Suge Knight
Suge Knight was the CEO of one of the most successful hip-hop labels in the 1990s. With dozens of hits by 2 Pac, Snoop and Dr. Dre, Knight should have been wealthy throughout his lifetime. But in 2006 he filed bankruptcy with $11 in his bank account. The entire Death Row catalogue, which is likely worth over $100 million, sold for $24 million.