Cleopatra wasn't just a woman of renowned beauty and charm who was later immortalized on the silver screen in a memorable portrayal by the legendary Elizabeth Taylor. Cleopatra was the last pharaoh of Ptolemaic Egypt—during which she established a steadfast and powerful alliance with Julius Caesar—spoke nearly a dozen languages, and was schooled in math, philosophy and astronomy. She also sounds like she was a lot of fun to hang out with.
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In 41 B.C., Cleopatra and her lover, Roman general Mark Antony, started a club called "Inimitable Livers"—which is widely understood to "have been a group dedicated to the cult of the mystical god of Dionysus," but which some have "interpreted as an excuse to lead a life of debauchery." According to the History Channel, though, Inimitable Livers was a drinking society and "the group engaged in nightly feasts and wine-binges." Antony and Cleopatra were also known to be avid goofballs, spending many evenings "wandering the streets of Alexandria in disguise and playing pranks on its residents." If they were still alive today, we bet they'd have a thriving YouTube presence.
Cleopatra was also fond of playing clever tricks on Antony. According to a 1957 paper published in The Classical Journal, a story recorded by Pliny the Elder in Natural History around the year 77 A.D., about 100 years after its alleged occurrence, describes a bet Cleopatra made with Antony that she could spend "10,000,000 sesterces" on one dinner (that's a lot of money—estimated to be anywhere between $10 million and $20 million in modern currency, though it's impossible to determine the exact conversion). After ordering up a totally conventional meal, Cleopatra had one of her servants bring over a cup of strong vinegar. She dropped one of her priceless pearl earrings into the solution, waited for it to dissolve—"into slush," according to the original text—and drank it.