20. The United States v. Terrance Boykin (2009)
Crime: One Count of Bank Robbery, Violation of Federal Firearms Statutes
Sentence: Currently serving 10 years at Big Spring Federal Correctional Institute in Texas.
On January 4, 2007, a Chase Bank in Oak Park, Illinois, was robbed by two men at gunpoint, taking more than $100,000 in cash. Thanks in part to witness testimony and surveillance footage, police contended that Terrance Boykin, known to rap fans throughout the Midwest as Bump J, was one of the two culprits.
One of the most celebrated street rappers in Chicago hip-hop history, Bump J built steady buzz for both his music and the reputation of the Goon Squad, his heavily respected and feared crew. He had been signed to Atlantic Records, but his debut, which included production from Kanye West, was never released.
In November 2008, the rapper was arrested. To avoid a life sentence, Bump J took a plea deal that will keep him behind bars for 7 years. He should be out in 2015.