12 Classic Older Woman–Younger Man Movies to Watch After Michelle Williams' ‘Dying for Sex’

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

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

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