Diogenes of Sinope was an ancient Greek philosopher who, at different points, allegedly lived in a wine barrel (some accounts describe it as a tub), urinated on guests at a banquet, defecated in the theater, lived on a diet of onions, and was one of the few people who openly mocked Alexander the Great and stayed alive.

Although some believed him to be absolutely crazy, Diogenes was also one of the most respected and loved philosophers of the 4th century BCE, and one of the most famous founders of the ancient Greek school of philosophy known as Cynicism.

A lot of speculation surround the life of this controversial philosopher, since he left behind no first-hand accounts of his own life, or if he did, they’ve since been lost. And his larger than life persona probably produced many legends and tales. Nevertheless he is considered a very influential figure in philosophy.

Diogenes was born in Sinope (a city on modern-day Turkey). His father used to work with minting money, and Diogenes joined his father later on and began working with him. But they found themselves later on in a dispute with the law, after Diogenes (or his father, or both of them) began defacing money.

While some historians believe the motivations were purely political, others think the act may have been the result of an incident involving the Oracle of Delphi. Either way, Diogenes then fled Sinope, and headed to Athens.

In Athens, Diogenes took up somewhat of an unconventional way of life, and made it his mission to metaphorically deface the coinage of custom and convention, which he maintained, were simply lies used to hide the true nature of the individual.

Diogenes allegedly met Antisthenes in Athens who at first refused him as a student but, eventually, was worn down by his persistence and accepted him. Like Antisthenes, Diogenes believed in self-control, the importance of personal excellence in one’s behavior (in Greek, arete, usually translated as `virtue’), and the rejection of all which was considered unnecessary in life such as personal possessions and social status.

Diogenes started living in a barrel (some describe it as a jar, others as a wine cask or tub) at the Temple of Cybele. He got rid of his belongings, and maintained a diet of just onions. One day he saw a child cupping his hands to drink water, after that he threw away his own cup, remarking something along the lines of “A child has beaten me in plainness of living.”

The philosophy of Diogenes was more than just an ascetic movement, he didn’t just renounce possessions; he preached obscenity, broke taboos, viciously attacked customs, and was relentlessly rude. For he considered, honesty to be a key value, and he saw Athenian customs and manners as a form of lie.

Many accounts depict him walking the streets with a lantern and shining it into the faces of passersby, apparently looking for an “honest man” or a “human being”.

Diogenes believed any act that was considered natural and acceptable in private (like urination and defecation), should also be considered natural and normal in public. he famously ate in the market place, something considered a taboo in that time, and when asked about this act he replied, “I did, for it was in the market-place that I was hungry.”

Diogenes could be considered in the terms of our day as a huge troll, a philosopher who used wit and mockery to challenge tradition, and prominent figures of his time. In one instance, after Plato had given Socrates’ definition of man as a “featherless biped” and was very much praised for that definition. Diogenes plucked a chicken and brought it into Plato’s Academy, and said, “Behold! I’ve brought you a man.” After that incident, “with broad flat nails” was added to Plato’s definition.

On another occasion, a group of wealthy Athenians at a banquet began throwing bones at Diogenes, insulting him and calling him a dog. Diogenes then responded to this by lifting his leg and urinating on the banqueters.

Diogenes was often associated with dogs. He believed that human beings had much to learn from studying the simplicity of dogs, which, unlike human beings, had not ‘complicated every simple gift of the gods’. The terms ‘cynic’ and ‘cynical’ derive from the Greek kynikos, which is the adjective of kyon or ‘dog’.

Diogenes’ trolling and witty mockery weren’t just targeted at fellow philosophers and public figures. In which we remember one of the most discussed anecdotes in philosophical history, the meeting of Diogenes and Alexander the Great.

Word of Diogenes’ wisdom and peculiar ways reached the greatest military leader at that time, Alexander the Great. As a child, Alexander was tutored by Aristotle, and when he became a grown man he was learned man. But wisdom is addictive, and Diogenes intrigued the young commander.

Philosophers, and public figures used to come out to see their king and to offer him praise, gifts, and compliments. But Diogenes preferred to stay in his barrel, far away from this life. So Alexander decided to visit the great philosopher himself.

On that day, Diogenes was laying in the sun, enjoying the sunlight, when he heard movements of a large crowd, and trumpets signaling the arrival of a great man. Diogenes looked up, and saw Alexander with a number of his guards. He raised himself up a little when he saw so many people coming towards him, and fixed his eyes upon Alexander. Alexander greeted Diogenes, and praised his wisdom, then asked him if he wanted anything, in which Diogenes responded, “Yes, stand a little out of my sun”.

Alexander was shocked, but then laughed and said, “But truly, if I were not Alexander, I would like to be Diogenes.”

After spending years in Athens, Diogenes ended up in Corinth. According to a story which seems to have originated with Menippus of Gadara, he was captured by pirates during a voyage to Aegina and sold to a wealthy Corinthian named Xeniades. When asked if he had any skills, Diogenes replied, “That of governing men.” Xeniades liked Diogenes’ response and made him the tutor for his sons, and eventually Diogenes became like a member of the family.

Diogenes lived the rest of his days in Corinth, where he continued to live a life of poverty and simplicity. Although most of the accounts of him living in a barrel appear to be in Athens, there are some accounts of him living in a jar near the Craneum gymnasium in Corinth.

Just like his entire life, Diogenes’ death is also riddled with mystery and a matter of debate. He is alleged variously to have become ill from eating raw octopus, holding his breath until he died, or to have suffered an infected dog bite, but it is more likely that he died of old age.

Although Diogenes had requested his remains be thrown to wild beasts, his friends and admirers insisted he should receive a proper burial. A marble pillar and a statue of a dog above his grave.

We could learn a lot from this great peculiar philosopher, especially in a time and society filled with complexities and hardships.