10 Onscreen Romantic Partners with the Biggest Real-Life Age Gaps

It’s not unusual for actors to play characters that differ in age from themselves. The pattern of older men playing across from much younger women appears to have been a popular choice since the Golden Age of Hollywood and hasn’t stopped since then. Although sometimes an age difference is necessary for the plot of a film, in a lot of cases, there’s no logical reason for such a large age difference between leading actors. And some of these age gaps make up feel uncomfortable watching the film as if we are supposed to simply ignore it.

Whether necessary or not, here are 10 of the largest real-life age gaps between on-screen partners

Related: 10 Shocking Weight Transformations By Actors For Films

10 Gerard Butler & Emmy Rossum: Phantom of the Opera

The 2004 film adaptation of Andrew Lloyd Webber’s stage show saw then-17-year-old Emmy Rossum earn a Golden Globe nomination for her role opposite 33-year-old Gerard Butler. A 16-year age gap isn’t crazy, but since the leading lady was yet to turn 18, it makes the film a bit weird to watch.

The age difference of the leading couple could have been even greater if the original choice of lead, Hugh Jackman (35 at the time), wasn’t already committed to Van Helsing. Katie Holmes was an option for the role of Christine, as was Anne Hathaway. Both would’ve still left a notable age gap (Holmes was 25 at the time while Hathaway was 21) but not as significant as the final casting.^[1]

9 Gene Kelly & Debbie Reynolds: Singin’ in the Rain

Singin’ in the Rain was Debbie Reynolds’s first starring role—at only the age of 19—and would later be known as her highest-profile film. Alongside seasoned actors Gene Kelly and Donald O’Connor, it is now often considered the greatest musical film ever made.

Gene Kelly, who also directed and choreographed the film, was 40 when he played alongside teenage Reynolds. Despite being a grueling process, Reynolds later stated, “Singin’ in the Rain and childbirth were the two hardest things I ever had to do in my life.” She always had respect for her experienced scene partner and director, who she said “made me a star…[and] taught me how to dance and how to work hard and be dedicated.”^[2]

8 Bing Crosby & Rosemary Clooney: White Christmas

White Christmas was the most successful film of 1954 and the highest-grossing musical at that time. The legendary cast saw Bing Crosby and Danny Kaye play opposite on-screen sisters Rosemary Clooney and Vera-Ellen.

The success of the song “White Christmas,” originally from Holiday Inn back in 1942, led to the creation of White Christmas, with Crosby as the leading man once again. Clooney, only 26 at the time of filming, was only a year older than Marjorie Reynolds when she played Crosby’s leading lady in Holiday Inn 12 years before. Crosby, in comparison, was 51 in 1954, giving a 25-year age gap between him and Clooney. Interestingly, although Clooney played the elder of the two sisters, she was actually seven years younger than Vera-Ellen.^[3]

7 Humphrey Bogart & Lauren Bacall: To Have and Have Not

Lauren Bacall was a model prior to the film To Have and Have Not when the wife of the director Howard Hawks saw her on the cover of Harper’s Bazaar. After a screen test, the unknown actress had a contract. In the 19-year-old’s film debut, Bacall’s originally small role was revised into the leading lady of To Have and Have Not. The new star played opposite established actor Humphrey Bogart, who was 45 at the time.

Although the film was often compared to Casablanca in unfavorable terms, the film launched the career of Bacall, which would see her at minimum be nominated for an Academy Award, Golden Globe, Grammy, Emmy, and Tony. Bogart and Bacall went on to make three more movies together, including Key Largo in 1948. The 26-year age gap seemed to be no problem for the couple, who married in May 1945, seven months after the film’s release. It was Bogart’s third marriage. The pair had two children together and remained married until Bogart’s death in 1957.^[4]

6 Michael Douglas & Gwyneth Paltrow: A Perfect Murder

A remake of the 1958 Hitchcock classic Dial M for Murder, the 1998 film saw 53-year-old Michael Douglas opposite Gwyneth Paltrow, aged 25 at the time. The 28-year age gap is deliberate, a suggestive reason behind Paltrow’s character Emily’s affair with painter David. It’s hard to believe there are less than 30 years between the leading couple, with one critic stating, “Douglas looks every one of his 54 years and then some. Gwyneth Paltrow is 25 and could pass for much younger.”

Hitchcock’s original film also saw an age difference, although not so large. With a 22-year age gap, Ray Milland played retired tennis player Tony across from Grace Kelly’s socialite Margot. A Perfect Murder didn’t quite live up to its predecessor, with one critic noting the film “has inexplicably managed to eliminate almost everything worthwhile about Dial M for Murder, leaving behind the nearly-unwatchable wreckage of a would-be ’90s thriller.” Another acknowledged the age difference, stating that Douglas should “hang up his spurs when it comes to playing a romantic lead with women in their twenties.”^[5]

5 Fred Astaire & Audrey Hepburn: Funny Face

Another classic from the Golden Age of Hollywood, Funny Face saw the union of legends Fred Astaire and Audrey Hepburn. Although not a financial success at the time, it has since been regarded as a masterpiece. Despite being three decades younger than Astaire, 27-year-old Hepburn insisted on him as her leading man.

Astaire had previously announced his retirement in 1946 but returned to the cinema in 1948 in Easter Parade. However, it wasn’t until 1981, 24 years after Funny Face, that Astaire was in his final film, Ghost Story.^[6]

4 Sean Penn & Emma Stone: Gangster Squad

Looking at Stone’s filmography, it appears that she is a popular choice for directors to play opposite older men. This includes Magic in the Moonlight, playing opposite Colin Firth (53), Irrational Man with Joaquin Phoenix (40), and Birdman alongside Edward Norton (45). But it’s in Gangster Squad that we see Stone’s oldest on-screen partner.

Penn played gangster boss Mickey Cohen in the 2013 action thriller. At age 54, he was nearly 30 years older than 25-year-old Stone at the time of the film’s shooting. But it is perhaps that Penn appears older than he is that makes the on-screen couple so shocking to see. What hits harder is that Stone is only three years older than Penn’s own daughter, Dylan.^[7]

3 Liam Neeson & Olivia Wilde: Third Person

Unlike many films on this list, Third Person is a relatively unknown film, having had a limited release in 2014. Nevertheless, the cast list is fairly star-studded, including Mila Kunis, Adrien Brody, Kim Basinger, Olivia Wilde, and Liam Neeson.

It’s the latter two of these stars we see in an on-off romantic relationship. Here, 61-year-old Neeson plays Michael, who recently separated from his wife and remains involved with his lover, played by 29-year-old Wilde. Although a noticeable age gap is necessary for the plot, with 32 years between the on-screen couple, the desired effect could have still been achieved with a much smaller age difference. While the pair provide what is needed from them, unfortunately, the film was given negative reviews from critics and has a score of only 25% on Rotten Tomatoes.^[8]

2 Sean Connery & Catherine Zeta-Jones: Entrapment

As a former James Bond, Sean Connery was no strange to younger, beautiful on-screen romantic partners. But at the age of 68, Connery played opposite then-30-year-old Catherine Zeta-Jones in the 1999 heist film.

The nearly 40-year age gap between the two is never noted in the film, seemingly unimportant to the plot. Only seven years later, in 2006, Connery announced his retirement from acting, while Zeta-Jones has taken several breaks from the screen since the late 2000s. Obviously, this age gap didn’t bother Zeta-Jones as she married Michael Douglas, who is 25 years her senior.^[9]

1 James Mason & Sue Lyon: Lolita

Based on Vladimir Nabokov’s 1955 novel of the same name, the age difference in Lolita is the most disturbing—but also crucial to the plot of the film. With an age gap of 39 years, 53-year-old James Mason plays across Sue Lyon, who was only 14 at the start of filming.

In the unsettling plot involving hebephilia with Mason’s character Humbert and his stepdaughter, the film actually increased the age from the novel where the titular character is only 12. With the filming grossing $9.25 million (on a budget of $2 million) and Lyon winning a Golden Globe for her role, Lolita was undoubtedly a commercial success. There’s something about actually seeing the disturbing relationship on screen that makes the story all the more unsettling than simply reading it on the page of Nabokov’s novel. However, due to Lyon’s age, an of-age body double was used for the more explicit scenes—I would hope so!^[10]