Who's Your Caddy? (2007)

When "street smart" rapper Christopher "C-Note" Hawkins (Big Boi) applies for a membership to all-white Carolina Pines Country Club, the establishment's proprietors are hardly ready to oblige him. Unwilling to accept that the club views him as unfit for membership, C-Note purchases land that contains the 17th green - willing only to exchange the hole for a membership.

This sets the stage for an outrageous assault on the country club and its membership committee as C-Note and his fun-loving, streetwise crew disrupt the goings-on at the club with their irreverent attitudes and a back-and-forth prankfest. At one point, C-Note plans to shoot a music video on the club's land. That leads the Club President, Cummings (Jeffrey Jones), to offer a bribe to get him to stop, but all C-Note wants is a membership to the club. President Cummings then hires Shannon Williams (Tamala Jones), an uptight lawyer who graduated Harvard at the top of her class. She goes to Christopher's house, he refuses yet another attempt to bribe him to leave. As a last resort, she devises a plan to allow him to join the club then to record him violating the club's bylaws to kick him out while he is on the club's 4 week probationary period. On separate occasions, he is accused of landing a helicopter on the property, bringing a gun onto the golf course and driving recklessly on the way to the golf course. Eventually, all the charges are proven wrong and C-Note is officially made a member of the Carolina Pines Country Club.