#6: Frank Sinatra
Before becoming Chairman of the Board, Sinatra acquired one particularly embarrassing mug shot. In 1938, New Jersey authorities arrested the 23-year-old singer on a charge of “seduction,” then a criminal offense involving intercourse with an unmarried woman under a promise of marriage. When authorities discovered the woman was already married, the original charge was dismissed and replaced with adultery, which was also later dropped. Nothing came of the prosecution, but Sinatra entered superstardom with a police photograph already sitting in the archives.
