From 1984 to 2014, the average age gap between lead actors in romantic movies was 4.5 years. Though we don’t have corresponding data, the age gap between characters in romantic films is likely similar. Not all characters fall into this category, however, and some sport staggering gaps in age. With this in mind, we took a look at, and cataloged, 10 movies with large age disparities in character couples. Excluded are characters under 18, which means films like Manhattan, Lolita, and The Reader aren’t included on this list.

Lost in Translation — ~ 25 years

52-year-old Bill Murray and 17-year-old Scarlett Johansson have a much larger age gap in this film than that of their characters, who are in their late 40s and mid-20s, respectively. Still, Bob and Charlotte are roughly 25 years apart in Lost in Translation. Their wildly different ages are counterbalanced by identical feelings of isolation, loneliness, and culture shock as two unhappily-married Americans meet by chance in Japan. Commiseration leads to conjugation but not copulation, as the only romance between the pair occurs during an impromptu goodbye on a crowded street. They hug, kiss, and Bob whispers something to Charlotte that is not subtitled and is therefore lost without translation.

Crazy Heart — ~ 25 years

It takes a crazy heart to fall for a 57-year-old washed up and washed out country singer, which is what journalist Jean Craddock (Maggie Gyllenhaal) does in this 2009 film. She’s in her early 30s, divorced, and with a four-year-old son, but she finds herself charmed by the old soul of Otis “Bad” Blake (Jeff Bridges). In Jean, Bad sees a reason to turn his life around. He revives his career, gets sober, and makes amends with his estranged son. However, a drunken misstep with Jean’s son leads to their break up. Although Jean chooses a safer route with a different guy, Bad credits her for saving his life and they end the film on good terms.

Last Tango in Paris — 25 years

This infamous 1972 film stars Marlon Brando as Paul, a 45-year-old American widower who has a lustful tryst with Jeanne, a 20-year-old Parisian woman played by Maria Schneider. A 25-year age gap is far from the most disturbing part of their relationship, however. There’s name concealment, stalking, forced entry, gunfire, and the infamous act that earned the film an X rating and traumatized Schneider for life.

Autumn in New York — 26 years

Autumn in New York takes place during a “May-December romance” between 48-year-old socialite Will Keane (Richard Gere) and 22-year-old free spirit Charlotte Fielding (Winona Ryder). The relationship is ill-fated because, paradoxically, its younger half suffers from a terminal illness. Despite Will’s best attempts, which include hiring a specialist to save Charlotte, his young love dies. The film still manages to end on a good note, thankfully, as their brief and poignant relationship inspires Will to prioritize love over desire.

Entrapment — 28 years

Like Lost in Translation, Entrapment‘s biggest age gap is between actors rather than characters. The 1999 crime caper stars 29-year-old Catherine Zeta-Jones as 32-year-old Virginia “Gin” Baker and 68-year-old Sean Connery as 60-year-old Robert “Mac” MacDougal. That’s a 39-year gap in real life and a 28-year gap in the movie. Surprisingly, it seems like age is the only tool not utilized by the pair of art thieves as they work to entrap one another.

A Single Man — 32 years

George Falconer (Colin Firth) is the eponymous single man in A Single Man, after losing the love of his life to a car accident eight months prior. Unable to continue his esteemed but empty existence, the 52-year-old college professor decides that this day will be his last. He goes about his business like usual, save for packing a gun in his briefcase. Thankfully, a sensual but not sexual encounter with a 20-year-old student (Nicholas Hoult) prevents him from using it, and allows George to meet his end in a far more peaceful manner.

Something’s Gotta Give — 34 years

The thrust of Something’s Gotta Give is that 63-year-old playboy Harry Sanborn (Jack Nicholson) only dates women under 30. At the beginning of the movie, he’s dating 29-year-old auctioneer Marin Klein (Amanda Peet) but, by the end of the film, he’s married to her 56-year-old mother Erica Barry (Diane Keaton) instead. We’ll leave out details about how he gets to that point of intra-familial age gap acceptability, and let viewers enjoy it for themselves.

Last Vegas — 39 years

Last Vegas concerns four seniors (Michael Douglas, Robert De Niro, Morgan Freeman, and Kevin Kline) who travel to Las Vegas for a bachelor party. Billy (Douglas) is set to enjoy his wedding just before he turns 70. The kicker? His his bride-to-be, Lisa (Bre Blair), is 31. While in Vegas, Billy meets Diana (Mary Steenburgen), a woman much closer to him in age. They fall in love, Billy calls off the wedding with Lisa, and he hitches his wagon to Diana instead. Similar to Something’s Gotta Give, Last Vegas is about a man who comes to terms with aging by replacing his fountain of youth girlfriend with a geyser of maturity wife.

Venus — ~ 55 years

Maurice Russell is almost as old as Venus herself in this 2006 movie. Played by legendary thespian Peter O’Toole, who was 73 at the time of filming, its hard to nail down the exact age of O’Toole’s Russell, who has been placed in his 70s and as old as 80 by various viewers. Regardless of exact numbers, the character is clearly elderly and his love interest, Jessie (Jodie Whittaker), is 18. She’s the wild grandniece of his best friend, but the pair form an odd-couple relationship that plays on his impotence and her promiscuity. For example, Maurice helps fulfill Jessie’s interest in nude modeling, after which he nicknames her “Venus” for Rokeby Venus, a painting of the titular goddess in the buff by Diego Velázquez. Their romance barely escapes innuendo but it still counts as one of the largest age gaps in film history.

Harold and Maude — 60 years

Now for not just the largest age gap between human lovers in film history (that we could find), but the most celebrated. In Harold and Maude, a 19-year-old man (Bud Court) and a 79-year-old woman (Ruth Gordon) cultivate a relationship as unlikely as it is touching. He’s a quirky nihilist and she’s an eccentric romantic, but she teaches him more about existentialism than he could have ever imagined. It’s an age gap movie about closing the gap between love and death.

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