5 Sharp Quotes From Diogenes, the Funniest Ancient Greek Philosopher

Let's set the scene here. Diogenes, a penniless philosophizing beggar, is lazing around in the sun when he's approached by Alexander the Great, the most powerful man in the known world. Alexander makes Diogenes an incredible offer — ask anything of me and I'll give it to you. Diogenes could have asked for gold, for a mansion, or for a cushy position in Alexander's court.

But instead, Diogenes grumbles (without opening his eyes, we imagine), "Stand out of my light."

Did Diogenes dislike Alexander? We don't know. But what we do know is that Cynics like Diogenes prized one thing above all else: autarkeia, a Greek word that roughly translates into autonomy or freedom. And Diogenes knew that a "boon" from Alexander wasn't just a gift, but an attempt to buy his loyalty.

"When you're indebted to a politician, a statesman, or even more so the emperor, you have lost your ability to speak freely and act freely," says Piering. "So not only does Diogenes not need anything from Alexander the Great, he doesn't want anything from him."

You might think that insulting an emperor would get you in trouble, but Diogenes enjoyed a strange type of immunity as a "comic" figure and even posh Athenians had a grudging respect for Diogenes' unencumbered freedom. According to Diogenes Laertius, the mighty Alexander is reported to have said, "Had I not been Alexander, I should have liked to be Diogenes."

Bonus: "When someone was extolling the good fortune of Callisthenes and saying what splendour he shared in the suite of Alexander, 'Not so,' said Diogenes, 'but rather ill fortune; for he breakfasts and dines when Alexander thinks fit.'"

Diogenes' biography is sketchy at best, but we know that he was originally from Sinope, an ancient city located in Turkey on the shores of the Black Sea. He was exiled for defacing the local currency (or maybe his father did it; it's unclear) at which point he relocated to Athens and became a student of Antisthenes, perhaps the first Cynic philosopher.

In a later episode, Diogenes was captured by pirates and auctioned off as a slave in Corinth. As Piering explains, captives like Diogenes would have been put on the auction block and asked to list their skills to potential buyers. A warrior might be sold as a bodyguard or a skilled cook as a chef.

When the auctioneer asked Diogenes "in what he was proficient," according to Diogenes Laertius, the mischievous philosopher replied, "In ruling men." Kind of an odd thing for a slave to say, but Diogenes persisted. He spotted a rich man in the crowd named Xeniades and said, "Sell me to this man; he needs a master."

Again, Diogenes used a witty exchange to say something about the nature of freedom. Even as a slave, Diogenes was freer than his supposed master.

"Diogenes makes it clear that he's the master in that relationship, not the person who bought him, just like he's more free than Alexander the Great," says Piering. "It's the first time in the history of Western philosophy that you get this really radical conception of freedom. You don't see that in Socrates, Plato or Aristotle. It really starts with the Cynics."

Bonus: "Someone took [Diogenes] into a magnificent house and warned him not to expectorate, whereupon having cleared his throat he discharged the phlegm into the man's face, being unable, he said, to find a meaner receptacle."

To give the whole quote: "Plato saw [Diogenes] washing lettuces, came up to him and quietly said to him, 'Had you paid court to Dionysius, you wouldn't now be washing lettuces,' and that he with equal calmness made answer, 'If you had washed lettuces, you wouldn't have paid court to Dionysius.'"

This quote needs some context. First, remember that Diogenes lived on the streets and slept in what's sometimes called a "tub," but what was really a pithos, a large ceramic jar for storing grain or wine. In Athens, only beggars and dogs ate in the marketplace, and only the lowliest of creatures dug through the trash for scraps.

So here he was, washing off some discarded lettuce in the market, when the great Plato deigned to give the lowly Diogenes some career advice. If Diogenes sucked up to a powerful ruler, like Dionysius of Syracuse, then he'd have the means to live in a real house and not have to scrounge for food in the streets.

The irony is that Plato did travel to Syracuse to take the difficult job of teaching moral philosophy to Dionysius, a hard-partying tyrant who wasn't receptive to Plato's message of moderation. He not only fired Plato but sold him into slavery. So why would Plato suggest that Diogenes do the same?

Piering explains that Plato was aristocratic or at least in the thrall of the ruling class. He believed that the best thing a philosopher could do was attach himself to a powerful person or family. Diogenes believed the opposite.

"Instead of relying on a ruler to pull you out of poverty, Diogenes says to accept poverty and you'll be free from these bloody rulers," says Piering. "It really highlights the difference between the two."

Bonus: "Plato had defined Man as an animal, biped and featherless, and was applauded. Diogenes plucked a fowl and brought it into the lecture room with the words, 'Here is Plato's man.'"

This was Diogenes' response when he was asked what he had done to earn the nickname "the Dog." It seemed to be a popular insult that Athenians threw at him, which he turned around and embraced.

But Diogenes may not have been the first Cynic to be called a dog, or kuōn in Greek. Piering writes that his teacher Antisthenes earned the nickname Haplokuōn, meaning "a dog plain and simple," for his own allegedly rude and crude behavior.

In fact, our word Cynic was likely derived from the way that most Greeks felt about mongrel philosophers like Antisthenes and Diogenes. They were kunikos or "dog-like." If you replace the Ks with Cs, you can see how kunikos became cynic. (The word "cynical" didn't take on its modern meaning as "negative and pessimistic" until much later.)

Bonus: "At a feast certain people kept throwing all the bones to him as they would have done to a dog. Thereupon he played a dog's trick and drenched them." (Spoiler: It wasn't water.)

This is one of the most famous stories about Diogenes, although his quote is often reworded to say, "I'm looking for an honest man." Piering says that the original Greek words say nothing about "honest" or even a "man." It says simply that Diogenes was looking for "a human being."

Lighting a lamp in the middle of the day and wandering the crowded streets of Athens in search of a "human being" is a type of performance art that Diogenes was fond of, says Piering. In another episode, Diogenes was seen begging money from statues. When asked why, he replied, "To get practice in being refused."

What was the point Diogenes was trying to make with his lamp-in-the-street performance? To Diogenes, being worthy of the category "human" demands virtue, says Piering. And virtue doesn't mean the same thing to the Cynics as it does to Socrates or Plato. A virtuous human, for the Cynics, acts exclusively in accord with nature and in accord with reason.

At the heart of Diogenes' philosophy, and therefore his comedy, is the stance that the people of Athens — who walk around worrying about money, power and social conventions — are the real "madmen." He's the only reasonable human being in sight.

Bonus: "Most people, [Diogenes] would say, are so nearly mad that a finger makes all the difference. For, if you go along with your middle finger stretched out, someone will think you mad, but, if it's the little finger, he will not think so."