4. Kenny Smith
Years In The Booth: 1998-Present
Lesser known for his playing days, TNT's Kenny Smith has built himself a nice career on the network with Inside the NBA. Often the straight man to Charles' goofy routine, Kenny and Ernie help hold it all together. He's not the star of the show (more on that later), but he definitely holds his own. Mostly by mentioning his rings every chance he gets.