A 19-year old Morrison was arrested in 1963 for drunkenness and for the Bertie Woosterish theft of a policeman’s hat.
In 1938, a 23-year-old Sinatra was arrested on charges of ‘seduction’ and ‘adultery’. His initial charge stated that: 'On the second and ninth days of November 1938 at the Borough of Lodi' and 'under the promise of marriage' Sinatra 'did then and there have sexual intercourse with the said complainant, who was then and there a single female of good repute.' Sinatra was released on $1,500 bond, but when it was determined that the lady in question was married a complaint of adultery was substituted, with Sinatra's bond being lowered to $500. That charge, too, was dismissed, and neither crime exists today.
In May 1947 the jazz legend, then 32, was locked up for eight months on a drug conviction.
Bowie, then 29, was arrested along with Iggy Pop in upstate New York in March 1976 on a cannabis possession charge following a concert. He was held for a few hours then released. His mugshot is as cool as hell, isn’t it, but it was taken a few days after the arrest when he appeared in court for arraignment.