Lil Wayne
Even Weezy did a bid. Back in 2010 Lil Wayne landed in jail in New York on drug and weapons possession charges. He did his time and got out early for good behavior.
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Slick Rick
Slick Rick shocked fans when he shot his cousin and former bodyguard and an innocent bystander in 1990. It turns out that this cousin had tried to have him shot previously. Legal troubles including deportation followed him after that mishap.