I used to want to see the penitentiary way after elementary
Thought it was cool to look the judge in the face when he sentenced me

from Kendrick Lamar (Ft. GLC) – Poe Man's Dreams (His Vice) Lyrics on Rap Genius

Meaning

Kendrick used to think that doing crime was cool.

This could be a reference to Kendrick’s favorite rapper Tupac on “Dear Mama,” where he says “And who’d think in elementary? Hey! I see the penitentiary one day.” .

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