2. Michael Jackson
Michael Jackson was one of the biggest pop stars in music, worldwide for many years. He had a very different lifestyle which changed as years progressed. He did a lot of cosmetic surgeries, had an out of controls hopping habit and was under the influence of drugs. His life gradually started falling apart. He had been married twice but both of his marriages were short-lived and unhappy. In 2003, he was arrested after a criminal investigation followed by the documentary film ‘Living with Michael Jackson’. Due to the numerous court cases, he lost his fortune and became bankrupt. He burned through most of his money and fame by the time he died in 2009.