The best movies with a romantic age gap

The Cougar and the Sugar Daddy; sounds like the title of one of those seedy 80’s adult movies you happen to find a VHS of on the top shelf of a newsagent, a poorly stocked supermarket, or a fake blockbuster… “Knockbuster.” Despite the fact that their heritage is relatively new, cougars and sugar daddy’s are generic terms that refer to an older man or woman having romantic relationships with someone significantly younger.

“The Toyboy and the Gold Digger” alludes to the exact opposite, similarly resembling a dirty guy’s name boogie nights Rip-off starring a Dirk “Pigler”. Hollywood screenwriters have often created screenplays that describe stories of older men and women (but mostly men) falling in love with younger men and women (but mostly women). Let’s check out some of the best English language movies that involve a romantic age gap…



Charade film starring Cary Grant and Audrey Hepburn
Universal images

Cinema icons Cary Grant and Audrey Hepburn co-star in the 1963 romance crime thriller. farce. As Peter Joshua and Regina Lampert, the two work together to investigate the suspicious circumstances surrounding her husband’s death. Walter Matthau also stars in this perfect little film directed by Stanley Donen.

Harold and Maude

Harold and Maude in the romance film
Paramount Pictures

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

See also: Harold and Maude 50 Years Later might be the best love story for people who hate romance movies

crazy heart

Man sitting on the doorstep with a guitar in Crazy Heart
Fox Searchlight images

Scott Cooper’s 2009 film crazy heart, adapted from Thomas Cobb’s novel of the same name, tells the story of alcoholic country singer Bad Blake (Jeff Bridges) whose rapidly declining prominence leads him to travel up and down the States, playing from basement bars to whoever will listen to speakeasy bars bowling alleys. With his health and career in decline, 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.

It doesn’t get any better

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

Directed by James L. Brooks and starring Jack Nicholson, Oscar-winning 1997 film It doesn’t get any better is a feel-good romantic comedy that won The glow Actor his third Oscar and second for best actor. Playing the disgruntled, miserable and vicious writer Melvin Udall, who suffers from extreme OCD, Nicholson’s character lives an isolated existence and alienates everyone who comes in contact with him.

An ultimate story of redemption and character reform, It doesn’t get any better stars an unlikely romance between middle-aged Melvin and young mother Carol Connelly (an Oscar-winner Helen Hunt), the waitress at his usual restaurant.


Lolita Movie 1960 Kubrick

In Stanley Kubrick’s 1962 film adaptation of the 1955 novel lolita, James Mason plays Humbert Humbert, a foreign professor who moves in with a widow and daughter in suburban New Hampshire. Initially pleased with Charlotte, whom he marries, his attention quickly turns to her 14-year-old daughter, Lolita (Sue Lyon), with whom he is incredibly obsessed. A tale of forbidden love, gross obsession and utter manipulation, lolita is an uncomfortable classic that takes on a controversial subject.

Liquorice Pizza

The two leads of the licorice pizza
Universal images

In this hazy ’70s romp, director Paul Thomas Anderson brings Cooper Hoffman and Alana Haim together for their respective feature-length debuts in 2021 Liquorice Pizza. Arguably the funniest movie of 2021, the coming-of-age comedy-drama tells the story of precocious high school student, actor, and waterbed businessman Gary Valentine (Hoffman) and the twisted but charming relationship he has with a 25 year old builds up. year-old photographer’s assistant Alana Kane (Alana Haim).

Related: Best Comedy Movies of 2022, Ranked

The graduate

The graduate in bed with Mrs. Robinson
United artists

Post-adolescent adolescents have come to fetishize older women over the years. In the 1967s The graduate, college student Ben Braddock (Dustin Hoffman) is acting out the fantasies of many teenagers when an elderly lady, Mrs. Robinson (Anne Bancroft), makes romantic advances. In an emotional conflict over what to do next, Ben must decide whether to continue his affair with his father’s business partner’s wife or try to woo their daughter. Featuring groundbreaking direction by Mike Nichols and a well-loved soundtrack by Simon & Garfunkel, The graduate is truly a defining film of the 1960s.


Woody Allen and Hemingway in the movie Manhattan
United artists

Woody Allen’s deep devotion to his hometown of New York was brought to the big screen in his 1979 romantic comedy. Manhattan. Allen stars as protagonist Isaac Davis, a man in the midst of an existential crisis as his love life and career reach a crossroads.

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

Lost in translation

Lost in translation
focus functions

Against the backdrop of cook-it-yourself grills, casino slot machines, empty hotel bars and bright lights of Tokyo, Sofia Coppola’s Lost in translation turns 20 this year. The film follows the lives of Hollywood actor Bob Harris (Bill Murray) and Charlotte (Scarlett Johansson), the girlfriend of a high-profile photographer, as they each travel to Tokyo.

A reclusive Bob, who has flown over for a Japanese whiskey commercial, meets an isolated Charlotte, and the pair, despite their 34-year age difference, begin a burgeoning if ambiguous relationship.

sing in the rain

Gene Kelly in Singin' in the Rain, one of the best musicals of the 50's
Loew’s, Inc.

Ranked 10th in the BFI’s 2022 Sight and Sound Survey, 1951 sing in the rain describes a couple’s on-screen struggles to transition from Hollywood’s silent film era to the “talkies”. As they try to adapt to the rapidly changing climate of the industry, Don (Gene Kelly) embraces his new role with flying colors, but Lina (Jean Hagen) does not. Replaced by Kathy (Debbie Reynolds), Don falls in love with his new co-star and falls madly in love with her.