'90s Team(s): Philadelphia 76ers (1990-92), Phoenix Suns (1992-96), Houston Rockets (1996-99)
Charles has become the most recognizable analyst in the NBA today. And for good reason because, unlike many in a mundane cliche infested industry, he's actually entertaining to listen to. The Emmy winner has frequently teased that he'd be retiring from broadcasting "soon" to run for political office between DUI arrests. Never change, Chuck!