10 Best Movies From The Golden Age Of Rom-Coms, Ranked

Once upon a time, the romantic comedy was one of the biggest box office draws, and every year countless rom-coms were released to the delight of enthusiastic audiences. The Golden Age of Rom-Coms was generally accepted to have occurred from the late 1980s to the early 2000s and throughout this period there were many classic releases in both the United States and Britain. While the heyday of the rom-com may have long since passed, the very best movies released during this time are still beloved and widely watched by those looking for a hilarious, light-hearted love story.

The Golden Age of Rom-Coms made stars out of its cast members as the stuttering, endearing charm of Hugh Grant made him a mainstay of the British rom-com, and the alluring girl-next-door beauty of Julia Roberts turned her into a Hollywood icon. With clever and witty scripts from acclaimed screenwriters like Richard Curtis and Nora Ephron, during this period the rom-com reached its peak and since then there have been very few releases that could compete with the best from this era. The Golden Age of Rom-Coms was a great time for moviemaking with some truly exceptional movies.

10 Notting Hill (1999)

Directed by Roger Michell

During the Golden Age of Rom-Coms, Hugh Grant stood as the quintessential handsome British leading man and Julia Roberts was the definitive angelic American, that’s why it was such a treat to see the two of them together in Notting Hill. Grant played a humble bookshop owner and Roberts was a famous actress who happened to walk into his Notting Hill store, the then two entered a whirlwind romance that was challenged by distance and the pitfalls of Roberts’ fame. A funny, heartfelt, and beloved rom-com, Notting Hill was written by Richard Curtis and was a classic of the era.

9 Clueless (1995)

Directed by Amy Heckerling

From the fashion to the music, everything about Clueless just screamed 1995 and it was all the better for it. With a plot that focused on the beautiful, popular, and rich high school student Cher Horowitz (Alicia Silverstone) and a new classmate, Tai Frasier (Brittany Murphy), in need of a makeover, Clueless was more than just a box office success as it had a noticeable impact on fashion trends at the time (via NPR) and acted as a cultural touchstone for that moment in pop culture. A loose adaptation of Jane Austen’s Emma, Clueless was stylistically 1990s, but thematically eternal.

8 Pretty Woman (1990)

Directed by Garry Marshall

When Pretty Woman was released in 1990 it exceeded all expectations and became the fourth highest-grossing movie of all time taking in $463,406,268 at the worldwide box office (via Box Office Mojo.) The pairing of Julia Roberts as Vivian Ward, a Hollywood escort, and Richard Gere, as wealthy businessman Edward Lewis, entering a week-long relationship deeply connected with viewers as its yuppie fantasy showcased the power of love can trump the allure of money. An unusually risque exploration of modern romance, the astounding success of Pretty Woman showcased just how much audiences were responding to rom-coms during this Golden Age.

7 High Fidelity (2000)

Directed by Stephen Frears

In an unusual juxtaposition of the rom-com genre, High Fidelity focused on the consequences of a break-up for a young record store owner whose life revolved around sharing his encyclopedic knowledge of music with his slacker co-workers. A stylish movie with a fantastic soundtrack, High Fidelity was led by John Cusack as Rob Gordan but featured a standout performance by Jack Black as employee-turned-musician Barry Judd. A funny, insightful, and witty exploration of stunted adolescence, High Fidelity was about a man who needed to make peace with his obsessive need to catalog and rank his existence and just learn to love.

6 My Big Fat Greek Wedding (2002)

Directed by Joel Zwick

As the highest-grossing rom-com of all time in America (via Box Office Mojo), My Big Fat Greek Wedding was a runaway success whose hilarious exploration of immigrant family dynamics, sharp script, and compelling performance by Nia Vardalos connected with audiences. My Big Fat Greek Wedding explored the complexity of a non-Greek man (John Corbett) who struggled to gain expectance from his girlfriend’s family after they fell in love. A laugh-out-loud portrayal of difficulties faced by second-generation immigrants, sadly, the success of My Big Fat Greek Wedding only worked once, and its two sequels left a lot to be desired.

5 Four Weddings And A Funeral (1994)

Directed by Mike Newell

A true classic of the Golden Age of Rom-Coms, Four Weddings and a Funeral was the movie that solidified Hugh Grant’s status as an awkwardly endearing and charming leading man whose romance with Carrie (Andie MacDowell) developed throughout several chance encounters at his friends’ social occasions. With a light-hearted but effective script by Richard Curtis and a heartfelt story that avoided sappy sentimentality, Four Weddings and a Funeral has consistently ranked among the best rom-coms ever made. An unexpected success, Four Weddings and a Funeral was the highest-grossing British movie (via Box Office Mojo) at the time of its release.

4 Love Actually (2003)

Directed by Richard Curtis

While Love Actually has most commonly been discussed as a festive favourite this endearing holiday ensemble comedy also stood as a compelling rom-com even outside of the Christmas period. With an astounding cast of the best comedic actors in Britain, the ten separate stories of Love Actually came together to create an interconnected romance that tugged at the heartstrings while keeping the laughs consistent. A cult favorite, Love Actually was more than the sum of its parts and has become annual viewings for countless rom-com lovers.

3 Bridget Jones’s Diary (2001)

Directed by Sharon Maguire

Renée Zellweger delivered what just might be her best performance as the down-on-her-luck 32-year-old writer searching for meaning and happiness in her life, Bridget Jones. In the years since its release, Bridget Jones’s Diary became entrenched in pop culture, and as a loose adaptation of Pride and Prejudice its love triangle plot and charming story made it an enduring and beloved classic of the Golden Age of Rom-Coms. While the Bridget Jones’s Diary sequels can’t stand up against the original, Zellweger has consistently shone as the hapless and hopeful Bridget Jones.

2 10 Things I Hate About You (1999)

Directed by Gil Junger

10 Things I Hate About You acted as the breakout roles for Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt in a modernization of William Shakespeare’s The Taming of the Shrew. It was a clever and funny story about high school dating drama, the desperation of adolescent romance, and the extraordinary allure of two unlikely love interests coming together. 10 Things I Hate About You stood as one of the best teen movies ever made was boosted by an incredible performance by Ledger as Patrick Verona, the Australian bad boy hired to date at anti-social sister Kat (Stiles.)

1 When Harry Met Sally… (1989)

Directed Rob Reiner

The greatest of all releases during the Golden Age of Rom-Coms was When Harry Met Sally… which acted as a touching journey about how friendship can turn into love over the years and the complexity of ensuring this does not destroy the connection. With unmatched chemistry, Billy Crystal and Meg Ryan turned the story of Harry Burns and Sally Albright into a stone-cold classic of the rom-com genre that still held up 35 years after its release. When Harry Met Sally… featured a sharp screenplay by Nora Ephron was ranked number six in AFI’s top romantic comedies of all time.

Sources: NPR, Box Office Mojo (Pretty Woman), Box Office Mojo (My Big Fat Greek Wedding), Radio Times, Box Office Mojo (Four Weddings and a Funeral), AFI