Jamal "Shyne" Barrow

Bad Boy recording artist Shyne sold more than 500,000 copies of his debut album before he was sent off to serve his 10-year prison sentence for his involvement in an altercation at Club New York on December 27, 1999. Barrow was convicted of assault charges, reckless endangerment and criminal possession of a gun. The Sean "P. Diddy" Combs protege is expected to serve eight years and seven months of his sentence.