The Graduate (1967)

Director Mike Nichols raised May-December relationships to mythic status with the Oscar-nominated flick The Graduate (1967). The celebrated romantic dramedy follows Benjamin Braddock (Dustin Hoffman), a recent college graduate who doesn’t know what to do with his life. Everyone’s got advice for him, like “plastics” — but Ben’s more concerned with rubbers! How else can he safely bang his neighbor’s middle-aged wife Mrs. Robinson (Anne Bancroft)? Even though Ms. Bancroft was really only 35-years-old during the shoot, audiences know she’s a cougar by her leopard-print bra. The sexy stunner also shows off her cleavage via a white brassiere. No wonder, Ben’s secretly having a ball with her. Yet things get complicated when his parents pressure him to date her daughter Elaine (Katharine Ross). In an effort to nip this new relationship in the bud, Benjamin takes her to a strip club. It’s no fun for Elaine, but it’s a joy for us since we get to see a be-thonged dancer (Lainie Miller) shake her tassel-clad rack! Despite his initial reluctance, Ben realizes Elaine’s “the one” and decides to court her. As you can guess, Mrs. Robinson is against the union and tries to break them up. While on this quest, we are treated to views of her body double’s nude boobs! Of course, Benjamin is the real boob. As such, Elaine decides to marry another. But when Ben crashes the wedding ceremony before she says, “I do”, he wonders what to do. They may not have a happy ending, but you will!