I've never really resonated with Rappers except with ICP with their song "Homies" (Not gonna put it on because it has a lot of expletives but its meaning of friendship resonates well.). But, recently, I found out about a couple of rappers that feel really good with both their beat and their lyrics.
One is Atmosphere. Slug (Sean) raps really well and talks about true life, like in his song "Yesterday" about him missing his deceased dad and the regret he has for leaving him in coldness.
Another is Aesop Rock. True to his alias, his raps emit great vocabulary. He raps so quickly, you only hear his true meaning by reading along with his raps. However, a lot of them feel really well crafted.
Please, share who you think are also really good rappers or hip hop singers, classic or not.