C-Note (Big Boi), a rap superstar who is intensely bent on joining the elitist Carolina Pines Golf & Country Club, won't take no for an answer from Cummings (Jeffrey Jones), President of the swanky club's Powers That Be. So what's a rap divo to do? Call in his posse (Faizon Love, Tony Cox, Sherri Shepherd, Finesse Mitchell) to set things aright!
From blasting hard-thumping, thuggish rap jams on the golf course to one of the rap entourage's inability to control his flatulence in the men's room whilst standing next to one of the uber-stuffy Board members, C-Note's wild, loud crew succeed in their quest to make Cummings wish he was never born.
But Cummings has the perfect solution to fix C-Note's little red wagon: hire Shannon (Tamala Jones), a hard-nosed, attractive female attorney whose mission is to seductively bribe C-Note out of his steely determination to gain entry into Carolina Pines. However, Shannon finds her resolve weakening after she consults with C-Note, and eventually finds herself in his mother's (Jennifer Lewis) kitchen intent to learn more about her newfound love interest for reasons other than business.
We discover halfway through the film of the tender reason behind C-Note's reason for having a bone to pick with the Carolina Pines Golf & Country Club: C-Note's deceased father was once a caddy at the exclusive club and was prevented from advancing as a pro-golfer when his golfing skill became evident.
After C-Note and his cronies boldly compete in a golfing duel on the Carolina Pines golf course with Cummings, they win the club's membership by a landslide. Things will never be the same in the Carolina Pines neighborhood.
It doesn't take a genius to figure out that Who's Your Caddy? is a thinly-veiled, ghettofied remake of Caddyshack. The premise in too many Black comedies remains the same: it's us against them, so we're going to become a caricature of their worst impression of us. As the current urban slogan goes, we've got to do better. But wait, I forgot that the writers of this flick are non-Black.
The only character's name one recalls is C-Note's; everyone else's names and character personas only serve as the backdrop to this character's over-the-top ego. There was one redeemable factor in this movie, and that is Sherri Shepherd's random, totally improvised bit when she's speaking in tongues. I laughed about that part for days. The rest was exhausted stereotyping and ridiculous use of playing the race card. Pure tomfoolery.
All of this coming from "Our Stories" Films. It ain't my story, and it probably isn't yours.