Top 3 hip-hop Tiny Desk Concerts to me. I don't listen to it very often, because it makes me too sad. His performance of 2009 absolutely kills me, knowing he passed just a few months later.
I honestly didn't really follow him until after he passed. His early frat-rap stuff that got got him attention initially wasn't really to my taste and I never came back to him until Circles came out, a couple years after his death.