3. Bruce Bowen
Years Played: 1997-2009
Team(s): Heat, Celtics, 76ers, Spurs
Stats: 6.1 PPG, 2.8 RPG, 1.2 APG, 2.2 PFPG
How did an undrafted guard carve out a successful 14-year career for himself? Hard work and determination, right? Well, maybe some of that, but it's undeniable that Bruce Bowen built his career on low blows and an entire arsenal of dirty plays. Widely regarded as one of the dirtiest players in league history, he now graces the set of ESPN with bow ties. His defense was instrumental in winning three championships with the Spurs.