Title: Who’s Your Caddy?
Genre: Comedy/Sport/Plagiarism
Cast: Big Boi, Faizon Love, Jeffrey Jones …
Director: Don Michael Paul
Release: (2007)
There is an unspoken secret among those of us who write as critics of pop culture. And since my lawyers have assured me that “writing” it is still technically not “speaking” it, I feel confident that I can let you in on it here without breaking that unspoken trust in a way that would be grounds for my disbarment. The secret is this: we are predators. Like the savage lions of the Serengeti, we hunt for our prey and feed on the weak. We use our best reasoning to size up our prey, and certainly there are plenty of strong works out there that command our respect and inhibit any attacks. But every now and then, out of nowhere, a lost and injured gazelle will just come hobbling right into our lair at dinnertime. Our eyes get wide, we lick our chops, look around at each other for a second, and then just pounce and feast relentlessly.
So when ads for Who’s Your Caddy? started hobbling over the hillside and into our sights, critics everywhere started salivating and prewriting the pithy remarks with which to slaughter their prey. (Any critic who tells you they didn’t spend several days debating whether their editors would let them call it “Caddyblack” is a shorts-soiling liar.) It’s not so much that the commercials looked terrible, though they did. It’s not even so much that someone would try to do an updated remake of the revered classic that is Caddyshack to appeal to what snivelingly milquetoast marketing executives euphemistically refer to as a more “urban” demographic, though they did. But the fact that they would do so with the unmitigated gall to try to pass it off as an original work, without so much as an implicit acknowledgment that this movie literally was Caddyshack, now THAT was the rub. And so we went with our crude hunting tools – the sharpened pencils, the dog-eared moleskin notebook that we want girls to see us writing in, the stupid Matt Drudge hat – to slaughter the beast and consume its entrails with melted butter and extra salt. But a funny thing happened to me when I gnawed off my first hunk of furry skin. I laughed (and a little blood came out my nose).
I didn’t laugh alot – but still. I mean it was only like four or five quick times (and three of them were literally at the same exact joke, used the exact same way at three different times in the movie), but they were out loud. I was mortified! How could I face my smarmy, self-important peers? How could I face my smarmy, self-important self? I felt like George in that Seinfeld episode where he gets a massage from a male masseuse and then spends the rest of the day racked with embarrassment and self-doubt because he “thinks it might have moved.” (Not that there’s anything wrong with that.) What about all my pithy remarks? They had all that pith! What about all my searing commentary? It seared so freaking much! I can’t kind of like this movie, I’m me!
And so it is that I find myself at this proverbial fork in the road (I don’t exactly remember which Proverb this same situation was found in but I think it was, uh, ten). In the past when I have been faced with other such difficult decisions in my life, I have found that it helps to find a quiet place, turn off all the distractions of the outer world (except the TV and the strobe light), relax in the lotus position, and write brief plot synopses until the path of truth reveals itself to me. Excuse me now while I open my mind to receive this truth.
Who’s Your Caddy? is the truly, completely and unapologetically unoriginal story of a group of cool, young fun-lovers who stand up to the stodgy, old establishment and show them that rules were made to be broken, man. This time, the young, fun-lovers consist of millionaire rapper C-Note, played by proud pit bull farmer and Outkast rapper Big Boi, and his sassy posse of stereotypes. The old establishment is played mostly by the increasingly creepy Jeffrey Jones, in what will probably go down as his last appearance in anything outside of a Roman Polanski ‘Special Interest’ film. Despite this solid casting, I couldn’t help but notice that just about every major golf equipment company in North America remained conspicuously absent from a number of obvious product placement opportunities throughout the film. Hey Ping, dog-fighters and felony sex offenders golf too, you know. Think outside the box.

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