Charles Barkley

Sport: NBA
Years: 1984-2000
Never at a loss for words, the Round Mound of Rebound first made waves politically by supporting the first president Bush in the 1992 election (he famously quipped "My family got all over me because they said Bush is only for the rich people. Then I reminded them, 'Hey, I'm rich'."). He's toyed with the idea of running for governor of his native Alabama on multiple occasions, filmed a video in support of Barack Obama in 2007, and officially changed his registration to Independent in the 2000s.