Catholic pope (1502-1542). He was born Gregory Boyardee, 12th and youngest child of an extremely wealthy family of girdle manufacturers in Genoa, Italy. Realizing he didn't have the stomach for all the fratricide necessary to inherit his parents' money, he decided to enter the priesthood and hope he could somehow luck his way into insane wealth as a Level 1 Cleric. 

This may sound foolish, but it wasn't a terrible idea. Being a Man of God has always been a great way to get rich. But it usually requires some time to work your way up the career ladder of the Church. And it also requires at least some intelligence. And Gregory was not smart. Gregory was dumb. He was basically Donald Trump, Jr. without the animal cunning. He had serious trouble learning classical Latin, so he always had an acolyte nearby who could tell him how to pronounce words during Mass. He couldn't remember the right order for Communion and sometimes used cheap rum when he ran out of wine. He remained convinced for months that the books of the Bible were named for their authors, so Ephesians was supposedly written by a guy named Ephesian, for example.

Nevertheless, Gregory had a very important advantage to fuel his rise in the Church -- his superiors in the church were convinced that if they promoted him, his family would give them money. They were wrong -- his family mostly didn't care what happened to him. But they were wealthy, so they were big donors anyway. So the Church, assuming they were giving money because of their nitwit son, just kept promoting him. 

So by 1535, Gregory was an actual cardinal. He was likely the most ignorant and embarrassing cardinal in a few centuries. He giggled uncontrollably any time he heard the name of the prophet Hosea's wife, Gomer. He never managed to properly pronounce Zebedee (the father of James and John) -- he kept repeating the last two syllables over and over. He told close friends he doubted the virgin birth because "how could God get His giant thingy in Mary's little thingy?"

At this time, the current fella overseeing the Holy See was Pope Orcus IX, widely considered the 11th most evil pope in history. (This was back when the forces of Hell were a lot more open about the Popes they were controlling and a lot less willing to engage in subterfuge.) Orcus had enjoyed a decade of running the Vatican like his personal chamber of horrors, and the rest of the cardinals were either trying to stay out of his torture vaults and orgy chambers, or trying to push their cohorts in, to get them out of the way. But eventually, Orcus pissed off the wrong Demon Prince and got devoured by his own goat orgy

This left a bunch of cardinals who wanted Orcus's job and mostly hated each other and generally refused to vote for any worthy candidates. So after two weeks of fighting, voting, weeping, and back-stabbing (mostly figurative), most of the cardinals were hopelessly disgusted with the entire process, and most of them started voting meaningless protest votes. Unfortunately for the Church, the third round of random protest balloting gave a full two-thirds majority to Cardinal Gregory Boyardee. 

So on the bright side, the Catholic Church no longer had an actively evil pope. On the semi-bright side, Gregory VIII was also unimaginative enough that he wasn't going to start any waves, cause any trouble, or push for any reforms.

But on the not-bright side, Gregory was dumb. He'd never been able to learn proper Latin, and now that he was pope, it was felt that it was undignified for him to rely on an acolyte to read him his lines during Mass. So instead, a high-ranking cardinal hid under the pulpit and read the Mass, which Gregory would then repeat for the faithful. This fooled absolutely no one. 

Gregory was also responsible for the construction of the wall surrounding Vatican City, having become convinced that swarthy Italians were sneaking across the border to steal jobs within the Holy See. It was, of course, pointed out that Gregory was himself an Italian, but he insisted he was one of the good ones, not like those dirty Romans. (This did not endear him to the various Church officials who were from Rome. It also didn't endear him to anyone from Rome, or in fact, to anyone from Italy.) Still, he was the pope, and the pope was rich. So he paid for a wall. And no one paid any attention to it, because Gregory was an idiot. 

However, the biggest controversy Gregory was responsible for happened in 1540, when he released his first Papal Bull. It took every cowboy in Rome to capture it afterwards. 

Gregory's final downfall came about because, well, he was dumb. He got the idea into his head that the Vatican's greatest work of art was painted on the ceiling of the Cistern Chapel, not the Sistine Chapel. Cardinals, bishops, and other clergy took him to the Sistine Chapel over and over and said, "Look, Your Holiness, up there, that's Michelangelo's greatest work up there," and he refused to believe him. They told him he was misunderstanding the name of the chapel, and he didn't believe them. They told him there wasn't any kind of chapel in any kind of cistern anywhere in the Vatican, and he refused to believe them. 

So they finally took him to the largest cistern within Vatican City to see for himself. It was a large cistern -- not as large as some of the big ones elsewhere in Europe and the Middle East, but large enough for more than one person to enter and stand upright in. Gregory walked in, and he laid down in the water so he could look up and see the painting he imagined was on the ceiling of his Cistern Chapel

And he drowned. 

Pope Gregory VIII was succeeded by Pope Justin IV, who was only a little bit better. 

For reQuest 2019
("I want Jet-Poop to write a node about Pope Gregory VIII without doing any research whatsoever.")