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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-like style.

    10. John XXII (1316–1334)

    Compared to most popes on this list, John XXII 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 this list for three main reasons. First, because 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. Second, 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). Third, 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 years old, that basically meant he could never move more than 10 miles in any direction without keeling over and dying. The Roman cardinals elected him, 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 fewer than three times, the third time at the tip of a bunch of 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 gay 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 popes. 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, 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.

    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 they will absolutely come at you, and they’ll be bringing an armies with them. After excommunicating King Phillip IV of France and his chief minister Guillaume de Nogaret, Boniface took some time off at his Italian retreat in Anagni, where he 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.

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    7. John XII (936–964)

    Understanding John XII is tricky because everything we know about his time as pope was written by guys who hated him and had big chips on their shoulders. We do know for certain that he was made pope at 18 after a career of exactly zero years in the church. His dad, the patrician (mayor/governor) of Rome made church officials swear to make his loser son pope upon the patrician’s death.
    Historical records show that his heart wasn’t really into the whole pope thing, and enemy armies claimed a lot of papal land that John wasn’t willing or able to retake. 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 reneged 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 Satan 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.
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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.

    Occasionally referred to as “Pope Brother-in-Law,” Paul mostly just 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 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.

    Despite all that, Paul III is chiefly remembered for finally excommunicating King Henry VIII of England over the whole “murdering or divorcing six different women” thing. Hank retaliated by forming the Anglican Church, whose crucial difference from Catholicism was that the King of England could have sex with whoever the hell he wanted.
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    5. Sixtus IV (1471–1484)

    Sixtus is an old Greco-Latin name meaning “polished,” and this pop was the first to choose the name since the fifth century. The dude was totally polished, investing in a number of great art projects in and around Rome, including the Sistine Chapel. To pay for this and other fun stuff, he eschewed the usual technique of running whorehouses and shaking down kings, instead declaring 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 Sixtus' art patronage played a big part in the introduction of the Renaissance, he’s primarily known for his nepotism and for really, really wanting to kill big-shot Florentine 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 had all of Sixtus' pet Florentine bishops executed. 
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    4. Sergius III (904–911)

    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 awkward, but is definitely the most awesome way to become pope.

    Sergius’ reign began the period that boring papal historians call the “saeculum obscurum” (or “dark age”) and what awesome papal historians call the Pornocracy, because it featured ineffectual popes who usually did whatever their favorite mistresses told them to do.

    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.
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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 plague swept Europe, he extended a “remission of sins” (sort of a blanket papal pardon) to everybody who died of the plague and 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), 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 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 whores.
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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 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 it.

    On the other hand, 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 and libraries worth of complicated religious arguments.
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    Next: A Gallery of Very Odd Church Signs

    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 you, enslaved you, purchased you for use in one of his orgies or (hopefully for your sake) bribed you 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, having at least seven illegitimate kids and murdering anyone who objected, disappointed him or looked at him funny.
    The joke ultimately was on Alexander, however. Forensic evidence suggests that his death was at the hand of his similarly deadly and orgulous son Cesare, who accidentally poisoned his and his father's own dinner.