Diogenes of Sinope occupies a a unique place in world history. One of the first Cynics of ancient Greece, and a large influence on the Stoic philosophy. The context and events of his life remain largely unknown.
Plato is said to have labeled him "Socrates gone mad." Robin Hard writes in the introduction to Diogenes the Cynic: Sayings and Anecdotes with other popular moralists, "It was a commonplace of Socratic thought that one can be rich by being satisfied with little... Diogenes radicalized this idea, taking it to the utmost extreme." By ignoring the cultural and social norms of society, and indeed, civilization in general, he was "content to satisfy those needs in the simplest and most direct way possible..." To the point where materialistic needs become completely unnecessary in his radicalized philosophy.
On the surface, Diogenes would appear to be the greatest troll in history, a purveyor of misanthropic values. One common anecdote about him states he "masturbated in the marketplace one day and said, 'if only one could do away with hunger by rubbing one's stomach.'" One could assume he did this in his residence, a large glass jar in the middle of an Athenian marketplace. Diogenes did not withdraw from society, but critiqued it from within in a shockingly blunt swagger, and a biting wit.
He sought to go against the flow, both figuratively and literally, as another anecdote has him walking into a theater as everyone was walking out, directly through the foot traffic. When asked why he was doing this, he remarked "this is what I seek to do my whole life through."
Diogenes lived off of the generosity of the people, but never considered himself a "beggar." He considered the philosophical insights he had to teach well worth the exchange. One of the most interesting stories about him depicts him roaming the streets of Athens, holding a lantern up to the faces of people, and claiming he was searching for a honest man. His reputation was so strong in ancient Athens that it is said that Alexander the Great approached him, asking if there was anything he could do for the philosopher. Diogenes asked him to move, as he was "blocking his sunlight." How did he gain such notoriety and reputation that this tale may be considered true? He stated "by holding reputation in contempt."