Prince Paul, basically hip hop's first satirist, dropped his first solo album/project in the mid 90s called Psychoanalysis: What is It?. This song "Beautiful Night", a darkly comic ode to date rape and homicide, is essentially a hip hop version of Brett Easton Ellis "American Psycho": An average negro-joe is blithely confessing his recent crimes to his psychiatrist over a beat; all of a sudden you're laughing at stuff you're not supposed to be laughing at.
Hip Hop has largely missed the 'black comedy' boat because for most of its history the socio-political-cultual obligations made making the kind of fun that cuts deep difficult. Black people had a tough enough time trying to catch up in America without the potential karmic backlash via songs that coo about it being "a beautiful night for a date rape, a beautiful night for a kill."
It's one thing to kill for survival, or to sell drugs to feed your kids. It's another to make jokes about it all. That sensibility can only come about once you're no longer fighting for survival, and you've reached a certain comfort level... I suspect I was able to appreciate/indulge this sort of art in part because I was off in my bougie insular prep/boarding school environment. Prince Paul and De La were hip hop comedy gold for the slacker hip hop heads in prep school.
Eminem was able to get away with this sort of thing (think '97 Bonnie and Clyde) in part because he inhabited that crazy-white-boy space. But maybe now, post-Obama, crazy-black-boys will be able to get their rocks off too.[ listen to the song on TAN3000]