I should have known

from Childish Gambino (Ft. Danielle Haim) – Won't Stop Lyrics on Rap Genius

Meaning

A reference to another song on the mixtape Shoulda Known. The theme in that song also rings throughout this one as well. Childish seeks validation for his actions and hopes that what he’s done can make his whole family proud (which, according to his father, he has successfully done). He still at times feels guilty (which is why he repeats that he should have known)

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