15 Riches to Rags Stories of Entertainers Who Lost Millions

Fame and fortune can take a lifetime to achieve but often only mere seconds to destroy. There are so many celebrity success stories that are heartwarming. But there are also plenty of nightmare stories where successful celebrities seemingly lost it all in the blink of an eye.

Happiness is not the only fleeting thing because wealth can disappear just as fast. Let’s take a quick look at famous people who were rich and then lost it all.

Michael Jackson

Michael Jackson
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Although Jackson was making $100 million a year at one point, he was deep in debt when he passed away. He was overspending on real estate such as millions on the Neverland Ranch, funding art projects and settling legal battles including the child molestation charges in 2005. 

Meat Loaf

Meat Loaf the singer
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Meatloaf made his musical debut in 1977 with his hit, Bat Out of Hell. However, a variety of legal troubles and battles with his recording company led to his ultimate downfall in the early 1980s, just a few years after his debut.

At one time, there were over $100 million worth of lawsuits filed against him. Surprisingly enough, after he filed bankruptcy, he managed to make a comeback and substantially regained much of his wealth before his death in 2022. 

Sinbad

Sinbad
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David Adkins, known as Sinbad on the comedy stage, was one of the most successful comedians of the 1990s. He also had a variety of television shows, including his own self-proclaimed “The Sinbad Show”.

Though he earned millions of dollars from his ventures, he actually had to file bankruptcy twice, once in 2009 and a second time in 2011. He was in debt of nearly $11 million which he owed to the government. However, Sinbad seems to have bounced back, with a current net worth of roughly $4 million.

Dennis Rodman

Dennis Rodman
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Dennis Rodman is perhaps one of the most talented NBA basketball players of all time, having spent 12 years in the sport, earning over $27 million during that time. However, at this time, Dennis Rodman net worth stands at just over $500,000.

Bad financial investing is what is generally to blame here. He hired a very shady financial advisor, Peggy Fulford, who ended up spending ten years in prison due to fraud charges, mainly due to scamming Dennis Rodman and other victims. 

Toni Braxton

Toni Braxton
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Toni Braxton is a Grammy Award winner, and she had assets worth over $10 million, as well as other financial holdings. But simultaneously, in 2010, she also filed for bankruptcy due to owing over $50 million. She then filed for bankruptcy again in 2013, and at one point even had a lien filed against her by the IRS.  

The only thing that saved Braxton from being millions of dollars in debt was her new reality TV show, Braxton Family Values, which managed to boost her net worth up to $10 million again, which it sits at today.

Willie Nelson

Willie Nelson
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Who doesn’t love Willie Nelson? The IRS, that’s who. At one point, in 1990, Willie Nelson owed over $32 million to the IRS in back taxes, at which time the IRS seized most of his properties and assets.

Even after his assets were seized, he still owed over $16.7 million in debt. Willie Nelson is a great example of a riches to rags to riches story, as he managed to bounce back, and now features a net worth of over $25 million.

Nicolas Cage

Nicolas Cage
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Thanks to a few dozen hit feature films, Nicolas Cage once had a net worth of $150 million. However, Nicolas Cage also engaged in relentless spending, and seemingly also did not pay his taxes. In 2010, Nicolas Cage had amassed a tax bill of $13.3 million to the IRS. By 2012, he had cut this debt in half, and now, in 2023, he has a net worth of $25 million. However, $25 million is still a very long way away from the $150 million net worth he once had.

Johnny Depp

Johnny Depp
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Did you know that Johnny Depp earned over $20 million for every single one of the Pirates of the Caribbean films he did? He was even named the most overpaid actor in Hollywood in both 2015 and 2016. However, engaging in practices such as spending $30,000 on wine per month or paying $3 million to shoot the ashes of journalist Hunter S. Thompson from a cannon, took its toll on Johnny Depp’s net worth. Although he still has a net worth of well over $100 million, he once had a net worth of almost $1 billion.

Shia LaBeouf

Shia LaBeouf
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Shia LaBeouf may have a net worth of well over $25 million at this time, but it once was many times that. The star of various popular movies such as Transformers and much more, earned over $20 million from the Transformers movies alone, and he’s also been in dozens of other feature films. However, it appears as though he suffered a severe mental breakdown as he began exhibiting erratic behavior, which led to his ultimate downfall.

Mike Tyson

Mike Tyson
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Mike Tyson now only has a fraction of his wealth, as he has a reported net worth of just $3 million, whereas he used to have a net worth of over $300 million in his prime. This fame and fortune all came from his illustrious boxing career, but he then struggled with many legal and personal issues which led to a three-year prison sentence.  His most notable moment is when he bit off the ear of Evander Holyfield in 1997, and then filed for bankruptcy just shortly after.

MC Hammer

MC Hammer
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MC Hammer created what is arguably one of the most iconic and memorable rap songs of all time, and he’s also known for his super eccentric hammer pants. In 1991, he was reported as being worth well over $33 million, but he spent many times that on frivolous items, such as his own personal jet. In 1996, MC Hammer filed for bankruptcy and continued to pay off these debts over the next 20 years. At this time, MC Hammer is worth just $2 million.

Lindsay Lohan

Lindsay Lohan
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Lindsay Lohan made over $28 million from movies alone, and was worth even more. However, at this time, her net worth is just $800,000, which is mainly thanks to her bad habits and overspending.

Though she has been a recording artist, model, and actress, she now has trouble finding work due to her poor behavior and even worse reputation.

Gary Busey

Gary Busey
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For an actor who has been in the business for over 5 decades, having a current net worth of just $500,000 is abysmal. Gary Busey even had to file for bankruptcy in 2012, due to being over $500,000 in debt. It looks like starring in Walker, Texas Ranger, didn’t do Busey any good as far as preparing himself to fight the law is concerned! 

Natasha Lyonne

Natasha Lyonne
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Natasha Lyonne is knowns for her role in “American Pie” and “Slums of “Beverly Hills.” Shortly after, things went downhill for Lyonne. She became addicted to drugs and homeless. She didn’t think she would survive so that fact that she has returned to Hollywood and become an actress in demand is extraordinary. She returned to acting and landed a role in the hit series “Orange is the New Black” for which she received a Screen Actors Guild Award. 

TLC (T-Boz and Chilli)

The band TLC with Lisa Left Eye Lopes in the center
Lisa Left Eye Lopes (center) with the band TLC: Deposit photos

 

After selling 65 million albums worldwide, each member earned only $300,000 each after paying taxes, fees to the recording studio and the record company’s cut. T-Boz filed for bankruptcy in 2011 with over $1 million in debt. 

 

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Jack Black
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Salma Hayek
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