When it comes to money management, it can get real out here—even for the rich and famous.

With the release of ESPN’s newest 30 for 30 documentary, Broke, it dawned on us that there’s been way too many hip-hop heads who blew away mountains of big bucks over the years.

Check out this list we threw together of the most notable hip-hop personalitie

s to file for bankruptcy. Here’s to hoping that they learned a valuable lesson.

Peep the gallery (starting below) to see our picks of people in the industry you wouldn’t want handling your guap:

MC Hammer

A reported “spending spree,” including a multimillion dollar mansion and half a million dollar payroll, resulted in Hammer’s 1996 bankruptcy. He definitely gave a new meaning to his infamous lyric, “Uh Oh!”