Benedict IX

Now imagine this kid is the pope.

As horrific visions of Justin Cardinal Timberlake and St. Tupac tha Skandiluz flit through your head, just remember—it could be much worse. Consider, if you will, the case of Pope Benedict IX.

As spoiled a 12-year-old as ever there was, Benny ascended to the papacy in 1032. The office of pope was presented to him as a gift from his father, Alberic, the Holy Roman Emperor du jour. Benedict was the great-grandson of Marozia, a Roman Senatrix and powerful politician who was reputedly the mistress of Pope Sergius III. Through Marozia, Sergius was said to have sired Pope John IX. Several of Marozia's progeny ascended to the papacy, and Benedict's two immediate predecessors were also his uncles.

The stories about Benedict's behavior reached heights comparable to the most notorious popes. He was accused of habitual sodomy and bestiality, and was said to have sponsored orgies where any available orifice was considered fair game. His excesses were so legendary that they helped prompt St. Peter Damian, a cloistered monk, to write an extended treatise against sex in general, and homosexuality in particular, with a special focus on how these practices had become rampant within the Catholic priesthood and even the papacy itself. In Liber Gomorrhianus (The Book of Gomorrah), Damian railed against homosexuality in explicit detail for more than 100 pages, lumping in masturbation and dry-humping for good measure. Damian recorded that Benedict "feasted on immorality" and that he was "a demon from hell in the disguise of a priest."

Although Damian singled out Benedict for particular scorn, the diatribe was directed at the clergy in general. Benedict's sex life might have been colorful, but it wasn't exactly unusual. The papacy and the clergy at large had fallen into serious disrepute over the preceding 200 years. As a womanizer and a glutton, Benedict was merely indulging in the grand Roman Catholic tradition of the day, following in the footsteps of popes like Sergius and John XII, who transformed the Lateran palace into a brothel. Like Sergius, Benedict was also rumored to be a murderer with papicidal tendencies.

Despite the impressive efforts of his predecessors, Benedict did manage to distinguish himself as an innovator in the annals of bad popery. Not only did he repeat almost every sin committed by previous popes, he came up with one shocking new twist that no one before or since has managed to replicate—selling the papacy.

Benedict's grasp on the Church's supreme leadership was tenuous during the best of times. In 1037, he was ousted from the pontificate by an angry mob of Romans who were getting tired of all these sleazy popes. His political backing was strong enough to retake the papal throne within weeks without so much as a fight, though his enemies later tried to assassinate the pontiff while he was celebrating mass.

In 1045, Benedict was ousted by a more serious group of enemies, who replaced the hedonist with Pope Sylvester III. Benedict invaded Rome with force this time and regained his title within a matter of months. History likes winners, so Sylvester was retroactively declared an antipope. Contrary to his bloodthirsty reputation, Benedict allowed Sylvester to walk away and put him out to pasture in his old diocese.

After going to all this trouble, it took Benedict less than a year to decide he was bored with being pope. After he met a girl he wanted to marry, Benedict came up with a bright idea, one which would cement his place in the papal hall of shame: He would finance his new life by selling his pontificate to the highest bidder.

The buyer was Archpriest John Gratian, Benedict's godfather. Gratian was, by all accounts, a much better choice for pope than his godson. After the deal was sealed, Benedict stepped down and Gratian became Pope Gregory VI. This transaction didn't sit well with Sylvester III, who immediately sought to reinstate his own papacy. Gregory had bankrupted the church in the process of buying out Benedict, so he wasn't in much of a position to fight off a new claimant.

Matters only got worse when Benny's fiancee dumped him, leading the once and future pope to renege on the sale (he kept the money, however). Rome broke up into factions supporting each claimant. The clergy was more or less evenly divided between the three. Benedict easily cinched the support of the libertine faction, whose members suspected the day of reckoning might be at hand.

Finally, King Henry III of Germany was asked to step in and settle the matter. He invaded Rome in 1046 and called a council which threw out all three popes. Sylvester tried to fight for his claim and was sentenced to life imprisonment as a result. Gregory explained that he had meant well, admitted he was in way over his head and ultimately resigned. Benedict declined to show up for the proceedings, which was fine with everyone. He was condemned for his immoral ways and deposed from the papacy, allowing Henry to install a German bishop as Pope Clement II.

Benedict continued his efforts to reclaim the papacy by hook or by crook. Clement II died under mysterious circumstances after serving only 11 months in office. Benedict was suspected of poisoning the German. Either way, he took advantage of the opportunity and yet again installed himself on the papal throne.

It was a wasted effort. Henry had a firm grasp on Rome by this point, and Benedict had run out of friends and well-wishers. Because Internet was scarce in those days, it took almost half a year for Henry to find out that Clement was dead. Eight months later, Henry sent a new pope to Rome, along with an army to back him up. The new pope died of malaria 23 days later, and Henry sent yet another replacement, Leo IX, who had to put down yet another power grab by Benedict. Divinely inspired to avoid both poison and malaria, Leo finally put an end to Benedict's aspirations.

The former pope retired to a monastery near Rome, where he is said to have repented his evil ways and died shortly thereafter, according to Catholic church lore. Considering that Benedict would only have been about 35 years old at this point, this happy ending seems a wee bit convenient. But Leo IX went on to become a saint, so no questions were asked. Regardless of whether God, Leo or Henry did the deed, the sodomorrific papacy of Benedict had finally come to an end.