— Shamelessly ripping off Caddyshack
— Degrading OutKast's progressive legacy by putting Big Boi at the center of a raunchy broad comedy filled with antiquated stereotypes and gratuitous farting
— Making whiplash-inducing tonal shifts between scatological crudeness and earnest drama involving Big Boi's attempts to avenge his father's humiliation at the hands of the racist country club where he worked
— Prominently billing Lil' Wayne for a blink-and-you'll-miss-it cameo without any dialogue
Defenders: Star Faizon Love, director/co-writer Don Michael Paul
Tone of commentary: Like the film it accompanies, the commentary track for Who's Your Caddy? is largely a broad culture-clash comedy, with Paul in the role of the clueless white guy who doesn't understand the mysterious ways of the Negro, and Love as the crazy, sass-talking black guy. Love spends much of the commentary explaining African-American culture to his hapless director. If Paul were to run for Whitest Man In America, he could use this commentary as his platform. Here are some choice excerpts:
[The scene: Finesse Mitchell sabotages the opposing team's horses before a big polo match.]
Paul: We also got some heat for this, that it was stereotypical that he was feeding the horse weed. That's probably true. What do you think, Faizon?
Love: I think you need to get out of the whole film business if you think this is… What do you mean "stereotypical"?
Paul: We've got a dreadlocked guy feeding the horse a bag of weed.
Paul: So he's back to Prince? When did he go back to Prince?
Love: [With uncharacteristic gravity.] About five years ago, Don.
Paul: What's a Proper? Trying to be educated and smart?
Paul: Help me out with this "Hell to the naw." Is that something she really says? It basically means "Hell no"?
Love: 4:20 is the code for weed. Did you know that?
Paul: No. Why? Are you being serious?
Love: 4:20. It's weed.
Paul: For all the people who thought it was racist to show a black woman frying chicken, I'm sorry.
Love: For all the people who thought this was racist, you should say "Suck my dick, suck my dick!" [Giggles uproariously for way too long.]
Paul: [About a song that plays late in the film.] This is what they call "backpacking rap."
What went wrong: The filmmakers didn't have enough time or money to shoot some crucial scenes fleshing out the story. Shooting was shut down at one point due to SAG problems. Actors (including Love) weren't getting paid and threatened to leave. The studio callously pressured a reluctant Paul (who characteristically grills Love on the enduring appeal of fart humor) into shooting a scene based around Love's explosive golf-course flatulence. A slew of scenes and characters were added with eight days of shooting left. Paul jokes that Love, whom he lovingly calls his "problem child" due to his lateness and irritability, clearly didn't read the script, since so much of his dialogue was improvised. He also refused to do more than three takes of any scene, or fly in a helicopter.
Comments on the cast: Paul and Love heap praise on pretty much every cast member, but remain curiously silent about their heavy, Jeffrey Jones. Late in the commentary, Paul awkwardly admits, "Jeffrey Jones had a tough time doing this movie. You guys made it a little tough on him… you guys are tough." Love earns special praise for refusing to wear a sock over his genitals in a scene where he freaks out an uptight white guy by prancing around naked. Paul was reluctant to let Andy Milonakis use what he squeamishly calls "the ninja word" until a visiting Eddie Murphy (who was dating producer Tracey Edmonds at the time) convinced him that it was okay. That's right: Paul used the man behind Norbit to gauge what was and wasn't offensive in a raunchy black comedy.
Inevitable dash of pretension: Love on shooting low-budget style: "That's the brilliance, to me, in this kind of filmmaking. Anybody can fucking take $150 million to duplicate something, but to take less money and create this right here is true art." This marks the first time the words "brilliance" and "art" have ever been used in connection with Who's Your Caddy?
The commentary in a nutshell: "After this scene, Faizon had to give me a whole education on ghost-riding the whip."