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Movies with the Biggest Age Gaps Between Leading Couples

May-December relationships aren’t all that uncommon in society, though they do seem to happen in movies a little more. In this video we’re taking a look at the largest age gaps between two stars of a movie, and telling you a bit about the films they starred in together! So stay tuned, as Facts Verse presents: Movies with the Biggest Age Gaps Between Leading Couples!

Harold and Maude – 52 year gap

There are some who call Harold and Maude the greatest romance story of the modern era. It’s a story about young Harold Chasen, played by Bud Cort, who is obsessed with death. So much so, that he goes to funerals of strangers, acts out fake suicides, and even drives a hearse. At one funeral, he meets the eccentric Maude, played by Ruth Gordon. Despite having a massive age gap, (Cort was 23 and Gordon was 75) the two characters have a similar hobby. And yet, personality-wise, they differ greatly. While Harold is dark and pessimistic about the world, Maude sees things with rose colored glasses. And, as is often the case, their opposite takes on the world make them best of friends. Over the course of their friendship, Maude teaches Harold a lot about life, including her love of art and culture. She even teaches him to play banjo.  Eventually, their friendship turns into romance. We won’t spoil the ending, but let’s just say it’s heart wrenching and uplifting at the same time. Theirs is the perhaps the ultimate May-December romance, and is held up as the paragon for unlikely romances in films. The 1971 movie has had a cult following for years, and was chosen to be in the National Film Registry. It was even ranked the 45th funniest movie of all time by AFI in 2000.

Venus – 50 year gap

Director Roger Mitchell released the film Venus in 2006, starring screen legend Peter O’Toole. O’Toole was 74 at the time, and would pass away seven years later. Acting opposite him was Jodie Whittaker, who was 24. Whittaker has gone on to great success in the industry, perhaps most notably as the 13th person to play the Doctor in the acclaimed series, Doctor Who. O’Toole plays Maurice, a former actor who finds himself alone at the end of his life. He’s fighting a losing battle to prostate cancer, and doesn’t have anyone in his life with whom to share his love of art. He then meets and falls for his friend’s grand-niece, Jessie. The two strike up an odd relationship, that, over the course of the movie, is shown to be a little manipulative. It seems that Jessie is essentially using Maurice for things like presents, and the use of his apartment to sleep with another man. Maurice, on the other hand, is open about his infatuation with Jessie. Though at this point in his life, he’s impotent, so their relationship is limited no matter what. At one point the two have a nasty fight, and Maurice is accidentally injured. But he doesn’t recall what happened, and asks for Jessie to be by his side to nurse him back to health. It’s a complex relationship between the two characters, who have a huge age gap between then. O’Toole’s performance in Venus garnered him his 8th nomination for Best Actor.

The Quiet American – 49 year gap

The Quiet American is a movie starring Michael Caine and Do Thi Hai Yen. At the time of filming, the two were 69 and 20 years old, respectively. That put their age gap at a hefty 49 years apart. The movie is a remake of a 1958 movie, and both movies were adapted from a bestselling novel from 1955 by Graham Greene. The Quiet American takes place in Vietnam at the culmination of the First Indochina War, which lasted from 1946 to 1954. It’s about a love triangle among an older man, Thomas Fowler, a slightly younger man, Alden Pyle, and a young woman named Phuong. In addition to Michael Caine and Do Thi Hai Yen, the movie also features Brendan Fraser as Alden Pyle. But in addition to being a love story, it’s also a movie about American politics and involvement in Vietnam that were a part of the build up of the Vietnam War years later. Fowler is a reporter covering the Indochina War, while Pyle is a CIA operative who was assigned an operation in Vietnam to promote American interests. Along the way, Pyle attempts to steal Fowler’s Vietnamese mistress, Phuong. The movie is a compelling mix of romantic intrigue, set against an intense background of government and sociopolitical change. Another interesting note was that it debuted on September 10th, 2001. After tanking at the box office because of the attacks of September 11th, as well as being criticized for being unpatriotic, it was shelved for a year. It was then released at the Toronto Film Festival in September of 2002 to stellar reviews.

The Big Lebowski – 45 year gap

The Big Lebowski is a slightly indefinable film, in that it spans a few different genres. But this cult classic has enjoyed classic status among modern-day movies, regardless of how its defined. Many see it as a crime drama, that’s also a noir film, but also a dark comedy. It stars Jeff Bridges as “The Dude” and has a stellar cast that includes legends like John Goodman, Steve Buscemi, Julianne Moore, and John Turturro. But it also includes a romance between two characters, played by David Huddleston and Tara Reid. The two actors were 68 and 23 years old at the time of filming, making that age gap 45 years. The film is ultimately a story spawning from mistaken identity, since the main character is named Jeffrey Lebowski, as is the character played by Huddleston. Bridges’ Lebowski is referred to as “The Dude” while Huddleston’s character is referred to as “The Big Lebowski.” After The Dude is mistaken for The Big Lebowski by some goons, who beat him up, he sets out on a mission to clear his name. The Big Lebowski informs The Dude that his wife, Bunny, has been kidnapped. He asks The Dude to act as the drop off man for a random hand off. Things go haywire, and the rest of the movie involves a bunch of madcap stories and bizarre characters whose stories often intersect. The film was written and directed by The Coen Brothers, and they even admitted that the story was intended to be a mystery that gets muddied by a lot of unimportant plot elements. It’s a hilarious and quirky movie that should really be seen several times.

Beginners – 43 year gap

Beginners is a lovely and poignant story about a man struggling to find love, as he remembers the final years of his father’s life. Even Mcgregor plays Hal, a man who is in a new relationship with a French woman, Anna, played by Melanie Laurent. In a series of flashbacks, Hal recollects the recent passing of his father, and the last portion of his life. His father, played by Christopher Plummer, had spent the majority of his life married to Hal’s mother. But after she died, Hal discovered that not only was his parents’ marriage a platonic one, but that his father was gay. It was only after Hal’s mother died that his father was able to come out of the closet, and enjoy his last few years as an openly gay man. During those years, he struck up a relationship with a man named Andy, who is much younger than he is. Andy is played by Goran Višnjić. At the time of filming, he was 38, while Plummer was 81, making their age gap 43 years. Beginners is a charming and heartfelt movie that explores sexuality, grief, and self identity. It won a slew of awards, including Best Feature at the Gotham Awards, and a nomination for Best Film and Best Directing at the Independent Spirit Awards. Plummer was also regaled with awards, including a BAFTA, a Golden Globe, a Screen Actors Guild Award, and an Oscar for Best Actor.

Poison Ivy – 42 year gap

Poison Ivy is an intense erotic thriller from 1992 starring Tom Skerritt, Sara Gilbert, and Drew Barrymore. It follows the story of a young, rich girl named Sylvie (played by Gilbert) who meets a girl from the streets and befriends her. But throughout the movie, that girl – Ivy, played by Barrymore, essentially cons her way into Sylvie’s family. She seduces Sylvie’s dad, played by Tom Skerritt, and eventually murders her mom. She also tries to frame Sylvie for a car accident. It’s a chaotic and dramatic movie, and the relationship between Skerritt and Barrymore drives the conflict throughout. At the time of filming, Skerritt was 59, and Barrymore was 17, which made for a 42 year age gap. And while it was selected for the Sundance Film Festival, it splot audiences. The NY Times said that at the festival, moviegoers were “either enraptured or insulted.” It’s overall critical reviews reflect that sentiment, as it has a 51% on Metacritic, and 41% on Rotten Tomatoes. Entertainment Weekly put Ivy as sixth on their collection of the top “bad girls” of all time.

Whatever Works- 40 year gap

Whatever Works is a Woody Allen film, where Larry David was given the task of playing the main character that usually is portrayed by Allen himself. As such, David’s character has many of the quirks and idiosyncratic views of the world that are often displayed by Woody. David plays Boris, a downtrodden man with OCD tendencies who has retired from his job as a Columbia professor. He avoids people and is generally condescending to them when he does interact with them. However, one day a girl named Melody shows up at his doorstep. She’s played by Evan Rachel Wood, and at the time of filming she was 22 while David was 62, giving them a 40 year age gap. Over the course of the movie, they develop a romance. At one point, Melody’s parents show up, revealing that they thought she’d been kidnapped. The movie follows the relationship of Boris and Melody as they both change (and not always for the better.) It was met with moderately good reviews, and has 50% on Rotten Tomatoes.

Now it’s time to hear from you. Did you see any of these movies? Did the age gap make it feel awkward to watch? Let us know in the comments section below!

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