Six Fascinating Videos of Real Life Pimps In Action

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Pimps. So many ladies, so little time. What can we learn from those men who dedicate their lives to working as middle men between the guys who must pay for sex and the women willing to sell it? A great deal, as it turns out. No matter how you pimp walk it, hustlers are an intriguing lot. Thankfully, YouTube is chock full of pimps showing off their bling, preaching pimpology, and demonstrating why green is for the money and gold is for the honeys.

Here, we present the six most fascinating pimp videos.

The Holy Pimp

True story: I spent an afternoon with Bishop Don Magic Juan, one of this country’s most famous pimps, also known as “spiritual advisor” to Snoop Dogg. He let me hold his pimp cup, showed me his see-through toilet seat lid with coins embedded in it, and nicknamed me Angel. The Bishop is a true fashion plate among pimps, regularly seen sporting green and gold suits paired with dollar-signs sunglasses. You wish you were so fly.

Pimp Gets Knocked Out

When Three 6 Mafia sang their Oscar-winning hit track “It’s Hard out Here for a Pimp,” they were not lying. Behold, this pimp finds himself in a spot of trouble as he wrestles with one of his ladies of the street corner. His hot pink hot pants-wearing employee tears his shirt off during the tussle. Breaking free, said pimp heads over to an onlooker, who distracts him with a right and clocks him into another dimension with a left. Getting black eyes is just part of pimp life.

Fillmore Slim, Still Pimping

“I wanted me a Cadillac.” So explains pimp godfather Fillmore Slim — real name: Clarence Sims — the “Pope of Pimping” who ruled the game in San Francisco and years later become a famous blues singer. In this video, Pope Slim reveals how he got his start hustling in Texas, shares that pimping is all about giving, and recollects the good ol’ days when pimps did little more than ho watching.

Iceberg Slim Is an Undercover Brother

In what is quite possibly the strangest and most compelling pimp interview on the Internet, the noted late pimp Iceberg Slim discusses the life of a hustler and how a con man named White Folks ran his con business. When I was in college, I read Iceberg’s Pimp: The Story of My Life. Today, I remember next to nothing about it other than I found it completely mesmerizing. Almost as mesmerizing as the crazy hood-and-goggles disguise Iceberg wears in this interview from 1968.

The “Citizen Kane” of Pimp Movies

If you haven’t seen the 1998 HBO documentary “Pimps Up, Ho’s Down,” you haven’t lived. Created by Brent Owens, who was also the man behind “Hookers at the Point,” the doc takes an unrivaled peek at the country’s most famous pimps and the players’ balls they attend. Starring the Bishop, former pimp Ice-T, and the most memorable white pimp in American history, it is a pimp movie not to be missed.

Dear Pimp

Suga Free is a pimp who was born in Oakland and raised in Compton, which is about as hardcore as you can get coming up in California. Free became famous as a rapper, but supposedly he always considered himself more of a pimp, which was his original career, than a rhymer. Perhaps you remember his 2008 album, Smell My Finger? Free has since taken to doling out advice to those in need of counsel. After all, who understands gender dynamics better than a man who made his living off of them? Suga Free is the 21st century’s Dear Abby.

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