The only work-safe part of this picture
Like Caligula, Sade was a go-getter who viewed an ass as an ass regardless of whether it was male or female. During his time out of prison, he had problems retaining any staff as few maids and servants responded well to his buggering and gerbiling or whatever it was he was doing for kicks. When not on the run, he was known to arrange orgies around town, and apparently had a thing for mixing sex and blasphemy in unique and uncomfortable ways, such as inserting communion hosts where no communion hosts have gone before, or wanking with crucifixes.
Trust us, they're all naked
Even bloating with old age, Sade never really grew out of his debauchery, even when he found a woman willing to stay with him despite his reputation and nefarious hobbies. He died in prison, while having an affair with a teenager who worked there. We're thinking the man wasn't sorry.
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.