Originally Posted by nico

Aesop Rock, Atmosphere, Blueprint, Dilated Peoples, Immortal Technique, Mos Def, Sage Francis would all fit what you're looking for. They have meaningful lyrics, and plenty of songs that seem personal or real.

Albums i'd recommend in no particular order are:

Soul Position (RJd2 and Blueprint)
Labor Day - Aesop Rock
God Loves Ugly - Atmosphere
Overcast - Atmosphere
Personal Journals - Sage Francis
Revolutionary 1/2 - Immortal Technique
I wish my brother george was here - Del the Funkee Homosapien
Deltron3030

There are a ton of other good hiphop artists out there who don't sing about the usual bullshit you hear on the radio, it just takes a while to find some of the better ones. Try and check some of the stuff out I listed and post if it's what you were looking for, if not I can recommend some more and we'll see if it matches.