Back through the system with the riff-raff again

from Jay Z – 99 Problems Lyrics on Rap Genius

Meaning

The worst part about prison is…the people!

Jay has experienced prison before, when arrested for an assault charge stemming from an alleged stabbing of Lance Rivera in a nightclub. Jay was held for a number of days, just after the release of one of his most successful albums, and was eventually given probation.

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