most people say clayton bigsby is Chapelle's best skit, I counter that the nigra family is his magnum opus, 2 scenes come to mind, when the father is informed that his daughter is going out on a date with lil timmy, he opposes it, his facial expressions, on the other hand, reveal the love and concern he has for the path his daughter has chosen, his denounciation is not founded on anything personal but on the societal mores of that era. (a scene that many interracial couples may be familiar with).
The other is the restaurant scene, more specifically when Chappelle proclaims, "this racism is killing me inside". The statement speaks for itself, although it can also be viewed as something said out of character since the whole skit is rather jarring and Chappelle was simply projecting how he felt about the sketch. Which might be a microcosm of his implosion...but i digress.
The Nigra Family sketch perfectly encapsulates America's inability to correct its 'original sin'. Majority of white America is not racist, they just dont have the fortitude to eradicate the racist elements in their culture. Although black America have been resolute against all odds, it is hard to deny the fact that racism, as Lupe would say, hurts the soul.