Michael Jackson was arguably the most famous singer on the planet, having sold over 100 million albums during his career. However, due to his lavish lifestyle (his “Neverland” Ranch was a fully-functioning amusement park) and legal hassles (he settled out of court molestation charges several times), the singer was $500 million in the hole the last year of his life. An attempted financial and creative comeback tour ended abruptly with his sudden overdose death in 2009, an addiction due mainly to stress and exhaustion. (Since his death, Jackson's estate has made $2 billion dollars.)