Lainie Miller in The Graduate (1967)

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Director Mike Nichols made a star of Dustin Hoffman and raised May-December relationships to mythic status in The Graduate (1967). A recent college graduate, Benjamin doesn't want to think about the future. Everyone's got advice for Ben, like "plastics." But what concerns Ben are rubbers, like the kind he uses with the neighbor's wife, Mrs. Robinson (Anne Bancroft). Ben's having a literal ball with Mrs. Robinson until his parents force him to go out with her daughter Elaine (Katharine Ross). Ben winds up falling in love with her, because, well, he's got a penis! But old lady Robinson doesn't want her daughter peeing in Mommy's dating pool, and she tries to bust them up. When Elaine finds out that her mom is all about the Benjamins, she runs back to college in a huff. Then Ben finds out Elaine is about to get married and heads for the church to bust up the wedding. Luckily Dustin's nose gets there two minutes before him and saves the day. Well, sort of.