Many years ago, I learned a method to ease tense situations. Make fun of yourself. This was effective for breaking the ice in sales situations, lightening up the mood, and getting things moving. It is currently presented as an effective tool for public speaking because it eases tension between the speaker and audience and puts you at their level. This is a staple of stand-ups, think Louie Anderson, Chris Farley, and Woody Allen.
I do not denigrate the caliber of their comedy to state these three never reaped the quantity of hot women as a Charlie Sheen.
I noticed a couple weeks one day that self-deprecating humor was not working for me any more in work situations, and it clicked for me because half of the people that work for me in my department are women and the balance are feminized men. So my Delta buzzer went off and I changed gears. Now I go straight into a self-deprecating joke, but instead of my usual subject, I pick my most difficult employee that week and throw him or her under the proverbial bus.
Employees are acting more respectful and the women's eyes glisten that they have a department led by a man. Score! Work issue solved by Game.
To back up my anecdotal results I have been watching natural alphas. I can't find very many of them doing any self-deprecation, and if they do it is slight and often combined with throwing someone else under the bus. Self-deprecation is not to be confused with a roast or a guest spot with late night host pimping a new movie. Both of these, by design, give the mark such a large quantity of social credibility that they can spend it like a lambda wearing tights in boys-town.
I believe you can still use self-deprecating humor in setting social sexual hierarchy, but sparingly and under the two following conditions:
1. You must have plenty of social capital to spend.
2. It must be delivered in a manner that leaves no doubt as to you being on top.
Robert Orben said it best. “Self-deprecating humor should always be two-pronged. It should comically acknowledge a criticism or situation, but also infer that there is no substance to it and that you are in the driver's seat.”
For those of us still learning game, self-deprecating humor is not a great tool.