Thomas Jefferson won at life. He could more or less turn his attention to anything and it would turn into gold. He was the third President of the United States, and wrote The Declaration of Independence (you might remember it from the time it was stolen under the cover of a poster sale in National Treasure).
As a politician, he used his throbbing brain to pimp slap the French and the British back from whence they came. In the White House he threw wild parties, habitually greeting guests in slippers and a dressing gown. Essentially, he became the Hugh Hefner of a Capitol Playboy Mansion. Also, Jefferson's support of the Second Amendment assured fellow-pimps the right to stay strapped for years to come.
When Jefferson left office he couldn't find a university that could handle his terrifying intellect, so he just started his own.
Pertaining to Poon:
Jefferson's wife was already a widow at 23 when they hooked up after her previous husband died in an "accident."
She went on to have six of Jefferson's children, which of course provided only a small fraction of the fucking T.J. required. That's where one of Jefferson's slaves, Sally Hemings came in. The affair between the two never even found an official denial despite heavy press coverage, though he never officially admitted to it, either. It is thought that Jefferson's deathbed confessional treatise, "I Like Big Butts; And I Cannot Lie" was burned by those close to him before it could be publicly released. Since then, inconclusive DNA testing has been done and has found links between the Jefferson and Hemings' offspring, though not with ol' Tom-boy himself.
To make things even juicier for Jeff, she was purportedly his wife's half-sister. Did we mention his wife was his distant cousin? Put it all together and you have a recipe which, when left to bake in the heat emitted by Jefferson's nut sack, rises to become an extremely kinky layer cake being eaten in the White House.
Ohhh ... shit. He's representing well before his time, here, decked out in a Superfly-style fur coat that makes Davy Crockett's hat look like a raccoon mullet. There's also something to be said about any man daring enough to wear a cravat. And, that look on his face is as ice cold as murder. But the real points he scores here aren't from his clothes, but the fact that he sported more bling on his head than any pimp ever recorded--chrome hair.
While this guy was always dropping dope lines, we felt the most pertinent to pimpology was this little gem, "Always take hold of things by the smooth handle." And by things, he means him, and by smooth handle, he means his penis.
2King Charles II
As a teen, Charles II fucked his way through half of 17th century France and Holland. He led an invasion of England from Scotland and was placed on the throne by popular demand and, once there, celebrated in style.
His reign included mountains of drunken debauchery piled one on top of the other as a previously sexless England celebrated his reign with a good ol' fashioned fuck-out.
Pertaining to Poon:
He and his wife, Catherine, had three marriages, no divorces. Not satisfied with one lavish ceremony that spanned nations, he decided to throw two more when she arrived in England, presumably because one honeymoon wasn't enough time to squeeze romantic things like eating and sleeping in between the sex. When he wasn't getting married, Charles' dick ran through seven buxom mistresses like a cruise missile, producing 12 bastard sons. And, that doesn't even include the countless whores.
As king, he was in charge of the whole country, including its whores, so any street pimps were technically deputies he put in place to watch the corner while he was off tending to business. John Wilmot, chum and fellow rampaging nymphomaniac said of him, "Restless he rolls from whore to whore, a merry monarch, scandalous and poor." This perception was shared by absolutely everyone at the time, and like pimps of today, split opinion over whether or not this was a good thing. Clearly, most of the country not in the Houses of Parliament thought it was. His reign turned every alleyway and dimly lit area into a writhing mass of peasants indiscriminately humping each other.
With so much Dalmatian fur and red velvet, he can't actually sit in his throne. He would cup a big golden ball in one hand and hold his solid gold pimping cane erect in the other, with his crotch pushed conspicuously forward, a crown twice the width of his head and a cushion for his feet that costs more than your house. Apparently, the artist decided not to include the bikini-clad girls draped all over him at the time of painting. Nevertheless, it's a struggle to think, even in such a ludicrous genre, of how this could be more pimping.
Or, it would be, if he hadn't had medallions made depicting himself as a Roman Emperor. Regular pimps quibble over money. This pimp put his face on it. Short of tattooing "PIMP" across his tongue, there's little this guy can do to best himself. Oh, what's that? A solid gold statue of himself as a Roman Emperor? Yeah, that'd be just about fucktastically insane enough to do it.
Charles was undoubtedly battle-rapping a Quaker with crotch in hand when he dropped this bomb, "For its merit I will knight it, and then it will be Sir-Loin." The Royal Court presumably turned into an 8 Mile fiasco of whistling and hooting--a trend since upheld in modern-day Prime Minister questions.
Also of note, in a heroic gesture of pimping benevolence, he successfully managed to predict the future backlash against pop-rap artists, commanding upon his death bed, Let not poor Nelly starve."
Pictured: Nelly, short on pussy by Charles II's standards.
There can only be one conclusion. Just as he was King of Britain, so was he King of Pimping, not treating it just as a way of life, but a way of everyone else's lives, too.