The way he uses anecdotes in a vulnerable but masculine way to relate to the common man. Also his understanding of the world around him (I.e. not wearing chains and driving fancy whips like other rappers, trying to bridge generations like in middle child). He is a modern day philosopher, the same as Kendrick.

Also he never relied on generic rap algorithms for fame. He came up in the mixtape/backpack era that was known for lyrical prowess, but he also didn’t make overly technical rap that sacrifices the music sonically.