1. Winston Churchill
Churchill never held his tongue and never spilled his drink, and was proud to be a bit of a Joker in a country that was more used to Kings, Queens and Jacks.
2. Henry The 8th
Henry the 8th was charming, curious, educated, and wasn’t afraid to do things his own way—to the frustration of a great many in the church.
3. Benjamin Franklin
Benjamin Franklin was a Founding Father and invented bifocals. The women loved him and the French loved him. Plus his first name is a synonym for money, because he’s on the $100. Not bad for a guy who started off as a newspaper printer.
6. Allen Ginsberg
Ginsberg was a passionate poet who played fast and lose with language and was comfortable enough to stand against repression, violence and meaningless materialism.
7. Teddy Roosevelt
Few other presidential examples can come close to how chill ol Teddy was with himself. When he wasn’t winning the Spanish-American Way, running the Navy, and founding his own political party (the Progressive “Bull-Moose” Party), he was touring Europe and Africa and hunting every badass animal that came his way. He wasn’t messin’ around.
9. Nikola Tesla
Tesla was so chill that he didn’t even care that most of his inventions and contributions to electronics weren’t recognized until the 1990s, more than fifty years after his death. Anyway, he never married and rarely hung out with anyone, which is pretty much the definition of being comfortable with yourself. So comfortable that he didn’t need anyone else.
10. Ghengis Khan
Ghengis practically took on foes in his sleep—but given the hundreds (and ultimately millions) of children he fathered, it’s doubtful he was getting much of that anyway. Who needs it when you’ve decided that you’re going to establish one of the largest empires in history? He was just being *himself*.
Socrates was clearly a bigtime chiller. You don’t casually come up with some of the founding ideas of Western philosophy without knowing how to just sit back and relax, thinkin’ about stuff. It just so happens that the kind of things Socrates was chilling on were like, super important.
12. Joseph Ducreux
Ducreux was a prominent portraitist in Louis XVI’s court. That’s pretty all right on its own, but the reason why Joseph was totally comfortable with himself is that he didn’t let anyone else tell him how he’d do his paintings. He liked to paint people making unique expressions, much more casually than they typically were. He’s also a meme. So.
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