50 Cent filing for chapter 11 bankruptcy this morning was one of the most unexpected turn of events of the year. Even with his $5 million payment to Rick Ross' baby mama last week, 50 seemed to have an unlimited supply of cash between his rap career winnings, minority stake in Vitamin Water (sold to Coca-Cola for $4.1 billion in 2007), and current spread of business enterprises. The May 2015 bankruptcy of his SMS Promotions boxing company perhaps should have been the canary in the coal mine.

The lesson here is that things are not always as they seem. Even for someone as rich as 50 Cent, a couple bad investments paired with a lavish lifestyle can obliterate millions of dollars overnight. But keep your chin up, 50, you are not the first rapper to file for bankruptcy. Today we revisit the handful of hip-hop figures who have been forced to do the same.

This list does not include the many rappers who've owed back taxes to Uncle Sam.