There have been quite a few popes that have faffed to the masses about how sinful they are--hundreds, in fact. You can imagine how many fell short of saintly grace themselves. This podcast is us snubbing our noses at decrepit old fucks in robes who think they're better than us, or, worse, lay claim over our lives to "save" us.
This is not to say that all popes were bad; many did in fact render unto the poor. Pope Franky, while not exactly the picture of progressive enlightenment, is said to have dedicated himself to the poor to a somewhat noteworthy degree. But there's no question that throughout history, the Holy See has attracted quite the handful of ruthless, powerhungry pricks with a taste for domination, as well as people who just weren't altogether there.
It's important to note that many of these popes are only known to us by the writings of their enemies; as such, take these stories with a veritable pillar of salt.
This guy was held in contempt for centuries as your prototypical evil pope, poisoning the opposition and orchestrating wars at his leisure as a member of the conspiratorial Borgia family. He was also said to be really obese in addition to being a decrepit old fuck, which is gross enough already, but that didn't stop him from lining himself up some poon. Not even a miracle would have rendered this guy a good lay. Of course, if you look at this debauchery through a positive lens, you could say he was merely giving all those ladies the opportunity to engage in a tremendously charitable act.
The infamous Banquet of Chestnuts was his doing. Legend has it that not only did Alexander have less than reputable chicas bend over to pick up the chestnuts in the nude, he also had trained observers hang around to tally the number of ejaculations. White and red are the colors of the Vatican after all.
Furthermore, he was said to have been such a bloated creature that they couldn't even stuff him inside a reasonably sized coffin. Of course, that only makes me want to prove I'm better than him by eating even more and engaging in even more ostentatious hedonism. Couldn't the Banquet of Chestnuts have been improved by the measly addition of a cum birdbath?
It would behoove us to stress that he probably wasn't actually anywhere near that evil. His reputation is mostly drawn from his enemies, the Italian prelates and barons whose power he subverted. Two of Alexander's successors, Sixtus V and Urban VIII, described him as one of the most outstanding popes since St. Peter. But it's more fun to talk about a hypothetical monstrous hedonist. And, at the very least, it's very certain he enjoyed the company of many a mistress (but then, he wasn't exactly unique in this).
Becoming pope during a period of feudal violence and disorder in central Italy, when the Papacy was a pawn of warring aristocratic factions, this is the guy who cracked open the tomb of a former pope to dress his rotting skeleton up in formal vestments and try him in a kangaroo court known as the Cadaver Synod for his own satisfaction. The Cadaver Synod, without a doubt, really did happen. He even had some poor deacon answer "Because I was evil" beside the corpse in response to his honest demands for the truth, much like the Republican leadership's idea of a proper Beghazi hearing today. It must suck to have to act beside the stench of death, if he flubbed a line he'd probably be subjected to an even worse trial. He needed a better agent. Stephen followed through to the end and chopped off the three fingers that dead pope had used to bless people, and reinterred him in layman's clothes and then re-exhumed it, followed by tossing his corpse into a river, presumably via holy dropkick. This was just politics disguised as justice, and all the pronouncements of this trial have been annulled by the church. Stephen was also strangled later that very year by our next crazy pope.
He was kicked off the seat of Rome, only to to have it handed back to him, after which he lazily fell right back into the swing of things by launching a killng spree of supreme butthurt. If having two of his predecessor popes strangled to death in prison wasn't crazy enough, he also gave Stephen a laudatory epitaph. Politics, man. Oh, and he reportedly dug up the corpse of the same pope Stephen had a ball denouncing and tried him in court again. Following the wake of the Cadaver Synod, they put a ban on any sort of posthumous trials, and monk scooped his corpse back out of the river so he could be reinterred in St. Peter's Basilica--little did that monk realize he could have saved the backache as Sergius would just do it all over again, with a beheading of the body to boot. This second Cadaver Synod isn't well attested in history, so it probably isn't true, but hey, they do say history repeats itself. Anyway, Sergius also holds the distinction of being the only pope to sire an illegitimate child who would also go on to be a vicar of Christ. For more on this, listen to our Second Law episode on the "Pornocracy." I'm sure the jokes we made back then were entirely different so it's all right.