I hope reposting wikipedia is acceptable for the purpose of stimulating discussion.
Quote:In philosophy and internet tranny sociology, the cool nigger paradox or cool nigger's paradox or antinomy of the cool nigger is the statement of a cool nigger that they aren't caring: for instance, declaring that "I'm not mad" If the cool nigger really didn't care, then he wouldn't feel the need to express how little he cared, which means the cool nigger in fact just cared. In "I'm not mad, you dumb nigger" the paradox is strengthened in order to make it amenable to more rigorous sociological analysis. It is still generally called the "cool nigger paradox" although abstraction is made precisely from the cool nigger making the statement. Trying to assign to this statement, the strengthened cool nigger, a classical binary truth value leads to a contradiction.
If "I'm not mad, you dumb nigger" is true, then the cool nigger really isn't mad, but the sentence includes the n word, which isn't cool (ed: nigger), and therefore the cool nigger is not cool. Further, not caring what a cool nigger would think is cool is the most extreme form of not caring, which would imply the cool nigger is not only cool, but the coolest.