18. Stephen Jackson
High School: Oak Hill Academy (Mouth of Wilson, VA)
Accomplishments: 1x NBA Champion
Teams: Nets, Spurs, Pacers, Warriors, Bobcats, Bucks
Career Stats: 15.7 PPG, 4.0 RPG, 3.2 APG, 1.3 SPG
Stephen Jackson has had quite a few fails in his 12-year career, like breaking ground in new ways to injure oneself and some of his raps. But Jackson has been about that life (and that life) for a while. He has averaged double figures throughout the majority of his career and even has a ring. How many swag rappers can boast about that?