It used to be that to become pope, you had to sit pantsless in a horseshoe-shaped chair and let a couple of cardinals see if you had the goods. If you passed, they'd yell "Testiculos habet et bene pendentes!" (He has testicles, and they hang well!) It's true, in those days it took balls to become pope.
Back then, the Papacy was reserved for the hardasses, guys you wouldn't mess with--the gangsters, the demon-summoners, the corpse-digger-uppers. Here are the ones we consider the biggest badasses. And, no, we didn't make any of this up.
#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."