The 5 Biggest Badass Popes

5 Alexander VI (1492-1503)

Alexander VI blazed the trail for Biggie Smalls, Kingpin and Jabba the Hutt as obese badasses who didn't let their man-boobs and tendency to sweat while they ate stop them from amassing a huge fortune, slaughtering their enemies, and getting sweatily busy with the ladies.

Any story you've ever heard about crooked popes started with this guy. He bought the papacy with four mule loads of silver. He nailed Rome's most eligible bachelorettes. He made his 17-year-old bastard son an archbishop. He started wars, poisoned cardinals and took their money, and probably ate live frogs while feeding people to the Rancor.

His greatest accomplishment--as a host if not as a pope--was the Banquet of Chestnuts held in 1501. This sounds nice enough until you learn that the chestnuts were merely a pretext to have a pack of naked hookers crawling around the ground collecting them. But that wasn't the evening's only nut-related activity. Trained observers were present to keep track of the total number and quality of the party-goers' ejaculations. That's exactly the kind of information you need when a bishopric comes open.

Alexander's death was followed by further hijinks. His ham-stuffed corpse couldn't fit in the coffin and began belching sulfur. His successor forbade anyone from saying prayers for his lardy soul. Finally, almost 400 years later, he was reborn as Aleister Crowley (at least that's what he said), who shocked the world by ... taking a lot of drugs and drawing naked pictures of himself.

4 Pius II (1458-1464)

Pius II proves that appearances can be deceiving. At first glance, he'd seem to be in the running for biggest fancy lad in the history of the Papacy. He was a "humanist," which means that he read every bit of fruity Latin poetry he could get his hands on and then made ever-so-clever jokes about it with his similarly overeducated friends. Oh, how they giggled!

He seems like the kind of guy whose head you'd like to flush in a toilet, doesn't he? Well, it's a damn good thing you didn't try it, because Pius had a very powerful, very spooky man who was willing to do whatever the pope told him: fucking Dracula. Seriously.

You see, Pius had Turk problems. The Ottoman Empire was invading various European countries, taking Christian children from their families and subjecting them to strict training in order to create an army of super-soldiers (yes, really). Drastic action was called for.

Pius wrote a letter to Vlad III Tepes, aka Vlad the Impaler, aka Vlad fucking Dracula, a guy so bloodthirsty his name became synonymous with "vampire."

Hey, did we mention Vlad impaled about 30,000 people on huge-ass spikes? When Pope Pius took "drastic" action, he didn't fuck around.

In spite of the overwhelming odds--thousands of fanatical super-soldiers versus whatever mustached Wallachian turnip-farmers Vlad hadn't gotten around to impaling yet-- Vlad took on the Turks and even sort of won.

Whatever quality Pius had that caused Vlad the Impaler to put his own Transylvanian ass on the line to do his bidding, it makes him one of history's best-disguised badasses. The lesson: Resist the urge to assault the next tweedy little sissy you see reciting something in elegiac couplet, because it's quite possible that he has an undead bloodsucking fiend watching his back.

3 Honorius III (1216-1227)

Honorius III would seem to be one of hundreds of relatively uninteresting popes who fill in the years between the badass ones. But, like a furry with an erotic squirrel costume so convincing that against all odds it gives you an erection, Honorius was one of those guys who was so good at something lame that it actually made him a badass.

In this case, Honorius was so pious that the temptations of this world were too easy for him, so he routinely summoned demons just to challenge himself. He even wrote a book about it so that your local parish priest could test himself against the denizens of the netherworld by opening some kind of flaming portal to hell.

After a hard day of "reforming the clergy" (i.e., forcing them to be as unlike Alexander VI as possible), the meek and saintly old man retired to his chambers. His lackeys no doubt thought he was busily devising new ways to bore the hell out of them. Actually, he was drawing pentagrams on the floor and interrupting the slumber of various imps, cacodemons and even the final boss of his spiritual exercises, the terrifying spider mastermind.

What could be more frustrating for the demons? When one of these monstrosities is forcibly brought to the earthly realm, at least it usually gets to disembowel someone; depending on the skill of summoner, either the wizard's enemies or the wizard himself.

How do you think they felt when they came face to face with a bossy and spiritually invincible pope? "God be with you, my cacodemon. Now, do my dishes. After you're done, you can help yourself to a hard candy from the dish and then go back to hell."

2 Stephen VI (896-897)

Once he was ensconced on the throne (the nut-check apparently went smoothly), Pope Stephen VI decided to right some old wrongs. A previous Pope, Formosus, had committed some technical infractions, the kinds of minor crimes a less scrupulous Pope would have let slide, especially considering the man was dead. But not Stephen.

Consumed with an unquenchable thirst for justice, he had Formosus dug up, dressed in his papal vestments, and seated on a throne, ready to face the music in a formal trial.

It was like one of those Law & Order scenes where Jack McCoy starts yelling at a defendant, his eyebrows flying around like pissed off weightless caterpillars while the guilty bastard sits on the witness stand stunned into silence. Being as he was without an attorney and dead, all Formosus could do was sit there in his finery, perhaps letting a chunk of himself fall to the floor in silent protest.

Formosus was found guilty on all charges, of course, though the trial practically screamed for an appeal. The late pontiff's only defense was mounted by a cleric kneeling behind his throne, who answered Stephen's seemingly rhetorical questions ("Why did you usurp the papacy?!") for Formosus by explaining, "Because I was evil!" Historians do not relate whether the cleric set up a pulley device to make Formosus' jaw move up and down while he spoke for him, so we must assume that he did.

The death penalty was ruled out, since applying it to a corpse might have made Formosus a brain-eating zombie. Stephen played it safe: he chopped off the three fingers Formosus used for blessing and tossed his cadaver in the river. The lesson was inescapable. If the Pope was going to come down this hard on a guy who had violated an obscure Vatican by-law and died a year before, you didn't even want to know what kind of crazy shit he'd do to someone who really fucked up.

It's a testament to our lax and dissolute times that Stephen is now considered the bad guy in this story.

1 Sergius III (897, 904-911)

Take Stephen VI and put about ten extra inches of penis on him, and you get Sergius III. The only man badass enough to be forcibly removed from the office and to take it back, his seven-year reign left the landscape littered with corpses and papal bastards.

Stephen was first elected in 897, but Rome clearly wasn't ready. Perhaps the nut-check chair's hole was too small. Whatever the reason, he was expelled by force and excommunicated by various factions of player-hater. While Sergius sat at home and stewed, the papacy was fought over by some guys who were actually pretty badass in their own right.

Realizing that what was needed was stability through the accumulation of dead bodies, the gangstas running things in Rome invited Sergius back to his rightful throne. The new and former pope embarked on a program of governance that combined the best aspects of the first 100 days Franklin Roosevelt's presidency and the end of The Godfather. Sergius:

A warning to aspiring young mediums: do not invite Sergius III to a seance. There is no doubt that his spirit will snap your neck like a stalk of celery and then proceed to make time with your lady. Just don't do it.