João de Sá Panasco, The Freed Slave Who Served As Court Jester For The King Of Portugal

Public DomainPanasco’s role as a jester offered him a unique opportunity to hurl insults without repercussions.
Black men in 16th-century Europe weren’t typically afforded much opportunity, but João de Sá Panasco beat the odds to become a member of King John III of Portugal’s royal court — even if it was only as a jester.
According to Modern Rogue, little record of Panasco’s private life exists other than the knowledge that he was enslaved at one point, but accounts of his time as a court jester have survived.
The position afforded him a certain freedom despite the fact that those in the court despised his “inferior condition.” His wit and ability to hurl verbal insults, however, made him a favorite of the king.
Panasco also benefited the king because of his roles as both “outsider and insider.” As the court’s jester, he could entertain guests and play the fool — and then act as the king’s informant after the fact.
King John III reportedly thought so highly of Panasco that he arranged a marriage for the jester and even named him a member of the Order of Santiago, otherwise known as the Military Order of Saint James of the Sword. It was an esteemed position for anyone — particularly a formerly enslaved Black man.
Of course, none of this shielded Panasco from racist remarks made by courtiers, and he eventually fell into a deep depression, turning to alcohol to cope. Still, his story is impressive, given that he worked his way from slavery to being a “gentleman of the royal household.”
Perkeo Of Heidelberg, The Jester Known For His Love Of Alcohol

Wikimedia CommonsPerkeo of Heidelberg was a cup-bearer to Prince Charles III Philip.
Perkeo of Heidelberg was born Clemens Pankert in 1702, and like many other jesters of the age, he was a dwarf. Fortunately for Perkeo, his short stature and sharp personality enabled him to fall into the good graces of Prince Charles III Philip of the Holy Roman Empire. Perkeo was brought to Heidelberg Castle as a teenager to work as the prince’s jester and cup-bearer.
It was in Heidelberg that Perkeo earned his moniker. According to the official website of Heidelberg Castle, Perkeo was rather fond of wine. Any time someone asked if he’d like another glass, he would respond in Italian, “Perché no?” which translates to: “Why not?”
Historical accounts claim that Perkeo drank anywhere between five and eight gallons of wine each day, and legend had it that he could empty the entire Heidelberg Tun, which held over 200,000 liters, in a single gulp. Ironically, he was also in charge of keeping track of the castle’s wine stocks.
Perkeo impressed the court with his various antics, pranks, and jokes — so much so that he has, in a sense, become the unofficial mascot for the town, with multiple statues of his personage decorating Heidelberg.
One popular legend says that Perkeo wound up living well into his 80s only ever having drunk wine until one day he fell ill. The story goes that a doctor instructed Perkeo to drink some water — and he died the next day.
