The Age Gaps Between Romantic Leads In These 17 Movies From The ’90s Will Shock You

Table of Contents Recently, a tweet about the age gap between Laura Dern and Sam…

The Age Gaps Between Romantic Leads In These 17 Movies From The ’90s Will Shock You

The ’90s were clearly a different time.

Recently, a tweet about the age gap between Laura Dern and Sam Neill in Jurassic Park went kinda viral.

Roxane Gay / Via Twitter: @rgay

And it got me wondering – how large were the age gaps between romantic leads in some of our other favorite ’90s movies? Check out our findings below!


My Best Friend’s Wedding (1997)

Tristar Pictures / Via Everett Collection

In My Best Friend’s Wedding, Michael and Kimmy, the couple that Julianne (played by Julia Roberts) hopes to come between, were nearly a decade apart in age in real life. 

Michael was played by Dermot Mulroney who was 34 at the time of the film’s release, and Kimmy was played by Cameron Diaz, who was 25.


You’ve Got Mail (1998)

Warner Bros / Via Everett Collection

Before Joe Fox (Tom Hanks) gets with Kathleen Kelly (Meg Ryan) in You’ve Got Mail, he’s dating Patricia Eden, played by the inimitable Parker Posey. 

In real life, the pair had a fairly steep age gap. Tom Hanks was 42 at the time, while Parker Posey was just 29.


Casino (1995)

Universal / Via Everett Collection

The intense Vegas-set crime drama, Casino, finds the beautiful Ginger (Sharon Stone) married to mobster Sam “Ace” Rothstein (Robert Deniro) and having an affair with his associate, Nicky Santoro (Joe Pesci). 

In real life, both men were quite a bit older than Sharon Stone, who was 37 at the time: Robert De Niro was 51 and Joe Pesci was 52. 


As Good As It Gets (1997)

Sony Pictures / Via Everett Collection

The 1997 rom-com As Good As It Gets follows cynical and rude romance writer Melvin Udall, who falls for the sweet waitress at the diner he eats breakfast at every day. 

Melvin was played by Jack Nicholson, who was 60 years old at the time. Helen Hunt, who plays the kind waitress Carol Connelly, was much younger at just 34 years old.


Pretty Woman (1990)

Buena Vista Pictures / Via Everett Collection

In the infamous rom-com Pretty Woman, Julia Roberts plays Vivian, a sex worker who is picked up by Edward, a handsome businessman played by Richard Gere, forming an unlikely but undeniable connection. 

In real life, Julia Roberts was just 22 at the time of the film’s release, while her leading man, Richard Gere, was 40 years old.


Runaway Bride (1999)

Paramount / Via Everett Collection

Julia Roberts and Richard Gere starred opposite each other in another romance a few years later: Runaway Bride. Roberts plays the infamous Maggie Carpenter, known for leaving three grooms at the altar, and Gere plays Ike Graham, a reporter who writes about her checkered past and eventually falls for her.

In 1999, their 18-year age gap was still steep, but maybe less stark considering Julia Roberts was no longer in her 20s. She was 31, and Richard Gere was 49 years old.


While You Were Sleeping (1995)

Buena Vista Pictures / Via Everett Collection

While You Were Sleeping is the favorite of many rom-com lovers who were charmed by Sandra Bullock’s performance as the lonely, hopeless romantic Lucy, who falls for her crush’s brother Jack (Bill Pullman) in the midst of a messy case of mistaken identity. 

Sandra Bullock was just 30 at the time, while her lover, played by Bill Pullman, was 41 years old.


Poison Ivy (1992)

Ronald Grant Archive / Mary Evans / Via Everett Collection

Another film with an intentional age gap, Poison Ivy is a sinister story about Ivy (Drew Barrymore), a disenchanted teenage girl who, craving the stability of a family, tries to forge her way into her best friend’s family by seducing her father, Darryl (Tom Skerritt). 

While the age gap was intended, it’s not clear if it really needed to be a 41-year age gap. In 1992, Tom Skerritt was 58 years old, while Drew Barrymore was only 17.


He Got Game (1998)

Walt Disney Co. / Via Everett Collection

In the 1998 sports drama He Got Game, Denzel Washington plays Jake Shuttlesworth, the father of the most sought after high school basketball prospect, Jesus Shuttlesworth. He’s also just been paroled from jail for accidentally killing his wife, and his relationship with his son is rocky, so he stays in a rundown motel, where he meets and romances Dakota Barns, a troubled woman played by Milla Jovovich.   

In real life, Denzel was 43 years old at the time of the film’s release, while Milla Jovovich was just 22.


Six Days, Seven Nights (1998)

Bruce McBroom / © Buena Vista / Via Everett Collection

Anne Heche plays the business-minded magazine editor Robin Monroe in Six Days, Seven Nights, opposite the unpredictable cargo pilot Quinn Harris, played by Harrison Ford. The duo find that despite their differences, they have a spark that can’t be ignored. 

Another thing that can’t be ignored? The actors’ age difference. Harrison Ford was 55, while Anne Heche was a whopping 26 years younger at 29.


In the Line of Fire (1993)

Bruce McBroom / ©Columbia Picture / Via Everett Collection

The 1993 political thriller, In the Line of Fire, featured a romance between Secret Service agent Frank Horrigan (Clint Eastwood) and Secret Service agent Lilly Raines (Rene Russo). 

In real life, Clint Eastwood was 63 at the time, and Rene Russo was 39 years old, making for a 24-year age gap.


Entrapment (1999)

20th Century Fox / Via Everett Collection

The 1999 heist film Entrapment stars Catherine Zeta-Jones as Virginia “Gin” Baker, an insurance investigator going undercover to catch suspected art thief Robert “Mac” Macdougal, played by Sean Connery. As her web of lies grows, so does the pair’s relationship. 

But the real-life age gap was really quite inappropriate. Catherine Zeta-Jones was a young 28 at the time of filming, while Sean Connery, who was well into his career, was 67 years old, making for a 39-year age gap.


Indecent Proposal (1993)

Paramount / ©Paramount/Courtesy Everett Collection / Via Everett Collection

The 1993 film Indecent Proposal is about, well, an indecent proposal, made by mysterious billionaire John Gage, who offers a million dollars to sleep with Diana Murphy, a real estate agent whose finances have recently taken a hit. Despite her being happily married, Gage successfully woos her.

John Gage was played by Robert Redford, who was 56 at the time, and Diana is played by Demi Moore, who was much younger at 30 years old.


A Perfect Murder (1998)

Warner Bros / Via Everett Collection

The age difference between the romantic leads in A Perfect Murder is not a coincidence. Emily (Gwyneth Paltrow) is written to be the young wife of the older Wall Street businessman Steven (Michael Douglas).

In 1998, Michael Douglas was 54 years old, more than twice the age of Gwyneth Paltrow, who was 26 at the time. 


Bulworth (1998)

20th Century Fox / Via Everett Collection

The 1998 political satire Bulworth finds Jay Bulworth, a disillusioned politician played by Warren Beatty, ready to end it all — but with the help of someone else, so that his family can collect his insurance policy. But he begins to reconsider his plans when he finds himself falling for the young and beautiful Nina, played by Halle Berry.

In real life, Warren Beatty was 61 years old at the time of the film’s release, while Halle Berry was 30 years younger at 31.


Little Women (1994)

Joseph Lederer / ©Columbia Pictures / Via Everett Collection

The 1994 adaptation of Little Women, which stars Winona Ryder as Jo March, features a relationship between Jo and Friedrich Bhaer, an older professor played by Gabriel Byrne. 

In real life, Winona Ryder was 22, and Gabriel Byrne was twice her age at 44 years old.


How Stella Got Her Groove Back (1998)

20th Century Fox / Via Everett Collection

Technically, How Stella Got Her Groove Back is about an older woman falling for a younger man, so the age gap isn’t exactly surprising. In fact, the age gap between the actors is actually smaller than the 20-year age gap between the characters they play: Stella is 40, and Winston is 20.

Angela Bassett was 39 at the time of film’s release, while her leading man, Taye Diggs was 27.

Which age gap shocked you the most? Let us know in the comments!