If you’ve never heard of famed “Gonzo” journalist Hunter S. Thompson you’re probably not alone. He was always more of a cult figure than a big-time celebrity, even if he was the author of such seminal books as Hell’s Angels and Fear and Loathing in Las Vegas. However, lots of actual big-time celebrities have heard of “The Good Doctor,” as Hunter styled himself and were huge fans of his. In fact, Johnny Depp, who played Thompson in the movie version of Fear and Loathing, was such a fan of his fellow Kentucky Colonel that when Thompson died, Depp shelled out a cool $3 million to shoot Thompson’s ashes out of a giant cannon, in accordance with the writer’s last wishes.
All of this brings me to the point of today’s exercise: regardless of whether you think spending $3 million on a weird dying wish is a good idea or not, the very rich are very different from you and me and can do such things on a whim simply because they want to. Well, that's to say they can do such things for no good reason at all until they do them so many times they end up just like your average Joe -- broke. Depp himself is teetering on the edge of bankruptcy as you read this precisely because of expensive stunts, overzealous purchases, and an ugly little divorce to Amber Heard. He’s not quite there yet -- the man was once worth almost $400 million after all, but plenty of stars have gone straight over that edge into total insolvency. Here are 15 celebrities you may not have realized went bankrupt.
15 Sinbad - Owed $11M
Everybody loves Sinbad -- am I right? Well, maybe not anymore, but back in the day, he was one of the biggest (quite literally) funny men out there. If you’ve ever seen Jingle All the Way, then you know what a talent the man is. Alright, alright -- I’m joking about that particular movie, but seriously, Sinbad was a big enough star in enough different vehicles to somehow have to file for bankruptcy to the tune of $11 million. You have to make an awful lot of money to owe that much money -- that’s for damn sure. He first filed in 2009 and then again in 2013. He told Oprah in an interview, "I didn't buy Bentleys. I didn't live large. I invested in me. I invested in a lot of other people. I would not change it; I would not go back." OK, that’s great Sinbad, but you might want to rethink that statement -- you owe $11 million, guy!
14 Warren Sapp - Stop Buying Air Jordans!
He might have been an absolute beast on the field, but his personal life has been anything but easy. The NFL Hall of Famer has had a rough couple of years recently. Not only did he lose his high profile job as an analyst at the NFL Network -- that’s what happens when you’re caught looking for h--kers at the Super Bowl -- but he had to declare bankruptcy as well. I wonder if he’s upset that he lost his $540,000 a year TV gig? It turns out good old Warren, formerly known as “QBK” (Quarterback Killer) in his playing days, is also something of a financial killer, mostly based on bad purchases. In 2012, he owed $6.7 million to creditors. He had “assets” of $6.45 million. Unfortunately, a whole bunch of those assets was pair after pair of Air Jordans and tiger-skin rugs. Hmm, methinks Warren might have needed a little investment advice somewhere along the way.
13 Joe Francis - Girls Gone Wild? Really?
When you make your living being a total sleazeball, chances are that your choices are going to come back to haunt you eventually. That’s exactly what happened to Joe Francis, who, you may remember, was once the king of the world. Or at least he was the king of the softcore, totally ridiculous Girls Gone Wild empire. It’s amazing to me that this thing was as popular as it was, but Francis found the perfect mix of hedonism and exuberance (on the part of his “subjects”) to make money with on late-night TV. Unfortunately for him, and fortunately for all of us who were sick of his antics, he was also found to be filming underage girls and avoiding his taxes. He owed the IRS millions upon millions when he filed for bankruptcy in 2013. He also went to jail for a while because of his dealings with the aforementioned underage stars of his videos.
12 50 Cent - Richest Broke Man in Hollywood
Well, he got rich and he didn’t die trying, but 50 Cent wasn’t able to hold on to his fortune for very long. It was only 2015 when the big-time rap superstar was reportedly worth over $150 million. But that all changed pretty quickly for him. First, he ran into a bunch of bad investments. Sources don’t say quite what all those bad investments were, but rappers, like star athletes, tend to have large 'possies' with even larger wants. I’m not saying that was 50’s deal, but you never know. Then he had to settle a huge lawsuit about a leaked sex tape (I didn’t know anyone sued over those anymore!), and voila! Bankruptcy. Unlike some stars on this list, 50 Cent actually had a plan to pay off his debt, which was anywhere from $10 to $50 million and supposedly has done, so he is now out of bankruptcy (although still paying off debt).
11 MC Hammer - You Can't Outrun the IRS
I know, I know. It’s hard to feel bad for a guy who wore genie pants -- for the guy who started the whole genie pants fad, in fact -- but the fact of the matter is that good old MC Hammer had a really rough go for a while. The man most responsible for one of the dumbest looks in modern music history was also responsible for the mega-hit “U Can’t Touch This" way back in 1990. That song was everywhere. In fact, now that I think of it, it kind of still is. Anyway, Hammer had a string of hits, including the monster smash “Too Legit to Quit.” Apart from the fact that neither you, I, nor Hammer himself ever actually considered him to really be all that legit, the money gods were already closing in on him. When I say "money gods," I mean, of course, the IRS, which in the late nineties declared that Hammer owed them about $9 million in back taxes. Hammer declared bankruptcy basically immediately.
10 Larry King - Grand Larceny?
If you’ve ever seen Larry King on late-night TV shilling that Omega XL joint pain stuff, then you might think the masterful radio and TV personality with the eponymous show was hurting for money. Well, that’s certainly not the case now, as good old Larry was worth a reported $150 million in 2015, but he actually did have to declare bankruptcy some years back -- 1978 to be precise. Apparently, Larry had over $350,000 in debt back then. He was working at the time as a radio host in Miami and was even publicly accused by a “business partner” of grand larceny. Now, I don’t know what “business” a radio personality in Miami was in, but the whole situation sure didn’t help Larry much. At least not at the time, anyway. Later that same year, though, he was offered the gig that he held onto forever, earning him back every penny of that $350,000 plus just a little bit more in interest.
9 Mark Twain
Of course, you’ve heard of Mark Twain. Everybody has heard of Mark Twain. America’s most famous original novelist, the man who wrote The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn, may not be someone you think about much these days (most of us probably haven’t thought of him much since high school), but he was once the most famous man in America. I’m talking easily -- he was bigger than the president and richer, too. In fact, he actually owned the publishing company that released the best-selling memoirs of then-president Ulysses S. Grant, a memoir that made everyone involved millions of dollars. But by about 1880, the great author had lost boatloads of money investing in a newspaper typesetting machine that failed miserably, and his publishing house was floundering. By the time a depression hit in the 1890s, Twain was well and truly screwed and had to declare bankruptcy at the ripe old age of 60 -- not a great way to finish one of the most famous entertainment careers in American history.
8 Kim Basinger - Thanks Alec
There was once upon a time when Kim Basinger was considered one of the sexiest and hottest leading ladies in Hollywood. The star of such steamy hits as 9 ½ Weeks, L.A. Confidential, as well as the first Batman, was an “It” girl for a while, even more so when she and Alec Baldwin tied the knot. Perhaps that’s why she tried to get out of her contract to star in the sexy yet oh-so-creepy artsy flick Boxing Helena. Whatever her motives, they steered her wrong. Main Line Pictures, the makers of the film, sued her for $7 million in 1993. She eventually had to pay off $3.8 million of that lawsuit and was forced to declare bankruptcy the same year. To make matters even worse for our girl Kim, she also had to face tremendous public scrutiny when she and Baldwin underwent a very nasty divorce in 2003.
7 Lady Gaga - After Her First Album
OK, just to set the record straight, Mother Monster is no longer bankrupt -- not even close, weighing in with a net worth of around $200 million in 2015. But there was a time not so long ago when she quite legitimately was, right before her Monsters Ball Tour in 2009, in fact. What happened was that Gaga, who was already a huge star making plenty of bank had about $3 million to her name in immediate, available cash. She wanted a cool stage for her show -- I mean, a really cool stage. So she took her $3 million and bought a stage. Then she went bankrupt. While she was on tour. According to the Lady herself, her Dad even said to her, “I don't understand. 'Bad Romance' is out. You are all over the radio. Everyone is talking about you and you don't have a pot to p*ss in.” However, she also says she knew what she was doing all along. Her plan was to get Live Nation’s attention and score a big pay day. It worked when they wrote her a check for the paltry sum of $40 million. So perhaps, burning your last couple million on a stage show and declaring bankruptcy is the way to go.
6 Gary Coleman - Don't Trust Mom And Pops!
Who doesn’t love a little bit of Different Strokes in syndication every now and then? Even if you didn’t grow up with the '70s sitcom that made pint-sized actor Gary Coleman an international superstar, you surely know of his signature catchphrase “Whatcha talkin ‘bout, Willis?” The show made Coleman, who suffered from poor health later in life and died in 2010, was such a huge star that he was making $46,000 per episode. That was in the ‘70s -- it was big cash back then. But by 1999, he had to file for bankruptcy, saying he was almost a million dollars in debt. What was most unfortunate for Coleman was that he had to name his parents as the responsible parties, saying that they dipped into his trust funds until there was nothing left. To which I can only say, “Whatcha talking ‘bout Mom & Dad?!!?”
5 Isaac Hayes - The Guy Who Sang Shaft
Another star who made it super-big in the ‘70s was all-time great soul singer Isaac Hayes. He’s another one you might not remember by name, but you've definitely heard his biggest hit “Shaft” more times than you know. I mean, “Shaft” even won an Oscar for Best Song (for the movie by the same name, of course). In addition, Hayes was the songwriter for “Soul Man,” one of the most recognizable hits of the 20th century. He was also terrible with money. He mismanaged his own record label, bought everything in sight, and trusted shady advisors all to the tune of a $6 million debt in 1976 and a formal declaration of bankruptcy. At least Hayes figured out his problem. He told Ebony magazine, “I put too much trust in people. I trusted people to take care of business, and I didn’t question them. Being a creative person, I didn’t like to get bogged down in a lot of administrative things. Rather, I hired people who were supposed to be top-notch.”
4 Burt Reynolds - Stupid Alimony...
Poor Burt Reynolds. He seems like such a cool dude, best known for his action roles in ‘70s and ‘80s flicks like Smokey and the Bandit and Sharky’s Machine (which is so awesomely ‘70s, even if it was made in 1981, that you have to find it now on the streaming service of your choice). He was also married to Loni Anderson, who was about as prototypically a hot starlet of her time as you could possibly get. But… Burt and Loni didn’t last. Not forever at least -- by 1996, Reynolds, who by then was sort of morphing into an elder statesman of “cool” (check out his performance in Boogie Nights if you don’t believe me) -- was divorced from Anderson, paying massive alimony and had also lost a ton of money in a failed Florida restaurant chain. He had to declare bankruptcy and even had foreclosure proceedings begin on his beloved mansion, Valhalla. But Burt is still kicking, kept the house, and is even worth about $5 million these days. Bankruptcy must have been good for him.
3 Toni Braxton - Don't Trust The Record Labels, Toni!
She was an R & B superstar of the 1990s, one of the biggest names in a revival that spawned the likes of Beyoncé, among others. She was considered a peer to Whitney Houston. She had almost 30 million units in album sales for her first three albums, two number one hits, six Grammys, and no money. That’s right, superstar singer Toni Braxton was used badly by record companies and agents, accruing less than $2,000 in royalties on her very first recording contract and ending up perpetually in debt to her record company. She also had a thing for expensive home furnishings, never a cheap way to go. She was forced to file for bankruptcy in 1998. Things seemed to take a turn for the better for Toni in the mid-2000s but then she became ill, had to cancel a Vegas residency, and declared bankruptcy again. She finally became solvent (hopefully for good) in 2013.
2 Meat Loaf - Spent It On The Gravy
It’s not the biggest bankruptcy filing a celebrity has ever gone through, but it’s not the smallest either. Actually, given that he declared for bankruptcy not once but twice in the ‘80s, perhaps Meat Loaf was just trying to set the record for bankruptcy filing at the time. The singer, who is most famous for the rock anthems “Paradise by the Dashboard Light” and the all-time (and widely misunderstood) arena rock anthem “I’d Do Anything for Love (But I Won’t Do That),” was in debt for about $1.5 million the first time he lost everything. That’s what I don’t get. His songs were huge hits. He made a sh*t-ton of money. He couldn’t possibly have had the imagination to spend everything himself on crazy stuff, could he have? I mean, this is Meatloaf, not Johnny Depp. He literally is a meat & potatoes kind of rock star. Who knows? Maybe he spent it all on gravy…
1 Mike Tyson - $26M in Debt...
$26,000,000, give or take a few million. That’s the staggering number we have to work with when we consider Mike Tyson’s debt in 2003. I don’t think I could spend $26 million if I wanted to. However, if there’s anyone out there who wants to give me the opportunity, I’ll gladly give it a shot. But anyway, I digress. The most astounding thing about Tyson’s bankruptcy filing is that he had supposedly made over $350 million in his career. I can’t really wrap my head around the $26 mil number, so $350m is kind of completely beyond my ken. What I do understand, though, is that Iron Mike spent a lot of cash on a lot of crazy stuff. Most shocking (and awesome) was the $10,000 he owed in back fees for “care of his tigers.” Yup, you read that right -- Tyson had tigers and he wasn’t paying the bills to keep the tigers happy. I don’t know about you, but if I had tigers living with me, I would do everything possible to keep them happy.
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