Haters like to say that gangster rap is so authenticity-obsessed that nothing could be better for a street rapper than a jail sentence. This is only true up to a point. Shyne's debut album was, in retrospect, pretty solid front-to-back. The Barrington Levy assisted singles "Bad Boyz" and "Bonnie and Clyde" were both fire, and album cuts like the Whodini-sampling "It's OK" have dated surprisingly well. The main thing that jammed up his rap career, though, was going to jail for a decade after a shooting incident involving Puff Daddy. Another way to sideline your rap career is being deported the second after you're freed.
Go To Jail For a Long, Long Time (Or Multiple Times)