Who's Your Caddy? (2007)

Antwan Andre "Big Boi" Patton, also known as one half of OutKast, is a hip-hop bigwig who wants to hobnob with the hotshots at a Carolina country club. There's one big problem for Mr. Boi, though: the owner is a seriously snooty racist. So begins Who's Your Caddy? (2007), the story of one man's outrageous attempts to t-off the bluebloods by teeing off on their green. Big and his outrageous entourage—including Sherri Shephard as his assalicious assistant—stir up all sorts of trouble for super snob Jeffrey Jones (best known and hated as Principal Ed Rooney in Ferris Bueller's Day Off [1986]). Jeff's luscious lawyer, Tamala Jones, finally convinces him to accept Big . . . so that they can boot him out once he misbehaves. Keep an eye out for the great Garret Morris and the great (and tiny) Tony Cox in cameos.