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Summary

  • The Golden Age of Rom-Coms showcased stars like Hugh Grant & Julia Roberts, with witty scripts and exceptional movies.
  • Notting Hill, Clueless, & Pretty Woman are beloved rom-coms from this era, with unique storylines and memorable characters.
  • Other classics like High Fidelity, My Big Fat Greek Wedding, & more made this period truly great for moviemaking.

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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

Notting Hill

Starring Julia Roberts and Hugh Grant, Notting Hill is a romantic comedy that tells the story of a charming British bookseller who falls in love with an American movie star. Released in 1999, the romantic comedy written by Bridget Jones’s Diary and Love Actually screenwriter Richard Curtis was a critical and box office success.

Director
Roger Michell

Release Date
May 13, 1999

Runtime
124minutes

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

Cher on the phone in Clueless

Clueless

A modern reimagining of Jane Austen’s 1815 novel Emma, the iconic teen comedy Clueless stars Alicia Silverstone as Cher Horowitz, a rich and popular high schooler who takes a transfer student under her wing. Between making over her friends and trying to play matchmaker for her teachers, Cher finds herself increasingly unlucky in love – only to find it much closer to home than she would have thought. Brittany Murphy, Paul Rudd, and Donald Faison also star.

Director
Amy Heckerling

Release Date
July 19, 1995

Cast
Alicia Silverstone , Stacey Dash , Brittany Murphy , Paul Rudd , Donald Faison , Elisa Donovan

Runtime
97 minutes

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.

A loose adaptation of Jane Austen’s Emma, Clueless was stylistically 1990s, but thematically eternal.

8 Pretty Woman (1990)

Directed by Garry Marshall

A closeup of Richard Gere and Julia Roberts in the promotional poster for Pretty Woman

Pretty Woman

Directed by Gary Marshall, Pretty Woman stars Julia Roberts and Richard Gere as Vivian Ward and Edward Lewis. Lewis is a wealthy New York businessman who hires Hollywood sex worker Ward to accompany him during his stay in Los Angeles. Initially wary of each other, the couple’s relationship grows steadily deeper over Lewis’ stay, causing Ward to begin to rethink her career path.  

Release Date
March 23, 1990

Runtime
119 minutes

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

High Fidelity

Adapted from a British novel of the same name, High Fidelity stars John Cusack as Rob Gordon, a record store employee who, after a bad breakup with his latest girlfriend Laura, sets out to find a reason for all of his failed relationships and tries to win Laura back in the process. The cast includes Iben Hjejle, Jack Black, and Lisa Bonet. 

Director
Stephen Frears

Release Date
March 31, 2000

Cast
Jack Black , Lisa Bonet , Lili Taylor , Catherine Zeta-Jones , John Cusack

Runtime
113 minutes

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

Toula and Ian in their wedding attire, driving away after the event in My Big Fat Greek Wedding.

My Big Fat Greek Wedding

Director
Joel Zwick

Release Date
February 22, 2002

Cast
Nia Vardalos , Michael Constantine , Christina Eleusiniotis , Kaylee Vieira , John Kalangis , Lainie Kazan

Runtime
95 minutes

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.

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

Carrie (Andie MacDowell) smiling hugged by Charles (Hugh Grant) in Four Weddings and a Funeral

Four Weddings and a Funeral

Director
Mike Newell

Release Date
March 9, 1994

Cast
Hugh Grant , James Fleet , Simon Callow , John Hannah , Kristin Scott Thomas , David Bower

Runtime
117 minutes

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

Andrew Lincoln holding a sign that says,

Love Actually

The 2003 romantic comedy Love Actually follows various couples as they explore their relationships throughout the Christmas season. With a star-studded cast composed of Bill Nighy, Colin Firth, Alan Rickman, Emma Thompson, Keira Knightley, Hugh Grant, Laura Linney, Liam Neeson, Rowan Atkinson, Chiwetel Ejiofor, Martin Freeman, and Martine McCutcheon, Love Actually has since become a Christmas staple for rom-com lovers.

Director
Richard Curtis

Release Date
November 14, 2003

Runtime
135 minutes

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

Bridget Jones's Diary Bridget

Bridget Jones’s Diary

Based on the novel by Helen Fielding, the rom-com Bridget Jones’s Diary revolves around a 32-year-old single woman who keeps a diary of her life and romantic encounters. Starring Renée Zellweger, Colin Firth, and Hugh Grant, the 2001 movie was a massive commercial and critical success.

Director
Sharon Maguire

Release Date
April 13, 2001

Cast
Renee Zellweger , Gemma Jones , Celia Imrie , James Faulkner , Jim Broadbent , Colin Firth

Runtime
97 Minutes

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.

In 2022, Bridget Jones author Helen Fielding revealed that a fourth movie in the series, based on her book Mad About the Boy, was in the works (via Radio Times.)

2 10 Things I Hate About You (1999)

Directed by Gil Junger

A promo still featuring the cast of 10 Things I Hate About You.

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. 

Director
Gil Junger

Release Date
March 31, 1999

Cast
Julia Stiles , Heath Ledger , Joseph Gordon-Levitt , Larisa Oleynik , Larry Miller , Andrew Keegan , David Krumholtz , Susan May Pratt

Runtime
97 minutes

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

When Harry Met Sally

Written by Nora Ephron and directed by Rob Reiner, When Harry Met Sally chronicles the life and relationship of Harry Burns and Sally Allbright, who meet just after college on a road trip to New York City and begin a decade-long relationship that slowly evolves from friendship to true love. Billy Crystal and Meg Ryan star as Harry and Sally, with a further cast that includes Carrie Fisher and Bruno Kirby. 

Director
Rob Reiner

Release Date
July 21, 1989

Cast
Bruno Kirby , Meg Ryan , Carrie Fisher , Steven Ford , Billy Crystal

Runtime
95 minutes

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



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