Legend states Alexander the Great asked Diogenes if he could give the philosopher anything. Diogenes, who had nothing, responded, "You could move away out of the sun and not cast a shadow on me." Alexander supposedly replied, "If I were not Alexander, I would be Diogenes."
Diogenes lived in "a burial urn" (big clay tub) and his father counterfeited coins. However, Diogenes confessed to the crime. The exact details remain uncertain.
Diogenes had many interesting anecdotes. "Seeing a child drinking from his hands, Diogenes threw away his cup and remarked, "A child has beaten me in plainness of living." When invited to the house of Plato, he trampled upon his carpet, saying that he thereby trampled on the vanity of Plato."
Diogenes had a unique view on life. Sold as a slave, he pointed and said, "Sell me to this man; he needs a master." The man heeded the advice, and entrusted Diogenes with his household and the education of his children.
It is said that Diogenes sometimes walked around with a lamp in broad daylight. When asked why, he replied, “I am looking for an honest man.”
Diogenes was in Corinth when Alexander the Great sent word through a messenger asking Diogenes to come see him in Macedonia. Diogenes replied that if Alexander wished to see him, Alexander should come to Corinth.
When asked how to avoid the temptation to lust of the flesh, Diogenes pulled out his penis and began masturbating. When rebuked later about it, he replied "If only I could sooth my belly by rubbing it."
"When Plato gave Socrates' definition of man as 'featherless bipeds' and was much praised for the definition, Diogenes plucked a chicken and brought it into Plato's Academy, saying, "Behold! I've brought you a man." After this incident, "with broad flat nails" was added to Plato's definition."
Diogenes was fiercely opposed to institutional organizations. He was also famous for having a poor moral compass and abandoning all sense of decency.
Diogenes the cynic played two roles in society. He was reviled by society, but also an object of desire.