Who: Singer Frank Sinatra.
When: In 1938, in Bergen County, New Jersey.
Why: This happened at a time when it was illegal to engage in sexual conduct with a woman of high-standing reputation.
At first, Sinatra was arrested and booked for Seduction, of “a reputable woman” but it was later determined the woman involved was married, so the charge was revised slightly. Sinatra was again arrested, this time for Adultery.
Outcome: The 23-year-old promptly paid his bond and was released. The Adultery charge was later dropped. He only spent a few hours in jail as a result of the situation.