Top 10 Movie Pimps

This New York City businessman maintains a streamlined business practice and he’s not afraid to flash a little pink. Although Willie Dynamite isn’t a herdsman in the biblical sense, he is a modern-day street organizer with an eye for fashion that would make Prince bow down in misery. He’s the #1 dreamer of the “pimp council,” but all the hardships that life brings threaten to destroy his aspirations of fluffy hats and a pocket full of cash. Willie may not be perfect, but his shaved head most certainly is.

“Wrong ain’t nothing but a word,” says this animated pimp, who rocks thick muttonchops and a striped purple jacket. After an impressionable nine-year old boy shows up at “The Playground” with a working girl, the Juice offers him a little “advice” along with a sprinkle of pimp glitter. Unfortunately, Fruit Juice becomes the victim of extortion, but his business acumen pays off once all the riff-raff cools down. This pimp walks to impress and he’s immaculately dressed. He’s the fruit juice your parents never told you about.

What happens when a journalist creates his own fictional pimp and the police question a real-life hustler? That’s the ultimate question in “Street Smart,” which features a 50-year old Morgan Freeman in his big screen breakthrough. With a relatively conservative thread game but an all-star Afro, Fast Black shows the way of the streets to Christopher Reeve’s character, the aforementioned magazine writer who writes up a story about a mystery pimp in order to save his job. Always large and in charge and a master manipulator, Fast Black gave Freeman an Academy Award nomination – and why not: it’s a smart and savage role that allows us to see his seedier side.

It’s the Capital S, oh yes, the fresh N double-o P, starring as Cordé Christopher, a peeyimp with a capital P. Okay, maybe only a handful of people actually watched “Boss’n Up,” since it went straight to DVD, but Snoop Dogg’s performance as a grocery clerk turned pimp is arguably a piece of art suitable for an American time capsule. It’s an existential story of business and love, with the fur-loving Cordé torn between the advice of Orange Juice and a woman named Chardonnay. You might say it’s the “Casablanca” of pimp films…said Cordé Christopher. Here’s lookin’ at you, bitch.

Is there anything that this pimp in white can’t do? After being framed Willie Greene and the 5-0, Dolemite serves his time before unleashing a proper whooping on those who messed up his pimp game. His boasts an upfront manner of speech, his agility allows him to hide in coffins and his karate techniques are simply poetry in motion. With a stable of women equally efficient in martial arts, Dolemite kicks ass and takes names, while simultaneously dropping rhymes about how he is kicking ass and taking names…quite the multi-tasker.

This Memphis pimp finds comfort in your basic white tank top and has dreams of becoming a lyrical gangsta of the music industry. You know what they say – it’s hard out here for a pimp and the proactive DJay finds unique ways to prepare himself for success…even if it means telling a few lies. In a surprising twist, one of his girls turns out to be a marketing wiz, which puts the sweaty hustler in a prime position to become the King of his own Graceland. Terrence Howard earned an Oscar nomination for his performance and Three Six Mafia won for Best Original Song. Hustle AND flow.

You’d think he was the office nerd if it wasn’t for his shiny gold chain and passive-aggressive manner of speech. After rich kid Joel Goodson gets all wild and crazy with a couple ladies of the night, he finds that Guido isn’t too thrilled with his risky business. So, what happens? Mom’s furniture disappears and the Windy City pimp applies more pressure while simultaneously preparing lunch. When it comes to name-calling, Guido destroys young Joel and gives him a life lesson that he’ll never forget.

Numerous hip-hop artists have referenced this Bay Area pimp and his suave style turned “The Mack” into a cult classic. After almost losing his mind up in the clink, Goldie hits the streets and learns the rules of the pimping game from an elder gent known as “The Blind Man.”: It’s not long until the “Mack of the Year” becomes infatuated with his own appearance along with controlling the minds of his potent lineup of women. Whether it’s Pretty Tony or Fatman or someone else with a strange name, nobody’s got the East Bay Funk like Goldie.

Love can make you do crazy things, especially when an Elvis Presley apparition offers a suggestion. As the target of a man smitten with a hooker named Alabama, Drexl Spivey talks exactly like his appearance: crazy. He pre-dated Johnny Depp’s Captain Jack Sparrow by several years and literally only has only a single normal eye for fashion. His accent sounds like he watched “The Mack” a couple too many times. But we don’t even care that he’s an overblown caricature, with his crazy clothes, drug habit and mean streak: Drexl is one pimp with balls. Or not.

Before we unveil our top pick, here are a few honorable mentions.
- T.J. Hicks
“Deuce Bigalow: European Gigolo” (2005)
- Flyguy
“I’m Gonna Git You Sucka” (1988)
- Ramrod
“Vice Squad” (1982)
- Chuck Lumley & Bill Blazejowski
“Night Shift” (1982)

Tight white tank top? Check. Fedora plopped on the head? Check. Nervous joking? Uh…checccck. Before Travis Bickle completely loses his grip on reality in “Taxi Driver,” he comes across a wise-ass pimp by the name of Sport. Although Mr. Higgins has a minor role in “Taxi Driver,” his scenes are filled with nifty one-liners and a vibrant charisma that make him and the cabbie an unstoppable comedy duo. Unfortunately, Sport loves pimpin’ and the socially awkward Travis simply ain’t hip enough to compete. Sport is the jolly pimp from the block that prefers laughter over violence. You know what they say, right? “Everybody’s gotta have a dream.”

Do you agree with our list? Who is your favorite movie pimp? For more mind-blowing Top 10s published daily, be sure to subscribe to WatchMojo.com.