You won't be laughing when your covered wagons crash

from Aesop Rock – Daylight Lyrics on Rap Genius

Meaning

Refers to the settlers in the previous line by using the idea of covered wagons such as the ones that settlers used when moving west in early American history.

This metaphorically means that the consumers of mainstream music (the settlers) will not enjoy (won’t be laughing) when their famous rap icons (covered wagons) are not famous anymore and quit making music (crash). This happens alot in mainstream music where the top artist is shifting daily and only holds a few months of fame.

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