Dr Zoidberg
Why not Zoidberg?
Probably the smartest "kid" in regards to art and/or music. Also, for hip-hop try Aesop Rock's Skelethon Album. If you want more hip hop recomendations or to just discover a new album on a day to day basis...just watch the needle drop on YouTube.
Thanks for the kind words and recommendations! I'm really enjoying Aesop Rock thus far.