Lil Wayne

Rapper Lil Wayne performs during the America’s Most Wanted Music Festival at the MGM Grand Garden Arena on August 31, 2013 in Las Vegas, Nevada.
(Source: Ethan Miller/Getty Images North America)
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 attends the All Star Music Experience at Federal Ballroom on February 15, 2014 in New Orleans, Louisiana.
(Source: Aaron Davidson/Getty Images North America)
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.