keefe, Anna Paquin, Kieran Culkin
Runtime: 95 Minutes
Watch on: Paramount+

8. There’s Something About Mary (1998)

There’s Something About Mary, directed by Bobby and Peter Farrelly, epitomizes the outrageous yet irresistible humor of ’90s rom-coms. The film follows Ted, played by Ben Stiller, as he embarks on a quest to reconnect with his high school crush, Mary, portrayed by Cameron Diaz, years after a disastrous prom night.

With its blend of slapstick comedy and heartfelt romance, There’s Something About Mary offers a unique cinematic experience. Despite its crude humor, the film’s underlying message of love and redemption resonates with audiences, making it a beloved classic of the ’90s era.

Release Date: July 15, 1998
Runtime: 119 Minutes
Watch on: Hulu

7. The Wedding Singer (1998)

Directed by Frank Coraci, The Wedding Singer showcases the comedic talents of Adam Sandler and Drew Barrymore in a heartwarming tale of love and second chances. Sandler portrays Robbie Hart, a wedding singer whose life takes an unexpected turn when he meets Julia, played by Barrymore, a charming waitress engaged to the wrong man.

Filled with memorable moments and ’80s nostalgia, The Wedding Singer offers a delightful blend of romance and humor. Sandler and Barrymore’s on-screen chemistry shines through, making it a timeless favorite among fans of ’90s rom-coms.

Release Date: February 13, 1998
Cast: Adam Sandler, Drew Barrymore, Christine Taylor, Allen Covert, Matthew Glave, Ellen Albertini Dow
Runtime: 95 Minutes
Rent on: Apple

6. You’ve Got Mail (1998)

Directed by Nora Ephron, You’ve Got Mail is a quintessential ’90s rom-com that captures the magic of online romance in the early days of the internet. Starring Tom Hanks and Meg Ryan, the film follows bookstore owner Kathleen Kelly, played by Ryan, as she engages in an anonymous email exchange with her business rival, Joe Fox, portrayed by Hanks.

You’ve Got Mail charms audiences with its witty dialogue and endearing performances. Hanks and Ryan’s undeniable chemistry elevates the film, making it a timeless classic that celebrates the joys of love and connection in the digital age.

Release Date: May 28, 1999
Runtime: 124 Minutes
Watch on: Amazon

5. Clueless (1995)

Directed by Amy Heckerling, Clueless is a cult classic that redefines the high school rom-com genre with its sharp wit and iconic fashion. Alicia Silverstone stars as Cher Horowitz, a fashionable and popular teenager navigating the ups and downs of adolescence in Beverly Hills.

Clueless delights audiences with its witty dialogue and satirical take on teenage life in the ’90s. As an adaptation of Jane Austen’s Emma, the film offers a fresh and modern interpretation of the classic novel, making it a beloved favorite among fans of ’90s cinema.

Release Date: July 19, 1995
Runtime: 97 Minutes
Watch on: Paramount+

4. 10 Things I Hate About You (1999)

Directed by Gil Junger, 10 Things I Hate About You is a modern retelling of Shakespeare’s The Taming of the Shrew set in a high school setting. Starring Heath Ledger and Julia Stiles, the film follows the unlikely romance between bad boy Patrick Verona and independent-minded Kat Stratford, who initially clash but soon find themselves drawn to each other.

10 Things I Hate About You captivates audiences with its witty dialogue and heartfelt performances. Ledger and Stiles’ on-screen chemistry is electric, making it a standout film in the ’90s rom-com canon.

Release Date: March 31, 1999
Runtime: 97 Minutes
Watch on: Disney+

3. Notting Hill (1999)

Directed by Roger Michell, Notting Hill is a timeless romance that celebrates love in all its complexities. Starring Hugh Grant and Julia Roberts, the film follows the unlikely romance between bookstore owner William Thacker and Hollywood actress Anna Scott as they navigate the challenges of fame, fortune, and societal expectations.

Notting Hill enchants audiences with its charming storyline and captivating performances. Grant and Roberts’ on-screen chemistry is palpable, making it a beloved favorite among fans of ’90s rom-coms.

Release Date: May 28, 1999
Runtime: 124 Minutes
Watch on: Amazon

2. Sleepless in Seattle (1993)

Directed by Nora Ephron, Sleepless in Seattle is a classic romantic comedy that tugs at the heartstrings with its tale of love against the odds. Starring Tom Hanks and Meg Ryan, the film follows widower Sam Baldwin and journalist Annie Reed as they embark on a journey of love and destiny.

Sleepless in Seattle captivates audiences with its heartfelt storyline and irresistible charm. Hanks and Ryan’s on-screen chemistry is magical, making it a timeless classic that continues to resonate with audiences of all ages.

Release Date: June 25, 1993
Runtime: 105 Minutes
Watch on: Max

1. Pretty Woman (1990)

Directed by Garry Marshall, Pretty Woman is the epitome of ’90s romance, blending fairy tale charm with modern-day sensibilities. Starring Julia Roberts and Richard Gere, the film follows the unlikely romance between prostitute Vivian Ward and wealthy businessman Edward Lewis as they navigate the complexities of love and social class.

Pretty Woman enchants audiences with its iconic moments and unforgettable performances. Roberts shines as the vivacious Vivian, while Gere delivers a charismatic portrayal of Edward, making it a timeless classic that defines the essence of ’90s rom-coms.

Release Date: March 23, 1990
Runtime: 119 Minutes
Watch on: Hulu

In conclusion, the ’90s era was undoubtedly the golden age of romantic comedies, delivering a plethora of timeless classics that continue to captivate audiences to this day. From heartwarming tales of love and redemption to witty comedies that redefine the genre, these films have left an indelible mark on popular culture.

The rewatchability of ’90s rom-coms lies not only in their charming storylines and memorable characters but also in their ability to transport viewers to a simpler time. Despite the occasional cheesiness and unrealistic plotlines, these films offer a much-needed escape from reality, allowing audiences to indulge in the magic of romance and laughter.

Whether it’s the iconic pairing of Julia Roberts and Richard Gere in Pretty Woman, the irresistible chemistry between Tom Hanks and Meg Ryan in Sleepless in Seattle and You’ve Got Mail, or the comedic genius of films like There’s Something About Mary and The Wedding Singer, ’90s rom-coms continue to hold a special place in the hearts of movie lovers everywhere.

As we look back on these beloved classics, it’s clear that the ’90s era has left a lasting legacy in the world of romantic comedies, inspiring future generations of filmmakers and reminding us of the timeless appeal of love, laughter, and happily ever afters. So, the next time you’re in need of a feel-good movie night, why not revisit one of these rewatchable ’90s rom-coms and experience the magic all over again?