5.Tom Petty
Formerly the lead vocalist and guitarist of the rock band Tom Petty and the Heartbreakers, Tom Petty was also a member of another supergroup, the Travelling Wilburys. He recorded a number of singles that made it big back in the 1970s and 1980s. Petty was pretty prolific and was able to sell 80 million copies in his lifetime.
One attribute this former guitarist had was being shrewd. He is perhaps the only one on the list that wanted to declare bankruptcy not because he was penniless but as a way to get out of a contract. In 1979, he expressed his intent to file for bankruptcy because he felt that his contract with his record label then was oppressive and used creative accounting so that he would not earn that much anymore. The attorneys of the opposing side tried to convince him, but he remained rock solid, prompting a readjustment of his terms so that his action would not set a precedent for other artists.