Reddit mentions of Knowledge Reigns Supreme: The Critical Pedagogy of Hip-Hop Artist Krs-One (Transgressions: Cultural Studies and Education)

There's a ton of stuff for you to work with. Something super old school --> https://www.youtube.com/watch?v=O4o8TeqKhgY

Not as old but still old but timeless in its political message --> https://www.youtube.com/watch?v=8PaoLy7PHwk

Still old, super classic all around, and a tribute track to a fallen friend. --> https://www.youtube.com/watch?v=FiOcVWQY2bc

KRS-ONE can't hurt, dude coined the term edutainment as far as I know. https://www.youtube.com/watch?v=d6svkdJ7HDo

Pharoahe Monch never hurts. https://www.youtube.com/watch?v=JZ6-FYAngvc

I'm sure you'll get tons of suggestions. This book often pops into my head when people ask about this.

http://www.amazon.com/Knowledge-Reigns-Supreme-Transgressions-Education/dp/907787450X

Here are some old threads you might want to skim through.

http://www.reddit.com/r/hiphopheads/comments/eojq5/help_a_teacher_expose_his_kids_to_good_hip_hop/

http://www.reddit.com/r/hiphopheads/comments/1ib8d4/help_me_design_a_hiphop_curriculum_for_my_students/

http://www.reddit.com/r/hiphopheads/comments/17rbs3/out_of_all_the_songsalbumsrappers_who_dont_have/