It is well known that I have a taste for somewhat racy gangsta jokes , and this sort of joke can easily go over the wrong way. After all, there are few people more conspicuously white as I am, to the point of caricature, to the point of making Dynamite Hack look like real boys in the hood. This is not an exaggeration. Yet despite my love of self-caricature, it is not entirely in mocking, and it is certainly not meant to be disrespectful to anyone with far greater street cred than I possess, like the members of PM Dawn . Part of the necessary context is that I spent a considerable amount of my life, as a high school student in East Tampa and then as a college student in South Central Los Angeles, living in the ghetto. If I am tragically unhip white boy, more white than Dan Hartman , I am someone who has actually lived in relatively hip areas, and lived there under the same conditions as my neighbors dodging bums and irritated at the cops as well as the less than particularly bright drug dealers who assumed that white people were potential customers and not neighbors.
The context we put to comments is a big part of what determines how we view a given comment. More than most people, I think I require a great deal of context. This has not always been to my benefit. Anyone who has shared more than a few dinner conversations with me, and given my love of social eating, this is a fairly large group of people, has likely seen at least a few examples of my razor sharp wit, with my native skill at figuring out the most awkward thing to say and then zinging on it like a laser-guided missile. I have had cause to lament these witty comments on many occasions , especially because I usually end up poking far more fun of myself with my wit than I poke fun of anyone else around me, and the fact that my wit often pokes at my own sensitivities and preoccupations, few of which have done me much credit with other people, some of whom are just as sensitive as I am, and not nearly as witty in response. It is not charitable to engage in a duel of wits with unarmed people.
Wit has been one of the casualties of our culture’s slide towards immense self-seriousness. Wit requires a certain amount of ironic distance from ourselves, a realization that something is crying out to be said, even if, like many an ill-timed rapier thrust, it exposes us to a fair share of ridicule in turn. Sometimes things need to be said, even if the only people who can say them are wildly inappropriate at doing so, and they should be told in the funniest way possible, because there are some truths that can only be told as a joke because they are too serious to talk about any other way in polite company. There are plenty of people, of course, who would argue that my company is not polite company, but if I sometimes struggle to be polite company, largely because my wit is frequently directed at the unexamined premises and ironies and contradictions of the people around me, I at least appreciate polite company. At least I appreciate company that is polite enough to smile and laugh at my attempts at wit, and not to be offended by them.
What is the context that helps us to understand someone’s behavior? Sometimes, in order to properly understand someone or something, we need to understand something of a person’s biography and background, something of a person’s drive to use humor and wit as a defense against the injustice and absurdity of life, and as a way that terribly serious people sometimes seek to take life just a bit less seriously than they would otherwise be inclined to do, to make a joke in order to feel less awkward. If one felt as awkward as I did on a regular basis, they would likely be every bit as witty. Of course, it is hard to give others credit when it comes to the context that they need to be properly understood. Because we know ourselves better than we know others, unless we are spectacularly unobservant, we are aware of the sort of context that others need in order to respond to us appropriately. If we are charitable people, we will give them that context, and if we are fortunate enough, others may even return the favor to us, so that we may have the context that we need to understand those we are around, and who are often the unfortunate victims of our witty barbs and lighthearted jests.
 See, for example:
 See, for example: