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Pimp My Pimp: Pimpiest Pimps in Pimpland

“When a hoe gets with a pimp, it ain’t no different than a Huxtable relationship.”
- Snooky Pimp

I don’t think truer words have ever been said.  I never could get through an episode of the Cosby Show without thoughts of prostitutes getting cold cocked by fleshmongers flowing through my brain.  “It’s Pimpageddon!” I would often cry out, as Cliff Huxtable massaged Claire’s tired lawyer feet.  Now, no one’s arguing that Bill Cosby didn’t play a fantastic pimp on television, especially during that whole “pimping out the darndest things kids say for cold hard cash” phase, but I’d like to submit my humble list of favourite celebrity pimps.  It’s rare that an article needs a soundtrack, but I highly recommend reading this one with Big Pimpin’ by Jay Z in the background.

Fly Guy

Arguably the last funny film to have the name Wayans attached to it, I’m Gonna Git You Sucka features one the greatest pimps to have graced the silver screen.  Not only was this playa skilled in the arts of hoe management, but when you peeled away the gold and the leopard print velvet, deep down he was an artist.  He demonstrated his sensitivity at the Pimp of the Year Awards, with poetry that could make the gods weep:

My Bitch Better Have My Money

My bitch better have my money,
Through rain, sleet or snow.
My hoe better have my money,
not half, not some, but all my cash.
Because if she don’t,
I’m a put my foot, dead in her ass.

Snoop Dogg

Since strutting onto the scene with his revolutionary debut album in 1993, Snoop Dog brought pimpin’ back with a vengeance. As the silky smooth rhymes and head-boppin’ beats of Doggystyle pumped forth from every car stereo system across the country, black and white teenagers alike could be seen cruising the streets, clouds of smoke billowing from the windows of their traveling hot boxes, all chanting those timeless pimp lyrics: G’s up hoe’s down while you motherf**ers bounce to this.

To see Snoop at his “pimpiest,” sitting as the head of the Pimp Legion of Doom, complete with pimp curls and pimp teeth, check him out at 1:30 in 50 Cent’s video for P.I.M.P.

Silky Johnson

One of the many legendary comedy skits to spew forth from the Chappelle Show, the Playa Hater’s Ball featured some of television’s finest pimps.   From the stylings of Ice-T as himself, along with Buc Nasty, Pit Bull, Beautiful and Mr. Roboto, you had more pimps than you could have shaken a pimp cane at.  But none could top the 2002 Player Hater of the Year, played by none other than Chappelle himself, Silky Johnson.

“The playa haters ball, gives an opportunity to hate on a diverse array of mark-ass marks, trick-ass marks, punk bitches and skip-skop skanks and scallywags. Hoes, heffers, hee-has and hooley-hoos.”

Pimp Puppets

Pimping knows no boundaries.  It cuts across sex, race, and even into the realm of the stuffed.  Pimp puppetry, or Pimpetry has proven that even with a human hand shoved elbow deep up your poop chute, you can still keep a scallywag in her place.

Statler and Waldorf

This pair of hecklers would certainly make the most hilarious pimps, if only for their relentless destruction of a hoe’s self-esteem.

Statler:  Hey Suzan, a Jon is offering top dollar to pee on our most beautiful skank.
Suzan:  Really?  So you think I’m the most beautiful?
Waldorf: No, but his brother will pay 50 bucks to have a poodle lick peanut butter off his balls.
Statler & Waldorf:  Ohhh ho ho ho ho ho!

I’m going to hell.

Elmo

Sick and tired of being tickled, Elmo becomes a self-proclaimed Pimpaholic.

The Counting Pimp

While Sesame Street taught little kids how to count, I would have never put two and two together about the Count had it not been for this bit from one of Dave Chappelle’s comedy specials:

Pimpin Snooky

From the documentary “Pimps Up, Hoe’s Down” comes Pimpy McPimperson himself.  From his naked lady gold ring statue, to his comparing a pimp/hoe relationship to that of the Huxtables, Pimpin Snooky knows how to “take the bitches to the concrete.”  A fun drinking game to play while watching this video is to take a sip of whiskey everytime Snooky says “know what I’m sayin’?”

On second thought, don’t play that drinking game, I nearly died from alcohol poisoning by 1:37.

And the winner goes to…

In 1975, comedian, actor, musician, and film producer Rudy Ray Moore gave to the world Dolemite. Based on his stand up comedy alter ego, Dolemite was a rhymin’, machine gunnin’,  kung fu kickin’, hoe bangin’ ass whoopin’ pimp.  Long before Samuel Jackson made his first movie appearance, Dolamite had already elevated the word “muthafucka” to new and exciting levels.  And as much as I can’t stand the overused writer’s cliché, Dolamite was truly and literaly, a warrior poet.  Now you’ll finally understand what the hell Snoop was talking about in Nuthin’ but a “G” Thang when he says:

Showin’ much flex when it’s time to wreck a mic
Pimpin’ hoes and clockin’ a grip like my name was Dolemite

Feel free to submit your contenders for the World’s Pimpiest Pimp.

Please note: This author does not condone violence towards women in any way shape or form…well, unless of course she’s a hoe who hasn’t paid her pimp all his money, in which case she deserves a pimp slap.