7

Chuck Negron

The lead singer of Three Dog Night took sex where it was never meant to go. Being the lead singer of a band back in the '70s, it's no surprise Negron has probably experienced things the rest of us can barely comprehend, such as a $2,000-a-day drug addiction. He took it further, however. Much further. So far, in fact, that his penis exploded. No, we're not speaking figuratively.

While Gene Simmons can claim he's slept with a bajillion women, based on the recently released tape of his coitus, his medicated-bear approach to love making isn't going to strain him any time soon. Chuck Negron, on the other hand, presumably experiencing an entirely new plane of reality with the helping hand of massive amounts of cocaine, worked his crank with so many women and with such drug-fuelled ferocity that a doctor told him it had become the tumescent equivalent of a lucky pair of boxers. Sure you want to keep using it, but the edges are frayed and the material holding it together is mostly made up of your hopes and prayers more than any real atomic bonds. One more tumble through the wash and she's done for.

This horror is outlined in Negron's autobiography, the writing of which apparently means he retained his sanity after what has to be the most traumatic event possible in this universe.

6

Xaviera Hollander

Known as the Happy Hooker, Hollander is who Eliot Spitzer would have been paying $1,000 a night for if he'd been in the market back in the '60s. And given the state of inflation, that means today she'd be making over $6,000. That's some expensive whoring, but despite the high prices, Hollander stayed busy. Boy, did she.

A one-time secretary from Holland, she decided a desk job was for suckers and maybe banging strangers for cash would be a more lucrative trade. And since we all know Holland has no debauchery at all, she left for America.

Hollander was New York's top madam back in the late '60s and early '70s, and even wrote a book about her life selling her ass that was made into a movie. Eventually she acquired a job writing a column for Penthouse, worked as a phone sex operator and wrote several books that were mostly about fucking.

If there was a way to be filthy, she tried her hand and probably one or two other body parts at it.

5

Casanova

Giacomo Girolamo Casanova de Seingalt is one of the most iconic man whores of all time. Known as one of the world's greatest lovers, he met popes, royalty, Voltaire and Mozart, probably leaving all of them wishing he'd given them a taste of his sweet, sweet love.

According to his autobiography he started his sexual life with something of a bang, losing his virginity at 16 to a pair of sisters who threw themselves at him. We're assuming that was the age Casanova decided he simply could no longer deny the world the benefits of his sexual superpowers.

And he was not a good-looking dude

Throughout his life he hopped all across Europe, partly for sport and partly because he got kicked out of nearly every city he went because he screwed more women than modern pay scales. More than once, his final act before leaving town was fighting a duel with someone over a woman he'd introduced to his penis. As a businessman he made and lost literal fortunes, amounts that would be in the millions today, because he had to continually pay off women who worked for him after some random night of debauchery or, once again, as a result of having to leave town due to various shenanigans he and his boner were up to.

4

John Holmes

"Johnny Wadd" was the porn star to end all porn stars. Appearing in over 2,500 flicks and inspiring films like Boogie Nights, Holmes was the Ron Jeremy of his time, only not as fat, hairy and horrifying. So not really like Ron Jeremy at all.

Discovered by a man at the next urinal staring at his package, Holmes started earning $3,000 a day for his movies by the late '70s. His claim to fame was having the dick that all other men merely claim to have. He once described it in a scholarly fashion as being "the size of two and one half 6-inch rulers" though his wife said it was closer to 10 inches. A woman can sense these things.

Holmes claimed to have had sex with 20,000 women, though he was known to be something of a bonehead and a liar who would often make up a story one day and recount it as truth the next. People with more of a reputation for honesty (and less of a reputation for sucking back as much cocaine as Holmes did) say the number was probably closer to 3,000, which for most people is still pretty impressive. Or disgusting. Really depends on one's outlook.

3

Caligula

Let's start by noting that when it came time to make a movie about Gaius Julius Caesar Augustus Germanicus, known as Caligula, nobody called Ridley Scott or Stanley Kubrick. No, for this particular Roman emperor, the only type of movie that would suffice was a 3-hour-long porno funded by Penthouse magazine.

That's because Caligula is mostly known for one thing: stark, raving depravity. Though some stories were most likely exaggerated and the sources can never be fully verified, the legacy he has left behind involves a lot of whores, adultery, incest and a horse that used to get invited to dinner and that he tried to get appointed as consul.

2

Marquis de Sade

Donatien Alphonse François de Sade probably doesn't have a great reputation outside the whips and chain crowd, given that his major legacy is being the source of the word "sadism." If he was the Marquis de Fellatio or the Marquis de Philly Cheesesteak he might be more widely loved and respected, but oh well.

A French aristocrat and philosopher, Sade spent much of his life either incarcerated, both in prisons and nut houses, or doing things that would get him put in prisons and nut houses. A big fan of hookers, he was mostly known for engaging in nefarious and abusive acts that he probably had to pay extra for. What kind of acts? Things like poisoning them with Spanish Fly, or the scourge of polite society: sodomy. And, you know, the sadistic stuff that made him famous.

1

Wilt Chamberlain

Not just an awesome Conan villain, Chamberlain was a monster on the court and is the only player to have ever scored 100 points in an NBA game. He was also the man who, like John Holmes, claimed to have banged 20,000 women. Though it was probably not the same 20,000 women because that would be an astonishing coincidence.

According to some people who know math, for Chamberlain's claim to be true he would have had to have sex with 1.14 women every day from the time he was 15 until he died. Factoring in things like sleep, work and his inability to score quite as often in his younger and later years, has him doing the deed with a different woman every three and a half hours. For 21 straight years.

Wilt's penis snags a rebound

While that makes it seem like most people doubt him, those who knew him said he easily arranged for threesomes and was known to have more than 23 women over the course of one 10 day road trip. Toss in a lot of charm, being rich and famous and the fact that the story is a lot cooler if it's true, and we see no reason to doubt it.

Wilt modestly hides his escaped penis with the ball; an opposing player averts his eyes

Chamberlain faced a lot of criticism for his claim, but always stuck by it and never said he was bragging, just laying it out there because people were curious, which is probably how at least a few of his sexual encounters started as well. And while Wilt seemed to feel like he had to constantly explain why he slept with enough women to populate a small city, we're pretty sure "Because he could" just about covers it.

If you enjoyed that, check out our rundown of The 10 Nakedest Female Names on Google Image Search. Then, watch some(one else watch) PORNOGRAPHY ON CRACKED.COM!!!. Or if our dishonesty in that last link pissed you off, you can actually see barely blurred pornography in this hard hitting piece of political commentary.