Long before his rise to Rat Pack fame, Frank Sinatra found himself on the wrong side of the law. In 1938, at just 23 years old, he was arrested by the sheriff of Bergen County, New Jersey, on charges of “seduction”—a now-obsolete crime tied to having relations with a woman of “good repute” under the promise of marriage. When it was later revealed the woman was married, the charge was changed to adultery. Ultimately, both charges were dismissed. The incident remains one of the more bizarre footnotes in the crooner’s legendary career.