Hollywood has always favored exceptionally young women. In film, male leads are frequently paired with much much much younger women. If you ask most women, it is creepy as all get out to see Leonardo DiCaprio with Margot Robbie or Bradley Cooper with Jennifer Lawrence. This is all in service to the male gaze and the fact that many men feel entitled to the attention and affection of younger women as they age.

It is also a flaw of Hollywood in that executives feel like male stars draw in audiences more than female stars do. That may have been true in the 1930s, 1940s, and 1950s when gender roles were stricter and more traditional, but newsflash, it is 2022, and gender roles are definitely more blurry and less traditional.

Recently, Hollywood has been better at casting romantic leads of similar ages, and romance movies starring women over 40 have been gradually popping up. In Marry Me, Jennifer Lopez and Owen Wilson are well-matched — both actors turn or have already turned 53 in 2022. In The Hating Game, Lucy Hale is 32 and just five years younger than her co-star, 37-year-old Austin Stowell. On the other hand, Paul Thomas Anderson’s Licorice Pizza reverses the trend, with 19-year-old Cooper Hoffman’s character falling for 30-year-old Alana Haim’s character.

The nine films below are all a bit older and feature some really creepy age differences between the romantic leads.

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9 Silver Linings Playbook — 15 Years

     The Weinstein Company

Silver Linings Playbook hit multiplexes across the country in 2021. Bradley Cooper played Pat Solitano, a man who has bipolar disorder and, at the start of the film, had just been released from eight months in a psychiatric institution. Jennifer Lawrence played Tiffany Maxwell, who agrees to help him get his wife back if he enters a dance competition with her, but they gradually begin a romance together. Cooper was 37 and Lawrence was 22 when this film came out.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

8 Wolf Of Wall Street — 16 Years

     Paramount Pictures

The Wolf Of Wall Street was released in 2013 and is based on the true story of Jordan Belfort, who defrauded investors in his company Stratton Oakmont. Olivia Wilde was interested in playing the love interest of DiCaprio’s Jordan Belfort in the film but was told she was too old for the role; she was 29-years-old. The role eventually went to then 23-year-old Margot Robbie, while DiCaprio was 39-years-old.

7 Edge Of Tomorrow – 20 Years

     Warner Bros. Pictures 

The 2014 action-science fiction film Edge Of Tomorrow starred Tom Cruise in his then latest attempt to prove he has the fitness levels and agility of a much younger man. This tale of aliens who invade Earth and take over Europe, necessitating an elite American defense Corp to rescue the continent, also starred Emily Blunt as Cruise’s semi-love interest. Blunt was 31-years-old at the time and Tom Cruise was 51-years-old.

6 As Good As It Gets – 26 Years

     Sony Pictures Releasing

In 1997’s As Good As It Gets, Jack Nicholson played a novelist with a number of drawbacks — he was homophobic and perpetually cranky, to name two of his distasteful maladies, and had crippling OCD. Helen Hunt played his waitress, a single mother whose son was chronically ill. Both Nicolson and Hunt won the Academy Award for Best Actor and Actress, respectively. At the time, Hunt was 34-years-old and Nicholson was 60-years-old.

5 Indecent Proposal – 26 Years

In 1993, Indecent Proposal (and Demi Moore’s iconic ’90s outfits, specifically that black dress) was making waves at the box office and around water coolers where people wondered: would you (or would you want your wife) to spend a night with someone else for $1 million? Moore’s onscreen husband was Woody Harrelson, who is just a year older than Moore. However, the man with whom they make the deal with, Robert Redford, was 56-years-old. His character wanted Demi because he felt entitled to her attention and affection. Demi Moore was 30-years-old at the time.

RELATED: 8 Actors Who Played Characters Beyond Their Age Range

4 Magic In The Moonlight – 28 Years

     Sony Pictures Classics

Magic In The Moonlight is a 2014 romantic comedy from the problematic Woody Allen. That’s all that really needs to be said to indicate there will be a massive and ridiculous age difference in the film, but this time it’s not between Allen and some ingénue, but between Colin Firth and Emma Stone. Now, let’s be honest, many women would give Colin Firth a pass for just about anything, but this casting is all on Allen. Firth was 53-years-old and Stone was 25-years-old.

3 Lost In Translation – 34 Years

     American ZoetropeElemental Films

One of the most egregious examples of a ridiculous age difference is in Sofia Coppola’s film, the 2003 romantic comedy Lost in Translation. Bill Murray starred as a has-been American movie star in the midst of a midlife crisis who travels to Tokyo to be a spokesperson for a whiskey brand. While there, he meets another displaced American, a recent college graduate played by Scarlett Johansson. Though it’s debatable whether the two had a romantic connection or more of a platonic one about friendship in the midst of their respective loneliness, it’s undeniably a bit creepy to see the 52-year-old Murray man running around with an 18-year-old Johansson.

2 Something’s Gotta Give – 35 Years

In 2003, Something’s Gotta Give hit two milestones. While it starred a female romantic lead over 40 in Diane Keaton, it also had a ridiculous age difference first, as Jack Nicholson’s character starts out the movie dating Keaton’s character’s young daughter, played by Amanda Peet. Nicholson’s character was a record company owner who prided himself on only dating women under 30, until he was forced to co-habitate with Keaton while recovering from a cardiac incident. Nicholson was 66 years old and Peet was 31-years-old.

1 Entrapment – 39 Years

     20th Century Fox

The award for the biggest age difference between romantic leads in a film goes to 1999’s Entrapment. Catherine Zeta-Jones played an investor for an insurance firm, and Sean Connery played a thief specializing in international art. Their paths crossed and sparks flew in this espionage thriller which, as we wrote in the Blu-ray review, “somehow makes us believe Catherine Zeta-Jones might sleep with Sean Connery.” Connery was 68-years-old and Zeta-Jones was 29-years-old. Then again, Zeta-Jones has been happily married to Michael Douglas sine 2000, who is 25 years older (77 to her 52), so to each their own.