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12 Classic Older Woman–Younger Man Movies to Watch After Anne Hathaway’s ‘The Idea of You’

Here’s to you, Mrs. Robinson – and all the other Hollywood cougars out there

spinner image Anne Hathaway and Nicholas Galitzine walking together in a scene from The Idea of You
Anne Hathaway, right, and Nicholas Galitzine in "The Idea of You."

In the buzzy new Amazon Studios film The Idea of You, based on a best-selling novel by Robinne Lee, Anne Hathaway plays a 40-something divorcée who starts a torrid affair with a much younger man (Nicholas Galitzine of last summer’s gay rom-com Red, White and Royal Blue), who happens to be the lead singer in her teenage daughter’s favorite boy band. The sometimes steamy romance, which starts streaming May 2 on Prime, has earned rave reviews for its realistic depiction of an unlikely romance and the challenges facing a couple separated by decades of experience.

This isn’t the first time Hollywood has cast its gaze on older women wooing younger men on screen — though the reverse, male actors paired with actresses young enough to be their daughters, remains all too common.

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Here’s a look at some of the best — and most famous — depictions of big-screen cougars (and where to watch them).

Sunset Boulevard (1950)

In Billy Wilder’s noir classic, then 32-year-old William Holden plays a struggling Hollywood screenwriter who moves into the creepy mansion of an aging silent-film star (played by Gloria Swanson at 51!), who’s desperate to make a comeback in a Hollywood that’s long forgotten her. She maintains a magnetic hold over many, from her ex-husband turned manservant (Erich Von Stroheim) to Holden’s ever-pliable Joe, who all too quickly moves from punching up her screenplay to fluffing her bed pillows. When he tries to break off the relationship, though, things do not end well for him.

Watch it: Sunset Boulevard on Apple TV

All That Heaven Allows (1955)

Jane Wyman plays a wealthy widow who shocks her grown children and country club friends when she falls for her dreamy gardener, played by the ever-hunky Rock Hudson (eight years younger than Wyman). Director Douglas Sirk picks up every nuance of the suburban milieu, though he stacks the deck a bit with his choice of casting. Who wouldn’t fall for Rock Hudson?

Watch it: All That Heaven Allows, not streaming, DVD available on Amazon

The Graduate (1967)

Here’s to you, Mrs. Robinson, queen of the cougars! When recent college grad Benjamin Braddock (Dustin Hoffman) agrees to drive the wife of his dad’s law partner (Anne Bancroft) home from his graduation party, he doesn’t know what hit him. Bancroft, only six years older than Hoffman, invests Mrs. Robinson with a lusty energy that makes her the film’s most fascinating character. She’s arguably even more of a counterculture rebel, willing to defy societal norms, than the supposedly radical 20-somethings like Benjamin and her own daughter (Katharine Ross).

Watch it: The Graduate on Prime Video

Harold and Maude (1971)

There’s no mystery why Hal Ashby’s film flopped when it first opened: Audiences could not wrap their heads around a romance between a spirited septuagenarian (Ruth Gordon, 75) and a death-obsessed youth (Bud Cort, 20, who's now a year older than Gordon was in the film). The fact that The Godfather opened the same day probably didn’t help. But the quirky film earned cult status, placing ninth on the American Film Institute’s 2008 list of the best rom-coms of all time. And there’s something charming about a depressive young man who discovers joy in life only when he encounters a vivacious, much older woman who cherishes every last drop of it.

Watch it: Harold and Maude, available on Apple TV or Amazon

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Bull Durham (1988)

Susan Sarandon plays a sexually self-aware baseball groupie who makes it a point to take one player from the Durham Bulls under her wing (and into her bed) each season. She soon finds herself torn between hotshot rookie Tim Robbins (who would become Sarandon’s real-life partner for two decades, despite a 12-year age gap) and wizened journeyman Kevin Costner. In this one, the cougar meets her match with a guy who’s been around the bases a few times himself.

Watch it: Bull Durham on Prime Video

Thelma & Louise (1991)

Ridley Scott’s women-on-the-lam road movie is a classic for so many reasons — but one memorable element is the fling that Geena Davis’ Thelma has with a handsome young drifter played by Brad Pitt in his first major screen role. Davis is only about eight years older than Pitt, but the age difference adds an additional frisson to their scenes together — and helps you understand why her character might let her guard down (and allow Pitt’s grifter to sneak off with all of Thelma’s savings).

Watch it: Thelma & Louise on Prime Video

How Stella Got Her Groove Back (1998)

Angela Bassett plays a career-driven single mother who seriously needs a break. When she joins pal Whoopi Goldberg on a vacation to Jamaica, she catches the eye of a chef’s assistant (Taye Diggs) who’s half her age. (The actors themselves had a 14-year age difference.) Romance blossoms, but so do complications. Luckily, it all ends in a mad dash to the airport to intercept true love before it becomes the one that got away.

Watch it: How Stella Got Her Groove Back on Hulu

Notes on a Scandal (2006)

The catalyst for Richard Eyre’s award-winning drama is an illicit affair between a 30-something teacher (Cate Blanchett) and her 15-year-old student — but that scandal is just the tip of the iceberg. The real intrigue centers on Judi Dench’s parallel obsession with Blanchett, and the much older, very much closeted teacher’s elaborate efforts to manipulate the situation to her benefit.

Watch it: Notes on a Scandal on Max

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Don Jon (2013)

Sometimes it takes an older woman to help a younger man grow up. Joseph Gordon-Levitt plays a young lothario from suburban New Jersey whose relationship with a young woman (Scarlett Johansson) founders because real sex doesn’t match his copious experience with online porn. But then he strikes up an unlikely connection with a middle-aged community college classmate (Julianne Moore) that leads to intimacy both emotional and physical.

Watch it: Don Jon on Prime Video

Film Stars Don’t Die in Liverpool (2017)

In this bittersweet romance, Annette Bening plays a fading Hollywood starlet in the Gloria Swanson mold: the real-life Gloria Grahame, an Oscar winner for 1952’s The Bad and the Beautiful, who struck up an unlikely romance in her 50s with a young British actor (former Billy Elliot star Jamie Bell) nearly three decades her junior. The two share a genuinely passionate connection, one that’s complicated by her battle with breast cancer (and reluctance to seek treatment). Bening delivers a powerhouse performance that earned her an AARP Movies for Grownups Award.

Watch it: Film Stars Don’t Die in Liverpool on Max

Good Luck to You, Leo Grande (2022)

Emma Thompson picked up a Golden Globe nomination for this comedy about a retired schoolteacher who resolves to change up her life after the death of a plain-vanilla husband who never once gave her an orgasm. So she hires a 20-something sex worker named Leo Grande (Daryl McCormack) who gradually gets her to open up — not just to the joys of non-missionary sex, but also to the possibility of intimacy and living a full, rounded life at any age.

Watch it: Good Luck to You, Leo Grande on Hulu

May December (2023)

Director Todd Haynes’ award-winning drama looks at the unsettling aftermath of a scandalous older woman, younger man relationship. Julianne Moore stars as a teacher who at age 36 seduced a seventh grade boy, who’s now all grown up and living a mostly contented life as her husband (Riverdale alum Charles Melton). But the couple begin to reexamine their settled domesticity when a Hollywood actress (Natalie Portman) inserts herself into their lives as she preps for a splashy new role based on their tabloidy experiences.

Watch it: May December on Netflix

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