Humphrey Bogart and Lauren Bacall in The Big Sleep (1946)
Age difference: 25 years
You can’t really go wrong with a movie directed by Howard Hawks, adapted by William Faulkner from a novel by Raymond Chandler, and starring Humphrey Bogart and Lauren Bacall. The comically complicated plot is candy for mystery lovers, but those who prefer a good love affair won’t be disappointed by the slowly developing romance between Bogart’s hardboiled detective and the mysterious daughter of a rich man (Bacall).
James Mason and Sue Lyon in Lolita (1962)
Age difference: 37 years
We would never call James Mason and Sue Lyon’s romance in Lolita “good” in the sense that a middle-aged man having sex with a middle-school girl is in any way morally defensible. But Stanley Kubrick’s film adaptation of the classic Vladimir Nabokov novel was far from cheap (in fact, the sexual content was toned down to satisfy censors); it rendered the relationship between Lolita and Humbert Humbert in a way that didn’t endorse or condemn the characters but merely depicted their plight. At two and a half hours long, the rambling roadtrip of a film perfectly illustrated Humbert’s isolation and hopelessness in the face of his desires.
Ruth Gordon and Bud Cort in Harold and Maude (1971)
Age difference: 52.5 years
There have been other older woman/younger man May-December romances on film, but none is quite as compelling as Harold and Maude. (Fun fact: Anne Bancroft, who famously portrayed Mrs. Robinson, the seductive mother of Dustin Hoffman’s fiancée inThe Graduate, is only six years older than Hoffman in real life.) Hal Ashby’s dark comedy introduces us to an 80-year-old woman and 20-year-old man whose complementary quirks make them better suited to one another than most couples who were born in the same decade. Unfortunately, though, love doesn’t always conquer all.
Marlon Brando and Maria Schneider in Last Tango in Paris (1972)
Age difference: 28 years
Bernardo Bertolucci’s epic mindfuck of a magnum opus gave us one of cinema’s most disturbing sex scenes (you’ll never look at butter the same way again). But, as with Lolita, the love affair between Brando’s lonely, angry, American widower and Schneider’s fresh, young, engaged French woman is anything but schlock. A tale of power and trust, innocence and corruption, and the lure of anonymous, boundary-pushing sex in the face of boring commitment, Last Tango in Paris is a journey into Freudian chaos.
Woody Allen and Mariel Hemingway in Manhattan (1979)
Age difference: 26 years
Mariel Hemingway was only 17 years old when Manhattan came out. In fact, she recently told W the following story about playing Allen’s high school-aged girlfriend: “My first real make-out session in my life was with Woody in a hansom cab in front of a camera crew. Before the scene, I practiced making out on my arm in front of the mirror. After we had done the scene once, I said to the cinematographer, Gordon Willis, ‘We don’t have to do that again, do we?'” Despite that shudder-inducing tale (not to mention the unfortunate echoes of Allen’s real love life), it’s clear that the confusing lawlessness of modern romance — and his idealization of her youth — are what draw them to each other.
Harry Dean Stanton and Nastassja Kinski in Paris, Texas (1984)
Age difference: 24.5 years
The generation separating Stanton’s Travis Henderson from his wife Jane (Nastassja Kinski) isn’t the focus of Paris, Texas. But it does add an extra layer of confusion to the Sam Shepard-penned, Wim Wenders-directed mystery of amnesiac Travis’s struggle to rebuild his life after being lost and presumed dead for four years.
Jack Nicholson and Helen Hunt in As Good as It Gets (1997)
Age difference: 26 years
In the role that established the late-career, pricky-old-man persona he still maintains, Nicholson plays a nutty, misanthropic author who allows a waitress and single mother (Hunt) to slowly melt his glacial heart. This is probably the least believable relationship on the list, but Nicholson is always fun to watch, and there’s a cute kid involved, so we’ll make a rare exception to our general feel-good Oscar bait aversion.
Steve Buscemi and Thora Birch in Ghost World (2001)
Age difference: 24 years
Sometimes, it isn’t the older guy who holds all the power in a May-December relationship. Consider Birch’s Enid Coleslaw, who befriends geeky record connoisseur Seymour (Buscemi) out of a combination of boredom and guilt over having played a mean joke on him. In her jealousy and need to be desired, Enid ruins Seymour’s one true shot at a healthy relationship — and then takes the rest of his life along for the ride.
Bill Murray and Scarlett Johansson in Lost in Translation (2003)
Age difference: 34 years
Like Last Tango in Paris, Lost in Translation concerns a forbidden romance between a middle-aged man and a young woman in a committed relationship. But that’s where the similarities end. While Bertolucci’s movie is taut and intense, Sofia Coppola’s drifts languidly through Tokyo. It isn’t animal attraction that drives the relationship between Murray’s Bob and Johansson’s Charlotte; it’s their shared aimlessness and disorientation.
Sean Penn and James Franco in Milk (2008)
Age difference: 18 years
This true story of a gay rights pioneer begins on Harvey Milk’s (Penn) 40th birthday, when he meets Franco’s Scott Smith. Then in his early 20s, Scott provides the closeted actuary with the opportunity to change his life. Together, they move to San Francisco, where Harvey becomes a local politician and activist. Their relationship doesn’t survive (and neither does Harvey, tragically), but it’s clear that without Scott’s influence, Harvey would never have had the courage to change the world.