December 1953: Marilyn Monroe
Marilyn Monroe was flat broke when, in 1949, she posed nude for photographer Tom Kelley for fifty bucks. Kelley didn't get much more for the pictures when he sold them to the Western Lithograph Company, which offered the image on a calendar.
Meanwhile, Monroe's career flourished: 1950 saw the release of The Asphalt Jungle and All About Eve, and she was on her way. Hugh Hefner obtained the image (titled "Golden Dreams") for his magazine's first centerfold, which was called "Sweetheart of the Month" rather than Playmate. Although the picture wasn't new, its appearance in the magazine created a stir, as by 1953 she had cracked the "Quigley Poll of the Top Ten Money Making Stars."
20th Century Fox, Monroe's Employer, fretted about what to do when the scandal broke. Monroe came up with the solution: She gave an interview in which she admitted she was broke and needed the money to make rent. People bought it, and Monroe won sympathy from the public. It's a wonder this shocking strategy of telling the truth is so rarely used.