8. Ray Allen (He Got Game & Harvard Man)
Ray Allen was cast in the Spike Lee film He Got Game and he did a serviceable job playing off an ensemble cast featuring a gang of veteran actors. He was noticeably better in his role in James Toback's 2001 film Harvard Man. Oddly enough, James Toback is the same man who cast Allan Houston in Black And White. Ray Allen's last acting job was when he pretended to be a Celtic for years before instead opting to join the Miami Heat after they offered him a deal for less money and fewer years.