A few from the 90's, the era of gangsta rap and hedonistic music videos. Warning: most of these are pretty misogynistic. It comes with the territory, part of the interesting thing is the talent is there, but slightly misguided.
Del the Funky Homosapien - MistaaDobalina
http://www.youtube.com/watch?v=dFieSQHmQT0Craziest sh*t I ever heard when I was a kid. This guy was Ice Cube's cousin, made music that was a little different than what you usually heard. I'm way to white to understand whatever he's talking about, but I always liked it.
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If you never listened to Ice Cube's early music, he was a walking contradiction. Born in L.A., raised fairly middle class, graduated from college... then was hired to write Lyrics for Eazy E's NWA. So he was able to create this entire image where he hated white authority, he was talking about all the poor people growing up in the ghetto even though he didn't know a THING about that.
Here's "Alive on Arrival" from "Death Certificate". Entire song tells the story of getting shot then trying to get somebody at the hospital in the hood to help him
http://www.youtube.com/watch?v=qK-Fsg3U6QQ---------------------------------------------------------------------
Luniz - I Got 5 On It
http://www.youtube.com/watch?v=lhhSd9q_wZk1995, this is probably one of the best examples of the whole keyboard based hiphop that came out in the 90's. Fantastically good for a rap song. The video's hilarious. I wish I was there.
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Big L - No Ends, No Skinz
http://www.youtube.com/watch?v=bQ0u2jjXs_oIncredibly talented rapper, shot and murdered a couple years after this for basically nothing, another example of someone with plenty of talent who got mixed up in some idiocy and paid for it with his life. Basically his brother was in prison, pissed somebody off, they saw Big L. in a car and killed him. This guy was probably one of the most underrated ever, lots of people have never heard of him and he was only around for a short while. In the song he talks about beating women and celebrates that. Another example of someone growing up with no father, had plenty of talent and could have been successful at whatever he chose but ended up misguided in practically every area of his life. Such a shame.