MC Hammer

MC Hammer was the first rapper to earn millions as an artist during the late 1980s. However, his $500,000 monthly payroll and spending habits led to a $30 million loss.

A.R. Shaw

A.R. Shaw is an author and journalist who documents music, politics, and entertainment. He has covered The Obama White House, the summer Olympics in London, and currently serves as Lifestyle Editor for Rolling Out magazine. Follow his journey on Twitter @arshaw and Instagram @arshaw23.