Semisight beat me too it.
Lupe IMO is head and shoulders above everyone else. 80% of what he says goes over people's heads.
Aha. Yeah, Lupe is kinda nice, never really listened to too much of him. He showed great skill with "Kick Push" which was a song about skating BUT it was open to interpratation. I thought it was about passion, others thought it was about skating other thought it was about drug dealing. That's real nice. lol
Kick, Push was a single. You need to hear some of his stuff that isn't as mainstream, if I can even use that word and Lupe in the same sentence.
Check out: Failure, I Gotcha, Lupe The Killa, Streets on Fire, Game Time, Yoga Flame, Say Something. I can really go on and on.
Other than that some of my older favorites are:
A Tribe Called Quest
and some newer guys that have shown they have what it takes: