Alfonso IX of Leon, the Slobberer
Imagine you're reading an encyclopedia from the year 3008. You can easily find leaders like FDR and Lenin, but when it comes to politicians like Michael Dukakis or Howard Dean, you can only find entries for "Tank Man" and "That Guy Who Once Yelled on TV."
It's sort of like that for Alfonso IX. What were his accomplishments? Who cares! The guy drooled when he got agitated! Politics is a rough game: do one thing stupid in the Middle Ages, and humanity makes fun of you forever!
Vseslav of Polotsk, the Werewolf
In a purely historical context, this Belarusian king's biography is a snoozer--he's mostly notable for building a nice cathedral and fighting a bunch of other Slavic-sounding guys whose surnames throw spell check into conniptions.
However, he becomes an exponentially wackier guy when you look at his legends. When Vselav was born, a placental membrane was stuck to the newborn's head. Unfortunately for Vseslav, a nearby wizard advised Vseslav's mother to keep the dried baby cake stuck to his forehead for good luck, a piece of advice that is equal parts totally gross and super retarded. We couldn't make this shit up if we tried.
Wearing his own afterbirth as a wig every day didn't stop the ambitious young king. According to Russian folktales, the king developed the power to transform into a werewolf at the tender age of 28. Vselav's lycanthropic powers have been immortalized on Belarus' 20 ruble coin, thereby distinguishing Belarus as the first country in history to put a werewolf on their national currency.
Sadly, Vselav's kingdom never went to war with Transylvania.
Piero di Cosimo de'Medici, the Gouty
Piero's father Cosimo will forever be remembered as the founder of the powerful House of Medici. Piero's son Lorenzo will forever be remembered as a chief patron of the Italian Renaissance, a ruler whose court hosted such luminaries as Botticelli, da Vinci and Michelangelo.
Piero will forever be remembered for the uric acid build-up in his big toe.
Henry IV of Castile, the Impotent
Plenty of kings have had trouble producing an heir. Henry IV is unique for having his limp dick be the defining feature of his reign. This Spaniard's penile problems began when he refused to have sex with his wife ... for 13 years.
After a decade plus of no nookie, Henry decided that he wanted a divorce. Since his marriage was never consummated (a claim corroborated by lots of people peeping up the queen's skirt), and his gear supposedly worked (a claim corroborated by the local cathouses), Henry remarried and the new queen popped out a princess six years later.
Still, questions over his majesty's wood persisted. It's highly plausible that Henry bribed the prostitutes. A court physician further noted that Henry's physiology ("thin and weak at the base, but huge at the head") made it nigh impossible for the king to raise his scepter. To top it off, Henry's malfunctioning manhood likely caused his second wife to cheat on him, therefore nullifying his daughter's claim to the throne.
In sum, having erectile dysfunction is embarrassing enough. Having future historians hold colloquiums on your erectile dysfunction probably makes you glad you're dead.
Constantine V, the Dung-Named
This Byzantine emperor had his reputation swift-boated years before boats were ever invented.
If you think mud-slinging and political smear campaigns are harsh now, be thankful you never ran for office in the 700s. Constantine's unfortunate nickname comes from political opponents who accused him of shitting in a baptismal font as a child. The campaign was, by its nature, absurd; we all shit in weird places when we were babies as part of the natural pooping developmental process. But the fact that, 1,300 years later, Constantine's crappy nickname still sticks is both a testament to the remarkable persistence of the emperor's opponents as well as the colossal ineptitude of his PR team.
Frequent Cracked contributor Cyriaque Lamar's sci-fi political satire America 20XX will be performed at the 2008 New York International Fringe Festival from August 8 to 24 in lower Manhattan.
If you liked that, you'll probably enjoy our look at The 5 Most Ridiculous Lies You Were Taught in History Class. Or, enjoy a look back at a guy history's been a little kinder to, and find out why Once Jesus Got Famous He Changed, Man.