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During the period between the fall of Rome and the declaration of Papal infallibility the Roman Catholic Church was sometimes hard to distinguish from another traditionally Italian institution, the Mafia. At that time, all sorts of shrewd and sneaky schmucks infiltrated monasteries and seminaries, playing politics and pursuing power, and more often the key to eternal life and salvation was not prayer and good works but paying your weekly protection fee.
This eventually resulted in a whole lot of Popes that the Church isn't really proud of nowadays. Nevertheless, these gangsta popes deserve to be recognized for their cleverness and occasional supervillain-style.
10. JOHN XXII (1316-1334)
Compared to most popes on this list, John the 22nd was sort of a low-key guy-no big crazy orgies, no chasing sexy boys around, and relatively few instances of calling in a hit on his political or ecumenical (church-political) enemies. He's on his list for three main reasons: one, he was one of the Avignon Popes, who were all French dudes working for the French king and trying to make everything a little bit more French, which everyone else in Europe was really not down with at all; two, he was a huge opponent of the Franciscan monks and their belief that service to the Church implied a life of poverty and self-restraint (as opposed to his belief that service to the Church implied a life of drinking wine and making mad bank); three, he was sort of an awesomely sneaky and untrustworthy dude.
John XXII's most important and funniest trick was the one he played on the Roman cardinals in order to have himself made Pope in the first place. John's predecessor Clement V was the first of the Avignon Popes, but had died under mysterious circumstances before he was able to gain sufficient control over Church bureaucracy. The Roman cardinals found John's theology acceptable, and they were fairly grateful that he was probably the one who killed Clement, but they wanted assurance that this Avignon crap would stop and that Rome would remain the capital of the Church. John personally swore that until the papacy was returned to its rightful place in Rome, he would never allow himself to go from place to place on horseback ever again-and since he was 72 that basically meant he could never move more than ten miles in any direction without keeling over and dying. The Roman cardinals elected him Pope and he promptly walked down to the port and traveled to Avignon by boat, where he was perfectly happy to stay. Sucks to be you, Rome! -
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9. BENEDICT IX (1032-1036, 1037-1045, 1046-1048)
A refreshing change from all the creaky old popes who spent all their time debating theology and who died in office, Benedict IX mostly occupied himself with getting laid and got himself chased out of Rome no less than three times, the third time at the tip of a bunch of Imperial German spears. The nephew of Benedict VIII and John XIX, Benedict IX was basically forced into the family business by his dad when he was 18 or 20.
Considered the first primarily gay Pope, he was first kicked out of Rome for throwing gay orgies in the Lateran Palace, but managed to sneak back the following year. In 1045, he voluntarily sold the office of the Pope to his godfather in order to marry his (female) cousin for some reason, but he must've really missed those dude-orgies because he was back again the next year and fighting with his godfather as well as the other guys who occasionally stepped in to run things as Pope. After a couple years of this Pope-of-the-month silliness, the Holy Roman Emperor (actually a secular German king at the time) stepped in, shooed away all the Popes and rentboys, hopefully hosed out the Lateran Palace, and installed a completely boring reform-minded German bishop as Leo IX. -
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8. BONIFACE VIII (1294-1303)
Boniface VIII was elected Pope after his predecessor, Celestine V, more or less chickened out of the papacy and voluntarily stepped down. Boniface is best remembered for totally turning Popery up to 11 with his 1302 Unam Sanctam, which declared that it was "absolutely necessary for salvation that every human creature be subject to the Roman pontiff" and managed to piss off nearly everybody in Europe, including the king of France, the Holy Roman Emperor, and Dante Aligheri, who was the snarky political blogger of his time-this portrait shows Boniface after reading Dante's most recent ice-cold burn.
Unfortunately, the problem with using the office of the Pope to tell the most powerful crowned heads of Europe "Come at me, bro!" is that then those bros will absolutely come at you, and they'll be bringing an army with them. After excommunicating King Phillip IV of France and his chief minister Guillaume de Nogaret for the crime of frontin', Boniface took some time off at his Italian retreat in Anagni to chill, where was surprised to discover a small army led by one of the dudes he had just excommunicated. After refusing to step down and de-excommunicate the King and his minister, Boniface VIII had the crap kicked out of him, died of his injuries, and had a really mean poem written about him by Dante. Ouch! -
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7. JOHN XII (936-964)
John XII is a little tricky in that nearly everything we know about his run as Pope was written by guys who hated them and had a big chip on his shoulder. We do know for certain that he was made Pope at the age of 18 after a career of exactly zero years in the Church. How did he manage this cherry position?
Well, John didn't actually manage anything; his dad, the patrician (mayor/governor/big dawg) of Rome made church officials swear to make his loser son Pope upon the patrician's death.
Other historical records show that his heart wasn't really into the whole Pope thing, as enemy armies claimed a lot of papal land that he wasn't willing or able to try and grab back.
As a solution, he cut a deal with King Otto I of the Germans, which re-started the Holy Roman Empire that would spend much of its existence tangling with and occasionally declaring war on the Church.
In fact, Otto found good reason to pick a fight with his supposed ally pretty quickly, after John tried to renege on their deal by trying to get the Eastern Orthodox church back on his side.
But that's just the stuff we know for sure. The allegations of John's enemies were a lot more fun, including that he toasted the Devil with wine, ran a whorehouse inside the Lateran Palace, banged everybody's wife, had a dude's dick chopped off after an argument, and apparently set a bunch of fires just because he thought it was cool.I think we've all had a friend sort of like John XII, and while he was sort of small-time compared to other gangsta popes, certain traditions he started (especially an official Pope-sponsored brothel-man are we going to see a lot of those) came to define what it meant to be Big Popin'. -
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6. PAUL III (1534-1549)
Although far from the least deserving or qualified guy who was made pope, Paul III was notable for getting the papal nod almost entirely because his sister was having sex with one of the earlier popes, Alexander VI (who we'll definitely talk more about later).
Occasionally referred to as "Pope Brother-In-Law," Paul mostly just chilled out, bought art, and got jobs for his kids, often as cardinals. He accomplished a few significant things mostly by accident, such as founding the Jesuits, and he wrote one of the first papal condemnations of slavery with his Sublimus Dei (not that anyone currently making money off of slavery was willing to listen) shortly before turning around and repealing an anti-slavery provision in Rome in order to cut down on the city's homeless population.
Ironically, in spite of having kids all over town and having acquired his job principally by having a Pope-banging sister, Paul III is chiefly remembered for finally excommunicating Henry VIII the whole "murdering or divorcing six different women" thing.
Hank retaliated by forming the Anglican Church, which was essentially the Chinese counterfeit ePad to Catholicism's iPad, with the crucial difference being that the King of England could have sex with whoever the hell he wanted. -
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5. SIXTUS IV (1471-1484)
No, his name doesn't mean Six the Fourth-Sixtus is an old Greco-Latin name meaning "polished," and he was the first pope to choose the name Sixtus since the 5th century. Why?
Because the dude was totally polished, investing in a number of great art projects in and around Rome, such as a little place you may have heard of called the Sistine Chapel. To pay for this and other fun stuff, he eschewed the usual gangsta pope technique of running whorehouses and shaking down kings and instead declared a new fundraising effort to renew the Crusades against the Turks.
This round of fundraising was remarkably successful in every way except for how the Crusade itself never actually got launched, but hey, check out this awesome painting on the ceiling!
Even though Six-Four's art patronage played a big part in the introduction of the Renaissance, he's primarily known for his nepotism (which is sort of dumb, since half the popes on this list were Pope because they were somebody's son/cousin/nephew/guy they were having sex with) and for really, really wanting to kill Florentine big shot banker Lorenzo de'Medici.
Sixtus IV was generally considered to have messed around in local Italian politics more than was good for him, and his attempt to replace Florence's ruling family with one friendlier to him blew up in his face when de'Medici turned around and had all of Sixy's Florentine pet bishops executed. -
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4. SERGIUS III (904-911)
Another 10th-century Original Gangsta Pope, Sergius III won the office by having such good sex with his friend Theophylact's wife Theodora that she told her husband to go ahead and make him Pope, which must have been a pretty awkward conversation but has to be the most awesome way to become Pope.
Sergius' reign began the period that boring papal historians refer to as the "saeculum obscurum" (or "dark age") and what awesome papal historians refer to as the Pornocracy (or "rule of the harlots" which is a little less cool), in that it featured ineffectual Popes who usually did whatever their favorite mistress told them to do.
This meant that Theodora basically ran the Church for a few years until Sergius kicked her to the curb and took up with her daughter Marozia, who eventually gave birth to an illegitimate son who later on became Pope John XI. Handy!
Other than having hot sexy sex, Sergius' most notable achievement was digging up the corpse of Pope Formosus (a former political enemy) and chucking it in the river.
This wouldn't be too noteworthy if it was not actually the second time Pope F had been dug up by a dude who hated him, as previous totally crazy (but regrettably not very gangsta) Pope Stephen VI had not just exhumed Formosus' corpse but put it on trial, convicted it of perjury, and cut off its fingers. Man, were those dudes ever pissed at Formosus! -
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3. CLEMENT VI (1342-1352)
The fourth Avignon Pope (two popes after John XXII), Clement VI was by any measure a pretty decent dude. Taking office while the Black Plague swept Europe, he extended a "remission of sins" (sort of a Papal blanket pardon) to everybody who died of the Plague that hadn't had the chance to confess or receive last rites.
Upon hearing that Europe's Jews were being blamed for the Plague (because Jews got blamed for literally anything bad or even unexpected that happened in Europe, from sick cows to solar eclipses), Clement issued not one but two Papal bulls telling everyone to lay off the Jews and ordering all Catholic clergy to explain that those who blamed Jews for the plague had been "seduced by that liar, the Devil."
The "problem" with Clement VI was simply that the dude loved to party. While his predecessor Benedict XII was a clean-living earnest sort of guy, Clement almost immediately declared that "[his] predecessors did not know how to be Pope" and began painting over all the boring Crucifixion and martyrdom murals in the Avignon Vatican with more awesome fun scenes of hunting and fishing and dancing and such.
A lover of good music, Clement VI surrounded himself with composers and performers just in case he needed to throw an awesome Papal rager that required musical accompaniment. Many sources even report that Clement VI even bought up an old French palace to be used as a brothel that would both fund his parties and supply them with fine French hoes. When you get right down to it, Clement VI was basically just way too cool to be Pope. -
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2. LEO X (1513-1521)
Leo X is on the list because his stated philosophy was "Since God has given us the papacy, let us enjoy it."
Leo enjoyed the papacy so much that he managed to bankrupt it in two years, which he solved by pawning off some of the Church's priceless treasures, building a few more brothels and boosting the sale of indulgences, which were basically "get out of hell free" cards.
Leo loved the arts and sciences, donated heavily to charity, was an excellent musician, and was said to be so likable that he was elected Pope just because everyone thought he was a really cool guy-although being the scion of the super-wealthy and powerful de Medici clan probably greased the skids a bit too. Leo X was a high-rolling party animal, and by that time the rest of the Church was totally cool with that.
But some people were watching Leo rollin,' they were hatin,' and decided to catch him riding dirty in the eyes of the Lord. German theologian and legendarily un-fun guy, Martin Luther, was so angry about Leo's good-natured heresy that he posted his 95 Theses and ended up starting Protestantism, countless European wars, libraries worth of complicated religious arguments, and eventually, America.
When was the last time you partied so hard that your uptight neighbors formed a new country just to get away from you? -
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1. ALEXANDER VI (1492-1503)
If you lived in Europe at the turn of the 16th century, you would know Alexander VI as the guy who assassinated, enslaved, purchased you for use in one of his orgies, or (hopefully for your sake) bribed so that he could be elected Pope.
Yup, Alexander straight-up bought the Papacy, although he had a head start on the affair after his uncle Pope Calixtus III got him a sweet gig in the Church bureaucracy. He then commenced orgying it up old-school, having at least seven illegitimate kids, and murdering anyone who objected, anyone who disappointed him, or anyone who looked at him funny. No less than Giovanni de'Medici (the future Leo X) responded to his election with the words "Now we are in the power of a wolf, the most rapacious perhaps that this world has ever seen. And if we do not flee, he will inevitably devour us all." The joke was ultimately on Al, however-forensic evidence suggests that his death was the result of his similarly deadly and orgulous son Cesare accidentally poisoning his and his fathers' own dinner.