Perhaps the only rapper other than Pac to see jail “help” his career is Shyne. Jail time was swirling around his music before his debut album was even released. He signed to Sean “Diddy” Combs’ Bad Boy Records in 1999 and appeared on a couple of the label’s artists songs and remixes, immediately drawing comparisons to The Notorious B.I.G. because of his voice. But later that year he was involved in the infamous Manhattan club shooting where he allegedly opened fire in a club after someone threw money in Diddy’s face. He was subsequently charged with attempted murder, assault, and reckless endangerment. His self-titled debut album dropped in September 2000 and almost went platinum. But the celebration was short-lived as he was sentenced to 10 years in prison in July 2001. In 2004, after a bidding war between labels salivating to sell Shyne and his street cred, he reportedly signed with Def Jam Records for $3 Million. The album Godfather Buried Alive, was mostly recorded before he went to prison but featured one song recorded from behind bars. The album featured production from Kanye West, Swizz Beatz, Irv Gotti and Just Blaze and nearly went Gold, debuting at #1 on the Billboard Rap Charts. Shyne never released another album. He was freed in 2009 and deported to Belize. He has only released one mixtape, 2014’s Gangland, since.

Verdict: HELPED. Shyne defied Monopoly logic and collected $3 million dollars for GOING to jail.

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