The Transplants! Oh my god the Transplants.
Gangsters and Thugs is practically written for a runner crew with roots in the barrens. (Video is actually pretty Shadowrun, go-gangs and all.)
Diamonds and Guns is also worth checking out, really, everything they've done has the feel I think you're looking for.
For hip-hop, Kanye West's
Monster is basically four people talking about being bad guys, and one in process of becoming one. Really, the whole album (My Beautiful Dark Twisted Fantasy) is solid for this kind of thing.
For a street-level runner trying to pull off hooding, there's always Goldfinger's
SupermanAnd while we're at it, NOFX's
The Man I Killed is actually extraordinarily Shadowrun in its way.
Blue Stahli's
Enemy is a spectacular "And now we are Shadowrunners" song, heck, most of his music would fit in-universe pretty well.
Ultranumb is a pretty solid counter-culture runner song.
Hope that helps!
