Who's Your Caddy? is the latest entry in the storied "white people are like this, black people are like that" comedy subgenre. Like, you know how white people hang out in snooty country clubs and listen to classical music, while black people love to smoke weed and dance to the latest hip-hop jams? The filmmakers behind Who's Your Caddy? totally noticed that, too. The tired racial stereotypes that Caddy inserts into the old Caddyshack-style "slobs vs. snobs" formula should probably make it much more offensive than it is. But it's too good-natured—thanks mainly to charismatic star Antwan "Big Boi" Patton—and it's too anachronistic to be taken all that seriously. (Aren't country clubs more sexist than racist these days?)
Patton plays a rapper scheming to gain membership at the club where his late father once worked as a caddy. Standing in his way is well-traveled character actor Jeffrey Jones, stuck in the thankless "crusty college dean" role as a country-club owner. Jones enlists improbably foxy lawyer Tamala Jones to keep Patton off his course, but when she inevitably falls for Patton's smooth-talkin', mama-lovin' ways, her psychotically racist boss hires a crazy midget (played by crazy-midget-for-hire Tony Cox) to kill him. When that fails, the two square off in a climactic game that accurately portrays the prevalence of farting in golf.
Most of the comedy in Who's Your Caddy? comes courtesy of the bumbling Jones (essentially playing a variation on his signature role as Principal Rooney in Ferris Bueller's Day Off) and Patton's entourage of wacky thugs, including Faizon Love, the source of that golfing flatulence. Meanwhile, Patton seems to be starring in an entirely different movie. Whenever he and Tamala Jones start flirting, it's a charming glimpse at the pleasant little romantic comedy Who's Your Caddy? might have been, had the rest of movie let them play out the back nine alone.