Why stars like johnny depp burn through their fortunes: following the money down the drain

When Michael Jackson blew through $6 million during one shopping trip in Las Vegas, an outing that turned into the biggest takeaway from a 2003 British TV documentary that painted the pop star as the consummate weirdo, it became the go-to example of why Jackson was said to be $400 million in debt when he died.
Let's see, $6 million x 365 days in a year...plus all that Neverland Ranch upkeep...
But even if he didn't have seven-figure expenses every single day, the real question was, what happened to all the money Jackson made over the course of his four-decade career? 1984's Thriller was the second best-selling album of all time when he died (it's since become No. 1). His 1991 recording contract with Sony alone was for $65 million, not including touring and the endless monetizable aspects that go hand-in-hand with the sort of game-changing music Jackson was producing at the height of his career. He spent "only" $47.5 million in 1985 on ATV Music, which included the Lennon-McCartney portfolio. Sony then bought half the rights to the ATV catalog in a 1995 merger for $95 million.
So even if he was spending like a maniac, which he apparently was ($8 million in annual travel and antiquity acquisitions alone as the 20th century became the 21st), how did Jackson end up close to half a billion dollars in the red?

The answer is utterly average.
Unpaid loans. The financial system that frequently gobbles up people much, much lower on the earning totem pole than Jackson also got to him. Wanting to maintain a certain lifestyle, he secured a $200 million loan in 2001 and continued to spend tens of millions more each year than he was making for the rest of his life. (Tens of millions also went to settle various civil claims brought against him for alleged child molestation. He was acquitted of criminal charges in 2005.)
For anyone who's ever been in the slightest bit of credit card debt knows, it's alarmingly easy to spend beyond one's means. Even if—or maybe especially if—your means are seemingly infinite.
Ironically, after his sudden death in 2009, money started pouring back into his estate (the sale of his half of the Sony/ATV catalog for $750 million helped secure a cushion for his kids' future) and Jackson's is one of the most posthumously flush afterlives around.
But while Jackson's financial troubles proved a shocking and tragic cautionary tale at the time, he's in storied company when it comes to poor money management among the celebrity set. Considering how prevalent money issues are among regular people, just add some zeroes and you've got Hollywood Economics 101: Amex Is Going to Want You to Pay That Bill One Day