It was long before Ol' Blue Eyes would become an international icon, but Frank Sinatra was arrested in 1938 on charges of adultery and seduction. Yes, they used to be able to arrest people and charge them with seduction, something that faced a 23-year-old Frank Sinatra. The seduction charge against Frank Sinatra on November 26th, 1938 was dismissed, but the 'Chairman of the Board' was arrested again on December 22nd, 1938, for adultery. What exactly did Frank Sinatra do to warrant as tough a charge as seduction? In the borough of Lodi, Frank Sinatra was accused of having sexual intercourse with a single female who was formerly in good repute, something that was apparently against the law at the time.
The second charge against Frank Sinatra was actually just a revision of the first charge. The woman, supposedly of good repute, turned out to be married. After the first charges of seduction against Frank Sinatra, the legendary singer was released on $1,500 bond, but the complaint was dismissed less than a month later and a charge of adultery was put in its place. The bond for Frank Sinatra was set at $500, which he paid and was released to continue his seductive ways. The charge of adultery was later dismissed. Where Frank Sinatra would go from that mugshot to decades of popularity and influence on the world of music was hard to say, but that shot from his early-20s is still legendary, behind bars all over the world as a testament to the 'bad boy' reputation of a singer who appealed to every generation. All in all, Frank Sinatra only spent sixteen hours in jail and the worst thing he was ever arrested for was sleeping with a married woman, but the mugshot of Sinatra lives on in infamy.