It’d be very, very easy to write off Who’s Your Caddy? entirely. One of those comedies where black people smoke pot and direct rap videos while white people wear collared shirts and play golf, it’s little more than a vehicle for a lot of fart jokes, midget jokes and all kinds of slapstick humor. If you thought Caddyshack was too classy, this might be just what you were looking for.
So I can’t in good faith give Caddy a good review-- it feels overlong at 90 minutes, and is almost completely predictable-- but it’s not a total waste of time either. There’s some fun to be had, particularly in the early half of the film, both from entirely standard culture clash jokes-- rims on the golf cart!-- and some surprising, inspired nonsense. The groan-inducing pun in the title isn’t all there is to this ultimately well-meaning comedy.
Our hero here is C-Note, a.k.a. Christopher Hawkins (Outkast’s Big Boi, a.k..a Antwan Patton), a rap mogul who comes with his posse and two Range Rovers to the snooty Carolina Pines Golf & Polo Club seeking membership. The club’s president, Cummings (Jeffrey Jones, best known as the principal from Ferris Bueller’s Day Off), is horrified by the idea, and denies Hawkins membership on the spot. Hawkins responds in kind by buying property adjacent to the golf course and effectively bullying his way in.
Cummings hires a comely black lawyer (Tamala Jones) to try to settle with Hawkins, who spends the film seducing her and bringing her to the side of the good guys. In the meantime, Hawkins’ crew of oddball characters get into various sorts of trouble, from Big Large’s (Faizon Love) naked foray in the clubhouse bathroom to Lady G’s (Sherri Shepherd) reunion with her paroled husband on a dance floor. A handful of white people get to join the fun, notably Cummings’ son Wilson (Andy Milonakis) and a talented caddy (Cam Gigandet) with big dreams.
The acting in the film is by far the best part, with Patton making a charismatic leading man, and the supporting characters earning all the laughs (Love and Shepard both shine). Jeffrey Jones is game to essentially reprise his Bueller role, and blusters through the film appropriately. There’s plenty of terrible acting going on too- Gigandet is a huge blank spot, and Milonakis is just about intolerable-- but everyone mostly seems to be having a good time, and it shows.
The trouble in Caddy, oddly enough, comes from the movie’s attempts at actual emotion, including Hawkins’ romance with lawyer Shannon and a back story about Hawkins’ father-- a caddy at the club-- and his tarnished legacy that his son seeks to restore. Those who came for a good-time comedy full of booty-shakin’ and pot-smoking will be bored, while those who came to see an actual story are clearly in the wrong theater. The film hints at moments of anarchic weirdness-- a man called “Reverend J.J. Jackson” emerges out of nowhere at a key moment to deliver a rousing sermon, though no one has any idea who he is-- but eventually drags itself into a standard redemption story that’s no fun for anyone.
The lackadaiscal plot, cheesy jokes and lack of originality make Caddy nothing more than a trashy comedy, but at least it’s occasionally an entertaining one. Full disclosure: I saw this movie primarily because it was filmed in my hometown of Aiken, South Carolina, and expected to spend the whole time scanning the crowd for extras I recognized. The fact that my attention stayed with the action is testament in the film’s favor-- but it still didn’t make me any less anxious to leave when its 90 minutes were up.