I was talking with my mate the other day about how crazy it is that some of the richest celebs can end up flat broke. You might think millions would put you on the right side of life, wouldn’t you? But golly, some of these stories are certifiable bonkers.
Here’s a look at the most shocking celebrity financial meltdowns that’ll make you grateful for your savings account, no matter how modest it might be.
1. Mike Tyson—From £300 Million to Absolute Zero
O.K., let’s begin with Iron Mike. This ex-boxer made an estimated £300 million through boxing but had lost it all by 2003. I mean, how do you spend that much? Well, Tyson found a way. He purchased white Bengal tigers (yes, real tigers!), shelled out millions on cars he hardly drove and threw parties that cost more than most people’s homes. A combination of legal fees and debts owed to the I.R.S. pushed him over the edge and into bankruptcy in 2003.
What gets me about Tyson’s story is how he’s turned it around. The bloke went from being completely broke to starring in films and doing comedy shows. Fair play to him for bouncing back.
2. 50 Cent—The Millionaire Who Wasn’t
Curtis Jackson, more famously recognised as 50 Cent, is a prime example of how lawsuits can bury you without a shadow of a doubt. He filed for Chapter 11 bankruptcy in 2015, listing debts of more than £22 million. The rapper was also facing £36 million in debts, mainly as a result of lawsuits.
The irony? This was the dude who rapped about getting rich or dying trying. Sometimes life has a wicked sense of humour, doesn’t it?
3. MC Hammer—Can’t Touch This (Money)
Stanley Burrell, who went by the name MC Hammer, was earning £30 million a year in his heyday. But his expenditures were simply crazy. The man had a 40-room mansion and more than 200 employees, and he bought everything in sight. And by 1996, he was flat broke, forced into bankruptcy with debts of £13 million.
I remember seeing his music videos as a kid and imagining that he had it all together. Well, it shows you can’t judge a book by its cover, innit?
4. Nicolas Cage—National Treasure Turned National Disaster
This one gets me really going, as Cage was making crazy money and squandering it on the weirdest things imaginable. We’re talking about castles, pyramids, islands, and rare comic books. His portfolio of properties alone was insane: houses from New Orleans to the Bahamas.
Then the taxman came knocking, and suddenly Cage was on the hook for millions. He’s been working nonstop since, accepting nearly every film role that came his way just to pay off his debts. A bit sad really, considering he’s actually a brilliant actor when he wants to be.
5. Michael Jackson—The King Who Lost His Crown
The King of Pop’s financial troubles were absolutely heartbreaking. Jackson remained in debilitating debt when he died, despite earning hundreds of millions over his career. His expenses related to Neverland Ranch, his growing legal problems, and his extravagant lifestyle left him with a reported debt of a massive £400 million.
Jackson’s story hits different because his music was such a massive part of growing up. Seeing someone that talented struggle financially just seems wrong.
6. Toni Braxton—Unbreaking Her Financial Heart
Braxton filed for bankruptcy, not once, but twice; reportedly once in 1998, because she was getting low royalties from her record label, and the second time in 2010 after she cancelled her Vegas show, citing illness. Her story illustrates how even successful artists can get absolutely stitched up by record deals.
The music business can be downright ruthless. Artists are the ones making the content that generates millions of dollars in revenue, but often see very little of it themselves.
7. Gary Busey—A Hollywood Cautionary Tale
Busey’s case is a perfect example of how quickly things can go tits up in Hollywood. One moment you’re appearing in big-screen movies, the next you’re forced to file for Chapter 7 bankruptcy. His story is proof that even successful actors are not immune to financial ruin.
8. Kim Basinger – Beauty and the Bankruptcy Beast
The Oscar winner’s money problems were caused by a disastrous business venture and a luxurious lifestyle. She purchased an entire town in Georgia for £15 million and thought it was going to be a genius investment. Spoiler alert: it wasn’t.
9. Wayne Newton—Mr. Las Vegas Goes Skint
Newton, known as Mr. Las Vegas, filed for bankruptcy despite decades of successful performances. His case is an example of how even steady earners can suffer ruin if they are careless with their spending and investments.
10. Cyndi Lauper – Time After Time in Debt
Prior to her chart-topping success, Lauper once filed for bankruptcy in the 1980s amid a dodgy record deal with a prior band. Her story is really quite amazing in that she was able to reinvent herself and become an international superstar.
The Pattern Behind the Madness
Looking at these top 10 celebrities who lost everything, there are some common themes that absolutely fascinate me. The vast majority of these stars succumbed to the same pitfalls: over-the-top spending, disastrous financial alliances, and no planning for the future.
What flabbergasts me is how many of them relied on financial advisors who either stole from them or dispensed horrendous counsel. It’s the equivalent of having a stellar career in football and letting your mate’s cousin take care of your transfers; it’s never going to end well.
In my opinion, these stories serve as proper warnings. Fame and fortune can vanish more quickly than you can say “bankruptcy court.” Those celebrities who successfully bounce back are generally the ones who actually figure out where they went wrong and start treating money with the respect it deserves.
These stories are a reminder that no matter whether you’re making minimum wage or millions from a film, financial literacy matters. The concepts are identical: spend less than you earn, put aside a rainy day fund, and don’t believe anyone who purports they can make you richer.
The good news? And many of these stars have since moved on with their lives and careers. Their stories show that going bankrupt is not the end of the world; sometimes it’s just a very expensive lesson in money management.
