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Sunset Boulevard (1950)
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.
The Graduate (1967)
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).
Harold and Maude (1971)
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.
Bull Durham (1988)
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.)