12 Great Older Woman, Younger Man Movies and Shows

Enjoy the fun of these May–December pairings, from ‘The Graduate’ to ‘Vladimir’

Thom Geier,

Updated April 08, 2026

AARP

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Published May 01, 2024

/ Updated April 08, 2026

rachel weisz and leo woodall in a scene from vladimir

Rachel Weisz embarks on a May/December romance with academic colleague Leo Woodall in "Vladimir" on Netflix.

Courtesy Netflix

Hollywood is notorious for casting male stars with romantic partners who are decades younger — remember when a then-68-year-old Sean Connery cavorted with a 29-year-old Catherine Zeta-Jones in the 1999 film Entrapment? But what about when the studios flip the May–December script and depict older women wooing younger men? The results can be surprising, sexy and even tragic. From Rachel Weisz’s 2026 Netflix series Vladimir back to the classic 1950 film Sunset Boulevard, here’s a look at some of the best — and most famous — shows and movies with an older woman, younger man plot.

Sunset Boulevard (1950, NR)

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 51-year-old Gloria Swanson) 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

All That Heaven Allows (1955, NR)

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 (who was only eight years younger than Wyman at the time). 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

The Graduate (1967, PG)

Here’s to you, Mrs. Robinson, queen of the cougars! When recent college grad Benjamin Braddock (Dustin Hoffman, now 88) 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. Despite being only six years older than Hoffman in real life, Bancroft 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 of the late 1960s.

Watch it: The Graduate

Harold and Maude (1971, PG)

There’s no mystery why Hal Ashby’s cult film flopped when it first opened: Audiences could not wrap their heads around a romance between a spirited septuagenarian (Ruth Gordon) and a death-obsessed 20-year-old (Bud Cort). But the quirky film has since earned cult status, placing No. 9 on the American Film Institute’s 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

Bull Durham (1988, R)

Susan Sarandon, now 79, plays a sexually self-aware baseball groupie who makes it a point to take one player from the local Durham Bulls under her wing (and into her bed) each season. She soon finds herself torn between hot-shot rookie Tim Robbins, now 67 (who would become Sarandon’s real-life partner for two decades, despite a 12-year age gap), and wizened journeyman Kevin Costner, now 71. 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

Thelma & Louise (1991, R)

Sarandon plays the titular Louise, but it's Thelma (Gina Davis, now 70) who has a fling with a handsome young drifter (Brad Pitt, now 62) in Ridley Scott’s classic women-on-the-lam road movie. 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 her savings).

Watch it: Thelma & Louise

How Stella Got Her Groove Back (1998, R)

Angela Bassett, now 67, plays a career-driven single mother who seriously needs a break. When she joins pal Whoopi Goldberg, 70, on a vacation to Jamaica, she catches the eye of a chef’s assistant (Taye Diggs, 55) who’s half her age. Romance blossoms, but so do complications. Luckily, it all ends in a mad dash to the airport to intercept Stella's true love before he becomes the one that got away.

Watch it: How Stella Got Her Groove Back

Good Luck to You, Leo Grande (2022, R)

Emma Thompson, 66, picked up a Golden Globe nomination for this comedy about a retired school teacher who resolves to change up her life after the death of a plain-vanilla husband who never once gave her an orgasm. She hires Leo Grande (Daryl McCormack), a young sex worker 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

May December (2023, R)

Director Todd Haynes’s award-winning drama looks at the unsettling aftermath of a scandalous relationship clearly inspired by the case of Mary Kay Letourneau and her teenage student. Julianne Moore, 65, stars as a teacher who at age 36 seduced a seventh-grade boy, now grown and living a mostly content life as her husband (played by 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 tabloid-fodder history.

Watch it: May December

The Idea of You (2024, R)

Anne Hathaway plays a divorcée in her 40s who starts an affair with a much younger man (Nicholas Galitzine) who also happens to be the lead singer in her teenage daughter’s favorite boy band. The sometimes steamy romance also digs into the challenging reality faced by a couple separated by decades of experience.

Watch it: The Idea of You

Dying for Sex (2025)

After a diagnosis of inoperable breast cancer, Molly (Michelle Williams), the 40-something heroine of this eight-part miniseries, decides to dump her well-meaning but distant husband of 15 years (Jay Duplass) and pursue a kind of sexual bucket list. Her quest for her first orgasm leads to dozens of hookups, most with much younger men she meets online. Williams nails the tricky tonal balance here, delivering a performance that’s sexy and funny and vulnerable and tragic — sometimes all at once.

Watch it: Dying for Sex

Vladimir (2026)

When a tenured English professor (Rachel Weisz, 56) learns that her fellow professor husband (John Slattery, 63) has been suspended for sleeping with students, she finds herself suddenly drawn to a hot and flirty young academic (Leo Woodall). Turns out he’s also married to another academic (Jessica Henwick), who’s gunning for tenure in the English department. Talk about complicated. Julia May Jonas adapted her own 2022 debut novel over eight episodes, retaining much of the sexiness, black comedy and insights into the double standards in romantic relationships.

Watch it: Vladimir

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Thom Geier is an AARP contributor and the award-winning former executive editor of TheWrap, senior editor at Entertainment Weekly, film reporter at The Hollywood Reporter and associate editor at U.S. News & World Report.

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