He had alot of talent not just as a rapper but as an artist. I think he went out of his way to personify what being poor and black in America was. By doing this he could gain credibility among his peers and get them to listen to what he was saying. Kinda like, you got a be a thug to to talk to one and get them to understand. Not all of his stuff was like "hit 'em up". Take the movie "Juice" for example. Its a movie about a basically good kid that due to forces around him goes nuts. I think that's part of the message he's trying to convey. That without changes in social structure, things are always going to be the same and that you're gonna keep turning out the same type of situation from the inner cities generation after generation.
"instead of a war on poverty
they got a war on drugs so the police can bother me
And I ain't never did a crime I ain't had to do
Now I'm back with the facts bringin it back to you"