Diogenes had a weird sense of humor. Examples:
1. Legend has it he took to carrying a lamp in broad daylight, to assist in his search for one honest man.
--From the first I did not understand the point of the lamp. It sounded cool, but I wondered the significance. Many years later I have a theory. With his lamp in daylight Diogenes says maybe it's the sun's fault. Maybe I am not finding the honest men due to the failure of the sun as an adequate light source. Therefore look, a lamp. Just in case that big huge SUN is not enough I've got this candle-lamp here. I brought it myself. The Sun can create conditions that are overly light, and to solve that crisis Diogenes decides he should introduce more light. He's been driven to madness. He doesn't know night from day, and he's so desperate in his search for one honest man he'll try anything. That's the joke. The lamp is a piece of early observational humor of the absurd, silent humor, and there's a certain decadence to it we don't expect from such ancient times.
2. Responding to Plato's definition of man as a "featherless biped," Diogenes plucked a chicken and put a sign on it saying "this is Plato's man."
--A hilarious gesture, my personal favorite. Because of the pure ridicule of it. Diogenes is a philosopher with nothing but contempt for "philosophy." By accepting an authority position, Plato violates Diogenes' anti-authority absolute. The plucked chicken transcends Diogenes' reactionary motivations. The message it sends is strange and beautiful: be anti-smart in a smart way. The whole magic of Cynicism comes through in the plucked chicken. Be creative in your reactions. Express your contempt imaginatively, humorously. Let contempt inspire you. Let disgust bring a smile. "Knowledge" is a game - a failed, deformed religion, not worth pursuing or loving. The clever definitions handed down by authorities (like Plato) are usually wrong and easy to make fun of.
3. Diogenes "would praise those who were about to marry and refrained, those who intended to go on a voyage and never set sail, those who thinking to engage in politics do no such thing, those also who purporting to raise a family do not do so."
--They were tempted but did not conform. They conquered conformity and therefore earn Diogenes' praise. Marriage and family, even travel, are the adjuncts of a required moral attitude. Diogenes rejected any required moral attitude in favor of a comically negative attitude, which became known after him as Cynicism. Impulsive rejections, dramatic mood shifts, the sudden abandonment of life-long goals -- all encouraging signs of independence and attitude for Diogenes. Why would he praise impulsive rejectors? Because an impulsive rejection is the dramatic expression of distrust, both in yourself and in life. You don't trust yourself as a desirerer, a goal-setter. You realize you don't know what to want. You're sick of wanting, sick of reaching out. You finally see the truth and you act on it rather than ignore it. You act to change your direction away from the lie. The end of trust is the beginning of honesty. That's funny to Diogenes.
Cynicism is a style of protest against a certain kind of human dishonesty. The cynic does not deny that to lie is part of the nature of humans as products of biology. There are obvious survival ramifications. We lie to survive socially. With our lies we self-protect. So the cynics don’t moralize against lying wholesale. It’s more they object to a certain lying style. The problem is the stupid lying, the dishonesty of a man who cannot face his dark side, who cannot admit the pushes and pulls of his own nature or keep them in mind when judging others. Stupid dishonesty, all it does is deny. It does not create. Smart dishonesty is smart because it is creative. Smart dishonesty is acceptable.
But don’t be fooled by this instance of moral relativism into thinking there is not a basic moralism behind the cynical view of the world. There is. The cynic self-righteously thinks: ‘I am good because I don’t trust myself. My wisdom tells me I should not trust myself. Only fools trust themselves.’ In any society that stance puts the cynic in direct conflict with the system, because the system can only work if people do trust themselves, do believe and behave as if they deserve to have whatever they happen to want at any given time. People at large must operate according to the thinking which states: to question one’s desires is stupid.
As a term, cynicism can be erroneously applied. The intelligent use of stupidity, such as by politicians, corporations and advertisers, does not qualify as cynicism. In my view, the intelligent use of stupidity is simply stupid, not cynical. I both love and hate the quote: “No one ever went broke underestimating the intelligence of the American people.” I love it because it is true and hate it because it is not false.
Cynicism is the high road. Those who reject it identify themselves as low. As a society we can get to a point where we don't think we can get any more cynical, but we won't be cynical enough.