The best movies with a romantic age difference

The Cougar and the Sugar Daddy; sounds like the title of one of those seedy 1980s adult movies you’d randomly find a VHS on the top shelf of a newsagent’s, poorly stocked convenience store, or counterfeit Blockbuster… “Knockbuster.” Despite their ancestry being relatively recent, cougars and sugar daddies are universally understood terms, referring to an older man or woman who is in a romantic relationship with someone significantly younger than them.


“The Toyboy and the Gold Digger” refers to the exact opposite, and similarly resembles the name of a villainous Boogie nights rip-off, starring a Dirk “Pigler”. Hollywood screenwriters have often written screenplays detailing stories of older men and women (but mostly men) falling in love with younger men and women (but mostly women). Let’s take a look at some of the best English-language movies about a romantic age difference…

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Puppet show

Charade movie starring Cary Grant and Audrey Hepburn
Universal images

Cinema icons Cary Grant and Audrey Hepburn star side-by-side in the 1963 romantic murder mystery, Puppet show. Starring Peter Joshua and Regina Lampert, the two team up to investigate the suspicious circumstances surrounding her husband’s death. Walter Matthau also stars in this picture-perfect Stanley Donen movie.

Harold and Maud

Harold and Maude in the love movie
Paramount Pictures

The cult classic from 1971, Harold and Maud, is an epitome of HH Fowler’s “Love Knows No Bounds.” Hal Ashby’s very dark comedy chronicles the budding romance between 20-year-old Harold (Bud Cort), a disillusioned and suicidal young man, and 80-year-old Maude (Ruth Gordon), a bizarre older woman with a zest for life. . Between the legendary Cat Stevens score and the incredible performances, Harold and Maud remains a classic, cult or otherwise.

Related: Harold and Maude 50 Years Later May Be the Best Love Story for People Who Hate Romantic Movies

Crazy heart

Man sits on the sidewalk with guitar in Crazy Heart
Fox Searchlight Photos

Scott Cooper’s 2009 movie Crazy heart, based on the novel of the same name by Thomas Cobb, tells the story of alcoholic country singer Bad Blake (Jeff Bridges), whose rapidly diminishing relevance sees him travel the states playing to anyone who will listen, from basement speakeasy bars to bowling alleys. With his health and career declining, Blake meets a music journalist, single mother Jean (Maggie Gyllenhaal), who inspires him to get his life back on track, and they subsequently become romantically involved.

As well as possible in the given circumstances

Greg Kinnear, Helen Hunt and Jack Nicholson in a car in As Good as it Gets
TriStar Photos

Directed by James L. Brooks, starring Jack Nicholson, 1997 Academy Award winner As well as possible in the given circumstances is a feel-good romantic comedy that won The shining actor his third Academy Award and second for Best Actor. Nicholson plays the disaffected, miserable and malevolent novelist Melvin Udall, who suffers from extreme OCD, and lives an isolated existence, alienating everyone who comes into contact with him.

An ultimate story of redemption and character transformation, As well as possible in the given circumstances plays host to an unlikely romance between middle-aged Melvin and young mother Carol Connelly (an Oscar-winning Helen Hunt), the waitress at his usual restaurant.

Lolita

1960s Lolita Movie Kubrick
MGM

In Stanley Kubrick’s 1962 film adaptation of the 1955 novel, Lolita, James Mason plays foreign professor Humbert Humbert, who moves in with a widow and her daughter in suburban New Hampshire. Initially pleased with Charlotte, whom he marries, his attention soon turns to her 14-year-old daughter, Lolita (Sue Lyon), for whom he becomes eerily obsessed. A story about forbidden love, gross obsession and total manipulation. Lolita is an awkward classic that confronts a controversial topic.

Liquorice pizza

The two main lines of liquorice pizza
Universal images

In this hazy 1970s romp, director Paul Thomas Anderson teams up Cooper Hoffman and Alana Haim for their feature film debut in 2021. Liquorice pizza. Arguably the funniest movie of 2021, this coming-of-age comedy-drama tells the story of precocious high school student, actor, and waterbed businessman Gary Valentine (Hoffman) and the complicated yet charming relationship he builds with a 25 year old photographer assistant, Alana Kane (Alana Haim).

See also: Best comedy movies of 2022, ranked

The graduate

The graduate with Mrs. Robinson in bed
United artists

Over the years, postpubescent adolescents have begun to fetishize older women. In 1967 The graduateUniversity student Ben Braddock (Dustin Hoffman) lives out the fantasies of many teenage boys when an elderly lady, Mrs. Robinson (Anne Bancroft), makes romantic advances. Ben is caught in a mental conflict over how to proceed and must decide whether to continue his affair with his father’s business partner’s wife or try to woo her daughter. With groundbreaking direction from Mike Nichols and a hit soundtrack from Simon & Garfunkel, The graduate is truly a defining film of the 1960s.

Manhattan

Woody Allen and Hemingway in the movie Manhattan
United artists

Woody Allen’s deep admiration for his hometown of New York was brought to the silver screen in his 1979 rom-com, Manhattan. Allen plays protagonist Isaac Davis, a man in the midst of an existential crisis, as his love life and career come to a crossroads.

After his wife leaves him for another woman, Isaac enters into a relationship with a high school girl, Tracy (Mariel Hemingway), but soon finds his gaze wandering. While it’s a bit crude and tongue-in-cheek to view the film in light of Allen’s own life, it’s a stunning portrayal of the city and Allen’s old ethos that “the heart wants what it wants.”

Lost in translation

Lost in translation
Focus features

Against the backdrop of the cooking grills, casino slot machines, empty hotel bars and bright lights of Tokyo, Sofia Coppola’s Lost in translation turns 20 this year. The film is about the lives of Hollywood actor Bob Harris (Bill Murray) and Charlotte (Scarlett Johansson), the traveling girlfriend of a well-known photographer, during respective trips to Tokyo.

A reclusive Bob is flown over to star in a Japanese Whiskey commercial, meets an isolated Charlotte, and the pair begin a budding, if ambiguous, relationship despite the 34-year age difference.

Sing in the rain

Gene Kelly in Singin' in the Rain, one of the greatest musicals of the 1950s
Loews Inc.

Ranked 10th on the BFI’s 2022 Sight and Sound poll, 1951’s Sing in the rain chronicles an on-screen couple’s struggle to transition from the silent era of Hollywood to the “talkies.” As they try to adapt to the rapidly changing climate of the industry, Don (Gene Kelly) takes on his new role like a man possessed, but Lina (Jean Hagen) doesn’t. Replaced by Kathy (Debbie Reynolds), Don falls in love with his new co-star and falls madly in love with her.

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