12. Frank Sinatra
Frank Sinatra was fairly heavily investigated by the police and authorities. In 1998, the FBI released a 1,300 page file on the entertainer, explaining that they had concerns regarding his possible connections to organised crime. It also revealed at one point that Sinatra even offered to become an FBI informer which begs the question, he must have felt the information he had would have been useful. But before all this, in 1938 Sinatra was actually arrested. On November 26, 1938, he was arrested in Hackensack, New Jersey on a charge of Seduction. Yes. Seduction. This was dismissed as it was discovered that the woman was married. Then less than a month later on December 22, he was re-arrested on a charge of Adultery for the same offence. Boy, Sinatra can pick his offences can't he? This was eventually dismissed as well. Despite everything else that the FBI had on him, he was never re-arrested for anything relevant and his only prison time was related to being held on over nights prior to being bailed for the Seduction/Adultery charges.