1. Charles Barkley
Years in the Booth: 2000-Present
Nobody entertains fans more than Charles Barkley. Since his start at TNT back in 2000, he's been blessing us with gems in the form of brutally honest quotes about the game, and hilarious high jinx with the gang that puts the cherry on top. He's been a part of more dumb contests than we can name, but we've loved every second of it. Thank you, Sir Charles.