In the Iceberg Slim Episode of ‘The Dead Authors Podcast,’ Pimping Is Kind of Easy but Definitely Hilarious

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Of all the distinguished men of literature, no one, not even William F. Buckley, had as strong a pimp hand as the man the world would come to know, fear, admire, and emulate as Iceberg Slim. He was the most literary figure of the pimping world, as well as the most pimpish of influential and successful scribes. He’s also dead, which makes him the perfect subject for a posthumous chat with a time-traveling H.G Wells played by Paul F. Tompkins for yet another entertaining yet edifying episode of The Dead Authors Podcast.

And comedian and actor Ron Funches, with his warm and friendly voice (he sounds like a cartoon dragon from a 1980s cartoon) and preternatural likability, is an unlikely but inspired choice to step inside the persona of one of American literature’s grittiest icons. Funches makes this consummately unlikable man, who brutalized and exploited women, fueled his fury and violence with copious amounts of cocaine, and only turned to writing in his forties after a long street career that involved pimping something like 400 women (something that gets a smattering of applause during the live broadcast, before the applauders seem to realize what exactly they’re cheering) seem oddly likable and endearing in spite of himself.

Funches has a way of making even the most hateful and odious of statements sound charming. No one can say odious things like, “Heroin was a lot of fun for me” and “I thought you wanted to get into the ins and outs of beating women” (which Funches’ Slim says to Tompkins’ Wells after the time-traveling interviewer says that Slim, at his violent nadir, used to beat his prostitutes with wire hangers, an observation that leads, perhaps not surprisingly, to Wells cheekily referencing Mommy Dearest) and sound as bizarrely amicable as Funches.

The podcast begins with Funches as Slim reading a characteristically violent, grim, and lurid excerpt from Slim’s work that in this context becomes hilarious. The podcast benefits from a number of amusingly incongruous juxtapositions. First and foremost, there’s the juxtaposition of Slim’s strange dual careers as a man who terrorized and abused women for money, then launched a literary career out of his past misdeeds. Then there’s the even more incongruous contrast between Iceberg Slim’s cold-blooded menace and sinister calculation and Funches’ goofy, man-child sweetness. But there’s also the conflict between Iceberg Slim’s super-urban, bloody, and hyper-sexual realm and the relatively highbrow, cerebral, and literary world of H.G Wells and The Dead Authors’ Podcast. Funches as Slim tries to bridge that gap by suggesting Wells has a lot of pimp in him as well, and suggests his pimp moniker be “Ho Getting Wells.”

The podcast begins with Slim’s real work but quickly travels in the direction of gleeful absurdity, like when Funches as Slim says that his two great loves in life were pimping and water parks, and that water parks doubled as a “really good place to put your whores.” A series of crazy digressions follow from there, as Slim talks about how he realized that his pimping days were coming to an end when he unsuccessfully attempted to pimp squirrels and got a big, primitive early computer to help him with the elaborate scheduling and time-management that take up much of a pimp’s time, and found an unlikely secondary use for the computer, admitting, “When times got rough I’d put a skirt on (the computer) and see if people would fuck it for money.”

This leads to Funches as Slim and Tompkins as Wells role-playing a scenario where Slim tries to convince a john to eschew the usual and experiment with having sex with a giant, clumsy computer in a skimpy skirt by appealing to everyone’s secret erotic longing for Rosie, the robot maid from The Jetsons.

In The Dead Authors Podcast, the personalities of the dead authors being interviewed often blur and overlap with the comedians playing them. Sure enough, when the interviewee says things like, “If they take your smile from you, then they’ve won” and “I would consider myself an open flower when it comes to relationships” it sure sounds more like Funches than Slim. The episode’s odd positivity even makes solitary confinement seem less like a grim punishment than a nice little break when Slim posits it as a long-overdue opportunity for some “me time.”

Some of the podcast’s funniest and most memorable moments are simply taken from the real life of its subject, like when Tompkins as Wells mentions that Slim’s mentor killed himself after sixty years of pimping, but not before leaving perhaps the single greatest suicide note of all time: “Goodbye squares, kiss my pimping ass.” This leads to a glorious tangent where Wells and Slim discuss how this ancient pimp, who was born in the nineteenth century, lived an amazing life where he got to see so many new inventions being created that he could use to beat people with.

The Iceberg Slim episode of The Dead Authors’ Podcast is probably the single sunniest and funniest depiction of pimping in the podcasting world and possibly outside of it as well. Here pimping is actually pretty easy (as Funches as Slim concedes, the prostitutes really did all the hard work, and he just kind of coasted) and also consistently hilarious.

Nathan Rabin is the former head writer of The A.V. Club and the author of four books, including Weird Al: The Book (with “Weird Al” Yankovic) and, most recently, You Don’t Know Me But You Don’t Like Me.

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