7. Michael Jackson
During his final years, more was reported about Jackson's bankruptcy and those pesky child molestation rumours than his actual music. But I suppose nothing changes after death. His problems began in the mid '90s with the first of many child abuse allegations surfacing. His music career slowed down from what it had been the '80s and the King of Pop began borrowing money left and right. He was also overspending by about $30 million each year. Before he passed away, he was deeply in debt (about $500 million). Even after death, the Jackson's estate may not be out of the woods. The IRS believes that his estate was undervalued and owes $700 million more in taxes. But on the bright side (or depressing, since he passed away), the estate has been raking in profits since his death due to the release of This Is It, the nostalgic purchases of his music and the lack of outgoing money.