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.
If the stories are to be believed, when not busy murdering people for fun or money or having people tossed in arenas with wild animals to amuse himself and his horse, Caligula was known for turning his palace into a brothel, something that just wouldn't fly in today's Buckingham Palace due to the Queen's poor hips.
Penthouse founder Bob Guccione on the naked set of Caligula
He also had a tendency to pick up any random women who interested him. Women at their own weddings, for instance, or pregnant women. Or one of his three sisters. Or the wives of people he was having dinner with, which he would inspect like mom looking for the best melon at the supermarket before taking them away, doing his business, then coming back and giving everyone else the highlights.
And being that variety is the spice of life, he was open to men as well. The son of a consular family "had buggered the Emperor, and quite worn himself out in the process," as one historian writes.
See, we would have paid more attention in history class if they hadn't kept leaving out stuff like this.
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.
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.