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Movies With An Older Woman-Younger Man Romance

Norma Desmond (Gloria Swanson) is a terrifying vision of an older woman. She's a washed-up silent film star who ensnares a screenwriter (William Holden) and leads him to a fatal demise. Sunset Boulevard is a wonderful movie, but Norma both embodies and represents how Hollywood sees older women. Once past their prime, they are grotesque.

No name is more synonymous with these relationships than Mrs. Robinson. Anne Bancroft is dead sexy as the iconic character who seduces Dustin Hoffman’s aimless Benjamin Braddock. But, like Norma before her, Mrs. Robinson also turns vicious as she tries to keep Benjamin from her daughter Elaine (Katharine Ross).

The age gap gets even wider in Hal Ashby's classic. The bizarre tale is about the romance between a wild-child 79-year-old (Ruth Gordon) and a young man (Bud Cort) who stages suicides. They both like going to funerals. So much about this relationship could be off-putting, but it's ultimately sweet.

Jonathan (Andrew McCarthy) is an awkward prep school student. At a bar, he meets a gorgeous older woman, Ellen (Jacqueline Bisset), who surprisingly takes an interest in him. They start an affair, but it’s cut short when she realizes he lied about his age. They’ll meet again: Turns out, the woman is the mother of his BFF, Skip (Rob Lowe). Then the movie takes an icky turn. By its end, Ellen's checked herself into the hospital for psychiatric treatment, while Jonathan and Skip have had it out and made up. You see, bro friendship is more important than a woman’s mental health.

Susan Sarandon has two lovers in this baseball movie, in which she plays the older woman as hot sage. One is the more age-appropriate Kevin Costner, the world-weary minor-league catcher; the other is Tim Robbins, the upstart pitcher. (Robbins and Sarandon, who were married for more than 20 years, met on this film.)

Yes, Susan Sarandon’s in this one, too, but it’s Geena Davis’ Thelma who gets it on with a studly Brad Pitt in one of his very early roles. Thelma isn’t that much older than J.D., but her tryst with him shows her reclaiming her desires after she is sexually assaulted earlier in the movie. Unfortunately, J.D. turns out to be a grifter.

Angela Bassett plays the workaholic Stella, a single mother. She takes a trip to Jamaica and gets hit on by Taye Diggs’ Winston Shakespeare. (That name! Those abs!) Stella is conflicted over his age and faces the judgment of her friends back home.

Ah, yes, Stifler’s mom. Jennifer Coolidge's horny American Pie creation sleeps with Eddie Kaye Thomas' Finch. She is purely an object of teen male fantasy.

In Alfonso Cuaron’s film, Luisa (Maribel Verdu) hooks up with not one, but two sex-crazed younger men (Diego Luna and Gael Garcia Bernal). She goes on a road trip with them after finding out her husband has cheated on her. Throughout the entire trip, the audience ultimately learns, she's grappling with the notion that she's dying of cancer.

A mid-Friends Jennifer Aniston starred in this indie as Justine, a depressed 30-year-old retail clerk. Saddled with an unhappy marriage, Justine engages in an affair with new employee Holden (Jake Gyllenhaal). This is yet another example of the trope in which an older woman uses a younger man to revitalize her spirit. But tragedy is in the cards for these two.

This Sundance hit features a mature-for-his-age 15-year-old who really wants to get with his stepmother (Sigourney Weaver), but first ends up with his stepmother's friend (Bebe Neuwirth). Basically, if a teenager is the type who name-drops Voltaire, middle-aged ladies will be all over him.

Nancy Meyers' rom com features both an older man-younger woman relationship and an older woman-younger man relationship. At the outset, Jack Nicholson romances Amanda Peet, who plays Diane Keaton’s daughter. Then Keanu Reeves romances Keaton. The movie, however, preaches that age-appropriate love interests are best: Keaton and Nicholson are the characters you want to be together — when you’re not ogling the gorgeous Hamptons interiors.

Kate Winslet won her Oscar for her role as Hanna Schmitz, who has an affair with a 15-year-old (David Kross) in the late 1950s. She asks her younger lover to read to her. But she has many secrets. She was a concentration camp guard and is illiterate.

The plot of this movie is ridiculous enough to elicit giggles. Robin Wright and Naomi Watts are two smokin’ Australian moms, who each have an affair with the other’s equally smokin’ son.

Typically, the older party is seen as a predator. Nightcrawler flips that switch. Jake Gyllenhaal’s exceedingly creepy Lou Bloom blackmails local news director Nina Romina (Rene Russo) into sleeping with him. In another movie, it would be Russo’s character sweet-talking Gyllenhaal’s, but Nightcrawler makes him the sinister, amoral leech.

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