Date: March 5, 1998
In 1996, Sacramento rapper C-Bo was sent to Soledad State Prison for two years for his role in a gang-related fight that occurred two years earlier. When released, the conditions of his probation required that he not be allowed to record music that promoted the "gang lifestyle" or was "anti-law enforcement."
C-Bo's 1998 release Til My Casket Drops, was, of course, full of gangbanging references, and so the rapper was put back in jail. The story attracted national attention, and he was ultimately freed, as the terms of his probation were clear First Amendment violations.