The Cougar and the Sugar Daddy; sounds like the title of one of those seedy '80s adult film that you’d randomly find a VHS of on the top shelf at a newsagent, poorly-stocked convenience store, or knock-off Blockbuster… “Knockbuster.” Regardless of their heritage being relatively recent, cougars and sugar daddies are universally understood terms, referring to an older man or woman who has romantic relations with someone significantly their junior.

“The Toyboy and the Gold Digger” alludes to the exact converse, and similarly resembles the name of a sordid Boogie Nights rip-off, starring a Dirk “Pigler." Hollywood's scriptwriters have frequently penned screenplays that detail 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 that concern a romantic age difference…

Charade

Charade Cary Grant and Audrey Hepburn
Universal Pictures

Cinema icons Cary Grant and Audrey Hepburn feature alongside each other in 1963’s romantic murder mystery, Charade. Starring as Peter Joshua and Regina Lampert, the pair work together to get to the bottom of the suspicious circumstances around her husband’s death. Walter Matthau also stars in this perfect little movie from Stanley Donen.

Harold and Maude

Harold and Maude in the love story movie
Paramount Pictures

1971’s cult classic, Harold and Maude, is an embodiment of H.H. Fowler’s “Love Knows No Bounds.” Hal Ashby's very dark comedy details the burgeoning romance between 20-year-old Harold (Bud Cort), a disenchanted and suicidal young man, and 80-year-old, Maude (Ruth Gordon), an outlandish elderly woman with a lust for life. Between the legendary Cat Stevens score and the incredible performances, Harold and Maude remains a classic, cult or otherwise.

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

Crazy Heart

Man sits on doorstep with guitar in Crazy Heart
Fox Searchlight Pictures

Scott Cooper’s 2009 movie 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 diminishing relevance has him travel up and down the states playing to anyone that will listen, from basement speakeasy bars to bowling alleys. With his health and career in decline, Blake encounters a music journalist, the single mother Jean (Maggie Gyllenhaal), who inspires him to get his life back on track, and they subsequently become romantically involved.

As Good as it Gets

Greg Kinnear, Helen Hunt and Jack Nicholson in a car in As Good as it Gets
Sony Pictures Releasing

Directed by James L. Brooks, and starring Jack Nicholson, 1997’s Oscar-winning As Good as it Gets is a feel-good romantic comedy that won The Shining actor his third Academy Award, and second for Best Actor. Playing the disgruntled, miserable, and malicious novelist Melvin Udall, who suffers from extreme OCD, Nicholson's character lives an isolated existence and alienates everyone who comes into contact with him.

An ultimate story of redemption and character reformation, As Good as it Gets 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

Lolita movie 1960s Kubrick
MGM

In Stanley Kubrick’s 1962 screen adaptation of the 1955 novel, Lolita, James Mason plays foreign professor Humbert Humbert, who moves in with a widow and her daughter in a New Hampshire suburb. Initially content with Charlotte, whom he marries, his attention very quickly turn to her 14-year-old daughter, Lolita (Sue Lyon) who he begins to creepily obsess over. A story of forbidden love, gross obsession, and utter manipulation, Lolita is an uncomfortable classic that confronts a controversial topic.

Licorice Pizza

The Two Leads of Licorice Pizza
Universal Pictures

In this hazy ‘70s romp, director Paul Thomas Anderson pits together Cooper Hoffman and Alana Haim for their respective feature-length debuts in 2021’s Licorice Pizza. Arguably the funniest movie of 2021, the coming-of-age comedy-drama tells the tale of precocious high school student, actor, and water-bed businessman, Gary Valentine (Hoffman) and the convoluted yet charming relationship he builds with a 25-year-old photographer assistant, Alana Kane (Alana Haim).

Related: Best Comedy Movies of 2022, Ranked

The Graduate

The Graduate with Mrs. Robinson in bed
United Artists

Post-pubescent adolescents have come to fetishize older women over the years. In 1967’s The Graduate, university student Ben Braddock (Dustin Hoffman) lives out many teenage boys’ fantasies when an older lady, Mrs. Robinson (Anne Bancroft), makes romantic advances. Stuck in a mental conflict over how to proceed, Ben has to decide whether to continue his affair with the wife of his father’s business partner or attempt to woo her daughter. With groundbreaking direction from Mike Nichols and a popular 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 profound adoration for his hometown of New York was brought to the silver screen in his 1979 rom-com, Manhattan. Allen stars as protagonist Isaac Davis, a man in the midst of an existential crisis, as his love life and career hit a crossroads.

After his wife leaves him for another woman, Isaac enters into a relationship with a high school girl, Tracy (Mariel Hemingway), yet soon finds his eye wandering. While it's a bit gross and ironic to consider the film in light of Allen's own life, it is a stunning portrait of the city and Allen's old ethos that "the heart wants what it wants."

Lost in Translation

Lost in Translation
Focus Features

Set against the backdrop of the 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 concerns the lives of Hollywood actor Bob Harris (Bill Murray) and a hotshot photographer's tag-along girlfriend, Charlotte (Scarlett Johansson), while on respective trips to Tokyo.

Having flown over to star in a Japanese Whiskey commercial, a reclusive Bob meets an isolated Charlotte, and the pair strike up a budding, if ambiguous, relationship despite the age gap of 34 years.

Singin’ in the Rain

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

Ranked 10th on the BFI’s 2022 Sight and Sound poll, 1951’s Singin’ in the Rain details an on-screen couple’s struggles to transition from Hollywood’s silent era to the “talkies.” As they try to adapt to the industry’s rapidly-changing climate, Don (Gene Kelly) takes to his new role swimmingly, but Lina (Jean Hagen) does not. Replaced by Kathy (Debbie Reynolds), Don becomes infatuated with his new co-star and falls deeply in love with her.