I used to be into my hip-hop a few years back but not so much now. I'm still an expert though

Jay-Z is okish. But really is just one of the better commercial artists. There are far far better artists out there.

try a few of these -
Non - Phixion (listen to the track 'black helicopters').
Jedi mind tricks (check out album 'violent by design')
Saul Williams
Anit-pop consortium

And for a bit of lightweight but infectious student hip -hop its got to be Jurassic 5.

Miles, i'm not impressed. I thought you were a man of the world. Sure, acts like 50cent etc are crass and boring as sin, but there is a whole wealth of really good underground stuff. Intelligent people making intelligent music and not a single mention of hoes or guns.