Throughout Hollywood history, there are several examples of movies about couples made up of people who were wildly different in their ages that have succeeded on virtually every level. For example, films like Lost in Translation, The Graduate, Rear Window, and Something’s Gotta Give all featured May December relationships and were celebrated by the masses.
For every film that did a great job addressing couples with huge age gaps between them, there are many others that fail in that regard. Whether that means ignoring the differences in how old the characters are or addressing them in a tasteless way, some film couples were a major turn off. With that in mind, it is time to get to this list of 15 movie couples whose age differences were hard to accept.
15 Clint Eastwood and Rene Russo - In the Line of Fire
Released in 1993, if you ask us, In the Line of Fire is one of the tensest movies of Clint Eastwood’s career, and that is really saying something. Unfortunately, the one area in which the film fell apart to a large degree is its romance storyline.
After all, Eastwood who was 63 at the time and looking every bit of that age was playing a character who dated someone portrayed by Rene Russo who was 24 years younger than him since she was 39.
14 Mariel Hemingway and Woody Allen - Manhattan
Among the most celebrated films of all-time, Manhattan was even included on the American Film Institute’s list of the best comedy films and their countdown of the highest quality romance movies.
Starring and directed by Woody Allen who was 42 at the time, in the film he dated a character played by a then 16-year-old Mariel Hemingway, which meant there was 26 years between them.
13 Anne Heche and Harrison Ford - Six Days, Seven Nights
Of all the movie couples on this list, it could be argued that Anne Heche and Harrison Ford from Six Days, Seven Nights had the least amount of chemistry. It is very likely that part of the reason why they seemed to lack any connection is there was a 26 age gap between them, as he was 55 at the time and she was 29.
12 Jeff Bridges And Maggie Gyllenhaal - Crazy Heart
Certainly, a highly successful film, Jeff Bridges won an Oscar for his work in Crazy Heart and Maggie Gyllenhaal was nominated as well which is proof that both were excellent in the movie. However, there was something truly odd about seeing Bridges who was 58 at the time and Gyllenhaal who was 31, start-up an onscreen romance.
11 Dudley Moore and Nastassja Kinski - Unfaithfully Yours
Considered to be a comedy superstar at one time, these days it seems like the younger generation has absolutely no idea who Dudley Moore even is, which is a shame. Not one of his better movies, when Dudley Moore filmed Unfaithfully Yours he was 50 which meant there was a 27 year age gap between him and the actor who played his wife, Nastassja Kinski, who was 23.
10 Kelly LeBrock and Gene Wilder - The Woman in Red
While Gene Wilder is best known for films like Willy Wonka & The Chocolate Factory in which he was quite youthful, by the time he filmed The Woman in Red he was 51 and he looked even older. That is why it was so off-putting to see him portray someone who gets involved with a character played by Kelly LeBrock, an actor who was 24 at that time and very vivacious.
9 Emma Stone and Colin Firth - Magic in the Moonlight
Given how beloved Emma Stone and Colin Firth are, you’d think more people would remember that they played characters who got involved with one another in a Woody Allen film. Despite that, it seems to be completely forgotten that when Firth was 53 and Stone was 25 they were a couple in Allen’s Magic in the Moonlight together which meant there was a 28 year age gap between them.
8 Sean Penn and Emma Stone - Gangster Squad
From one entry that involves Emma Stone to another, this time around we are looking at her role in the movie Gangster Squad in which her character has a romance with Sean Penn. With Stone 25 at the time and Penn 54, he was 29 years older than she was. That said, Penn looked older than he was back then so it felt like the disparity in their ages was even more severe.
7 Michael Keaton and Andrea Riseborough - Birdman
Easily one of the most experimental modern movies that received mainstream success, Birdman was shot to look like it was all captured in one take which made it stand out. However, there was nothing unusual about it featuring a character played by a then 60-year-old Michael Keaton, date a younger woman who was portrayed by Andrea Riseborough who was 30.
6 Scarlett Johansson and Billy Bob Thornton - The Man Who Wasn’t There
Of all the movie couples on this list, it could be this one from the Coen Brothers’ movie The Man Who Wasn’t There that is the hardest to even fathom in real-life. Yet, in that film, Scarlett Johansson who was 16 at the time portrayed a character who tried to seduce the person Bill Bob Thornton played even though there was a 30 year age difference between them.
5 Olivia Wilde and Liam Neeson - Third Person
Due to the fact that the 2013 movie Third Person made just over one million dollars at the box office, it is safe to assume that many moviegoers have no idea it exists. In that case, they’d also not know that Olivia Wilde who was 29 played someone who had an onscreen fling with Liam Neeson’s character even though he was 61.
4 Woody Allen and Mira Sorvino - Mighty Aphrodite
Evidently not content with playing a character who dated someone 26 years his junior in Manhattan, when Woody Allen cast his film Mighty Aphrodite, he cast Mira Sorvino as his love interest. Considering that Allen was 60-years-old at that time and Sorvino was 28, and it could be argued that he looked older than he was, them playing a movie couple was pretty gross.
3 Michael Caine and Michelle Johnson - Blame It on Rio
In a lot of ways, it blows our minds that Blame It on Rio exists as one of its stars, Michelle Johnson, had to get permission from a court to film certain scenes as she was only 17 at the time. After permission was granted, Johnson took on the role of a teen who has an affair with a man who was 33 years older as her romantic interest was played by a then 50-year-old Michael Caine.
2 Sean Connery and Catherine Zeta-Jones - Entrapment
Long considered to be a Hollywood legend, by the time Sean Connery starred in the movie Entrapment when he was 69 many of his past on-screen romantic interests had been much younger than him. Still, it was pretty wild that Connery’s character in that film had a connection with someone played by Catherine Zeta-Jones who was 30 back then, which means he was 39 years older than her.
1 Tom Skerritt and Drew Barrymore - Poison Ivy
Already a Hollywood veteran by the time she starred in Poison Ivy, when Drew Barrymore took on her lead role in that film she was only 17 years of age. On the other hand, the grown man her character seduced in that film was portrayed by a man who was 42 years older than her since Tom Skerritt was 59 when this film was in production.