Although I don't like the streets, this dude reminds me of that garage type stuff. It's extremely witty, simple but cool beats, some good samples and funny social commentary.
Maybe Eminem meets the Streets?
And best of all, his album is available for free on his website! Tim Fite
Hmmm... I do disagree with you on himself thinking that he's being extremely witty, I don't think it comes off as him being superficial. The whole thing feels like a joke and that's kinda why I wind up taking it seriously.. if you can make sense of that.