From embarking on huge spending sprees, to comletely neglecting tax bills and making dodgy investments, celebrities seem to have a knack of flushing millions of dollars down the drain. But all is never truly lost when you’re an A-lister. In this list, we’ll have a look at some of the most notable stars who have burnt through fortunes most people could only dream of, just to make it all back again.
Will Smith
Will Smith’s appearance in The Fresh Prince of Bel-Air made him a millionaire almost overnight at the age of just 22. If you give any 22-year-old that sort of money though, they’ll likely follow in Smith’s footsteps, and go on a huge spending spree, indulging in a lavish, unsustainable lifestyle.
At the height of his spending, Smith was hit with a huge $2.8 million tax bill by the Internal Revenue Service, which forced him to hand over almost all of his fortune. Following a string of successful movies, Smith built his wealth back up and is now one of the richest actors in Hollywood.
Lady Gaga
Lady Gaga built up a quick fortune following the release of her 2008 breakthrough album, The Fame, and the success of its singles, Just Dance and Pokerface. However, she managed to bankrupt herself in 2009, semi-intentionally, by throwing all of her $3 million fortune into the set design for her tour.
It was a risk that she felt she had to take, as she wanted to catch the eye of music promoter Arthur Fogel. Thankfully for Gaga, Fogel was impressed with what he saw of her live shows, and offered her, on behalf of his company Live Nation, a $40 million cheque.
Mike Tyson
Mike Tyson’s life has been full of ups and downs, with one of the highs being the extraordinary success of his boxing career earning him around $400 million. However, in a tale not unfamiliar, he had little knowledge of what to do with his money, embarking on a spending spree and living beyond his means.
When he was slapped with a string of tax bills from various different authorities, Tyson ended up $28 million in debt, with no real way of paying it all back. Over a decade and a trip to rehab later, Tyson is now debt-free, living a comfortable life that he remains fully in control of.
Meatloaf
An unsuccessful album and a host of health problems caused the singer Meatloaf to lose the wealth that he had amassed in the 1970s from hits such as Bat Out of Hell. His album Dead Ringer was a commercial flop, and shortly after its release, Meatloaf was hit with a lawsuit from his songwriter Jim Steinman.
To make things worse, he developed a cyst on his vocal cords, leaving him unable to sing. However, he managed to pick himself up, regaining strength in his voice in 2008, and heading out on tour. He also acted in a handful of movies and published a book, leaving him with a net worth of around $45 million at the time of his death in 2022.
Kim Basinger
Kim Basinger was once worth around $5.5 million, but after pulling out of a movie and being sued by the production company for a breach of contract, she found herself having to file for bankruptcy. This traumatic event led Basinger to step away from acting for three years.
Basinger was eventually persuaded to return to the movie industry by Curtis Hanson, who offered her the role of Veronica in L.A. Confidential. The movie was a huge success, winning her a Golden Globe and resurrecting her career. She has now drastically surpassed her original wealth.
Walt Disney
Walt Disney started his first film company in 1922, making short advertisements for companies. Business, although not to the scale of what he would later achieve, was going along nicely, until Disney and his partner were cheated out of a large sum of money by their distributor.
This left Disney stranded and unable to pay his bills, and by 1923 he had declared bankruptcy. He never gave up on his dream of making animated movies and short films, coming up with the idea for Mickey Mouse five years later, allowing his fairytale to finally start.
Abraham Lincoln
The path to the presidency was not always a straight one for Abraham Lincoln. Lincoln, alongside his business partner, bought a general store in Illinois in 1823 but failed to get it off the ground, with poor sales leaving the pair in serious danger of losing everything.
This danger was compounded by the death of his business partner, leaving Lincoln to pay off a large amount of debt on his own. Such were the repercussions of debt at the time, Lincoln lost everything he owned. He continued paying off debts for around 15 years, before rebuilding and moving into the White House in 1861.
Cyndi Lauper
1980s pop sensation Cyndi Lauper didn’t have it easy when she was trying to break into the music industry. Her late 70s band Blue Angel struggled to gain a great deal of momentum after releasing their one and only album. Things got worse in 1981, when the group were hit with a lawsuit from their former manager whom they had fired.
This left Lauper bankrupt and seemingly without direction. She carried on pursuing a musical career though, releasing her seminal solo album She’s So Unusual in 1983. This brought her worldwide fame, with hits such as Girls Just Want to Have Fun making her a millionaire.
Larry King
Larry King was looking down on his luck in the early 70s as he was being sued for stealing around $5000 from a former business partner. By 1978, he had lost all of his broadcasting jobs, leaving him with little choice other than to file for bankruptcy and try and rebuild his life in another industry.
However, all was not lost for Larry King, as later that year he was offered a nightly television slot by production company Mutual Broadcasting, which would see him hosting his very own chat show. The Larry King Show was a staple of American late-night television for the next 25 years.
Marvin Gaye
It was a failed relationship that almost cost Marvin Gaye his entire career. Gaye owed his ex-wife around $600,000 in 1976, which forced him to declare bankruptcy, despite the success he’d had earlier in the decade. To settle the debt, he promised to give his ex-wife 100% of the royalties from his next record.
The album was filled with songs throwing shade at his current situation, but at least Gaye had settled his debt. Gaye experienced a rejuvenation of his career and his bank balance in the 1980s, with hits such as Sexual Healing. All was looking up for Gaye at the time of his death in 1984.
Shane Filan
Former Westlife singer Shane Filan found himself in a spot of bother when the 2008 global recession hit. A few unwise investments had left him floundering in around $23 million worth of debt, with no obvious way of getting himself out of it.
He did manage to pick himself up again, working on various projects, including a solo album, after Westlife split up in 2012. Filan is now debt-free, with Westlife’s reunion tour in 2018 helping him maintain a more comfortable lifestyle.
Burt Reynolds
Burt Reynolds was a former Hollywood actor who enjoyed his first career peak in the 1970s. This stardom came with a fortune; a fortune that Reynolds didn’t hold back on spending. He bought lavish mansions, helicopters, luxury cars, and even a huge ranch in Florida.
This soon caught up on him, and in 1998, he declared bankruptcy, owing creditors around $10 million. Reynolds didn’t even have to wait a year before he made his big comeback, winning a Golden Globe at the 1998 awards ceremony for his performance in Boogie Nights.
George Foreman
When George Foreman retired from his boxing career, he probably didn’t think he’d have to come out of retirement ten years later to rescue himself from financial collapse. But come back he did, winning his next 23 fights, and reclaiming the heavyweight world championship title once again.
He then went on to associate himself with a range of small grills, which sold extremely well, making him famous for something other than boxing. He sold his shares in the company for $137 million, fully bringing himself out of his financial struggles once and for all.
Lindsay Lohan
Lindsay Lohan had made a comfortable living before she had even turned 18, appearing in films such as Parent Trap and Freaky Friday. Her career was further enhanced by the success of Mean Girls, but this early stardom was about to throw Lohan a few curveballs.
Lohan had started to earn a reputation for being difficult to work with, meaning she lost out on a few mega roles. She also had the IRS on her back, who seized her bank account in order to take the money they were owed. Lohan was on the brink of bankruptcy, but has since managed to rebuild her career and her funds.
Shia LeBeouf
Shia LeBeouf is another example of the financial and mental dangers that young, child stars can be vulnerable to if they are not looked after properly. LeBeouf started his acting career on the Disney Channel, before finding further success in movies such as Transformers and Indiana Jones.
However, LeBeouf’s mental health took a turn for the worse, and he started to behave erratically, ditching acting roles for intense live art exhibits, and making incoherent statements on red carpets. LeBeouf seems to be in a better place nowadays and has managed to build his wealth back up again after an extended financial dry spell.
J.K. Rowling
Esteemed author J.K. Rowling was going through a divorce and looking after a child as a single parent before she published the first of the Harry Potter books. This left her all but penniless, with no stable way of escaping her financial issues, as the prospect of being a published author seemed a world away.
After completing her novel, it was rejected by multiple publishing houses, before Bloomsbury Books took a punt at it. The rest is history, as the Harry Potter books and their subsequent movie series took the world by storm, turning J.K. Rowling into a billionaire.
Winona Ryder
Winona Ryder’s career was only looking up in the late 1980s/early 1990s, as she landed roles in classic movies such as Edward Scissorhands, Beetlejuice, and The Crucible. However, in 2001, she was arrested on charges of shoplifting and being in possession of illegal prescription drugs.
This tainted her image and led to her being cast out of Hollywood for some time before she eventually made a comeback a few years later. She has since appeared on the global hit show Stranger Things and is firmly back on her feet both financially and in a career sense.
Nicolas Cage
Nicolas Cage had a very obvious career peak, seemingly appearing in every other Hollywood movie over a ten-year period. This helped him to amass a huge fortune, which he tore through in a heartbeat. He bought land, yachts, ancient artefacts, and even a private island.
His excessive speeding naturally caught up with him, and as his movie roles began to dry up, the IRS came for him with a bill of $13 million for unpaid taxes. It seemed as though Hollywood had seen the last of Cage, but in recent years he has found his feet and made some high-profile appearances in movies and video games.
Sinbad
David Adkins, known to many as Sinbad, is a comedian and writer, with his most notable work including The Good Burger and Jingle All The Way. He also had his very own TV show at one point, which would suggest he wasn’t doing too bad for himself financially.
This didn’t prove to be the case forever though, as in 2011 he filed for bankruptcy, owing $11 million dollars to a couple of credit card companies, the Californian tax board and the IRS. In recent years, Sinbad has managed to find his feet again, taking a handful of acting roles, and performing stand-up comedy shows.
Stephen Baldwin
The actor Stephen Baldwin first gained fame appearing in movies such as The Usual Suspects and The Flintstones in Viva Rock Vegas. While he never joined the top table of high-profile actors, he still should have amassed a decent fortune during his time in the limelight.
However, Baldwin filed for bankruptcy in 2009, having lived beyond his means for too long, amassing around $3 million worth of debt. He made the rather brave choice of turning to Christianity, taking acting roles in mainly faith-based movies. This may not have earned him A-lister-level money, but he has pulled himself entirely out of debt.
Brett Butler
Personal struggles with addiction meant that Brett Butler’s reputation, and financial stability, soon came spiralling downward. Throughout the 90s, she had been playing the lead role in Grace Under Fire, but her on-set behaviour became untenable for the directors, and she had to be released from the role.
Butler left the limelight of Los Angeles for rehab, but ran out of money, ending up in a homeless shelter in Georgia. She eventually made it back onto her feet, returned to acting and played roles in The Walking Dead and Apple TV’s The Morning Show, helping her to recoup a lot of her lost fortune.
Robert Downey Jr.
Robert Downey Jr.’s career started to take off in the 1980s when he was still young. However, the bright lights of Hollywood seemed to take their toll, with Downey Jr. engaging heavily with substances and alcohol, as well as having a few run-ins with the law. At one stage it looked as though his career would never recover.
However, after spending time in rehab recovering from his troubles, Downey Jr. knew he had too much talent to waste. He gradually got back into the swing of acting, before landing the role of Iron Man in 2008, a role he has made his own over the last 15 years.
Martha Stewart
Martha Stewart once ran a hugely successful catering company, was the author of a handful of best-selling books, and ran her own magazine. But, businesses can often be derailed in an instant, which is exactly what happened when Stewart was arrested on suspicion of insider trading.
She was sent to prison for five months and it looked as though she’d never manage to recover her credibility. This didn’t prove to be true though, as she eventually managed to get her company churning out profits once again, this time legally, as well as finding her way onto people’s screens, presenting a TV show alongside Snoop Dogg.
Toni Braxton
Toni Braxton has sold over 70 million records and has been a famous face since the early 1990s, enjoying success with records such as Un-Break My Heart and Spanish Guitar. You’d think her early success would have set her up for life, but unfortunately, that wasn’t the case.
Excessive spending and IRS debts led to her filing for bankruptcy, not once, but twice: once in 1998 and the second time in 2010. In 2013, she finally became debt-free, and only six months later purchased a $3 million home in California. Her financial comeback was largely helped by her reality show, Braxton Family Values.
Ted Nugent
Ted Nugent’s sell-out shows and hit records in his home country of the United States initially earned him an impressive fortune, but unfortunately, he made the mistake of trusting the wrong people to look after his money. His managers at the time decided to invest his cash into multiple failed businesses.
These poor investments led Nugent to file for bankruptcy in 1980, forcing him to rush-release a string of horrific albums in order to recoup his lost finances. He has since made multiple appearances on reality television and even resorted to attempting to act to try to get himself back on his feet.
Billy Joel
Piano Man Billy Joel is one of the most successful, highest-selling musicians of all time, but thanks to an ill-willed manager, who siphoned around $30 million from him to use in dodgy business ventures and investments, he ended up having to file for bankruptcy.
Joel was unaware of what was happening with his finances, as the manager in question was Frank Weber, Joel’s brother-in-law, and the godfather to Joel’s daughter. This didn’t stop Joel from eventually taking Weber to court for a sum of around $90 million, for fraud and misappropriation of finances.
Isaac Hayes
The peak of Isaac Hayes’ music career was in the 1960s and very early ’70s. By 1975, the times when Hayes was producing top-selling soul record after top-selling soul record were behind him, and as his record sales were hitting a low, his record company’s finances were too.
Stax Records became insolvent in 1975, shutting their doors while still owing Hayes around $5 million. With over $6 million worth of debts, Hayes declared bankruptcy and had to hand over all the future royalties from his music. He did manage to make a comeback eventually, mostly by playing the voice of Chef in South Park.
Willie Nelson
Willie Nelson is widely admired and loved across the length and breadth of the USA, with records such as Stardust making him one of the country’s biggest-selling artists. This comes with a huge fortune, and a huge fortune inevitably comes with a huge tax bill. $32 million in Nelson’s case.
Nelson’s accountants had been failing to pay his taxes for years, leaving him with no other option but to file for bankruptcy. This led to Nelson appearing in Taco Bell commercials, and even releasing an album specifically for the IRS in order to try and pay back the debt. Nelson’s reputation came through the battering, and he eventually managed to become financially stable again.
Mick Fleetwood
Mick Fleetwood was the drummer and glue of his former band Fleetwood Mac, who are best known for their 1970s album, Rumours. At one point, Fleetwood Mac was one of the biggest bands in the world, with their music still selling incredibly well to this very day.
This didn’t stop Fleetwood from burning a rather gaping hole in his once huge pockets, through excessive use of a certain white powder. Fleetwood filed for bankruptcy in 1991 and didn’t manage to get back on his feet for another decade. The historic success of his band and occasional stage appearances have meant that Mick Fleetwood is once again thriving.
Jerry Lee Lewis
Jerry Lee Lewis was one of the emerging stars of rock ‘n’ roll in the 1950s, and is still best known for his hit, Great Balls of Fire today. 22-year-old Lewis’ success was at its peak when news got out that he had married his 13-year-old second cousin, a couple of months before his divorce from his previous wife had been finalized.
Lewis’ credibility was rightly destroyed, and with his rock ‘n’ roll career in the mud, there was only one direction he could go: country music. This helped him recoup some of his money, along with the royalties from Great Balls of Fire propping him up for years to come.
Diego Maradona
Diego Maradona is widely considered to be one of the top three greatest footballers of all time, hailed as a god in his home nation of Argentina and the city of Naples, Italy for his contributions to the sport. However, geniuses are always vulnerable to dangerous vices, which is exactly the trap Diego fell into.
Maradona’s wild lifestyle and lax attitude to paying taxes left him with a huge $53 million bill from the Italian tax authorities. As a result, Maradona declared bankruptcy but somehow managed to keep hold of his huge properties and jewellery collection. His family are still at war with the legal authorities to try and keep hold of his assets.
Evander Holyfield
Former heavyweight world champion Evander Holyfield amassed an incredible $460 million fortune throughout his long boxing career, bolstered by his huge, controversial, fight against Mike Tyson. This fortune wasn’t to last, mainly because of Holyfield’s turbulent relationships.
The former boxer has 12 children with three different ex-wives, with divorce payments and child support payments putting a severe dent in his once-large fortune. The IRS also came for Holyfield to collect missed tax payments. He has since got back on his feet, reportedly making around $1.2 million a year from personal appearances.
Chris Eubank
Former British boxing world champion Chris Eubank joins Evander Holyfield and Mike Tyson in the once-bankrupt boxers club, having experienced financial difficulties after his retirement from the sport. His excessive mid-career spending carried on after he was no longer bringing in big-fight money.
This was compounded by his divorce and a $1.6 million tax bill he received from HMRC. This didn’t dampen the spring in Eubank’s eccentric step though, as he claims his financial struggles to be important life lessons. Various television appearances and boxing punditry have enabled Eubank to recoup some of the fortune he once lost.
P.T. Barnum
P.T. Barnum, inventor of horoscopes and the subject of the movie The Greatest Showman had a rocky journey to the top after the building he had bought and upgraded burned down… five times. This plunged Barnum into the depths of bankruptcy, meaning he had to find another way to make it.
Barnum went on to conceive the idea that eventually made him one of the biggest names in showbiz, the three-ring circus. Barnum’s moving circus was the first of its kind, and at 64 years of age, he had finally recovered his lost finances, raking in a fortune.
Elton John
Elton John’s discography speaks for itself. It’s packed with some of the greatest songs ever written, with his and Bernie Taupin’s hits regularly topping the charts in the ’60s, ’70s, and ’80s. You’d have thought this would have set him up for life, but Elton’s lavish lifestyle got in the way.
In 2002, he filed for bankruptcy after the debts on his multiple properties around the world became out of control. To get himself out of this hole, he agreed to play 75 shows over three years in Las Vegas. He released a handful of successful songs and played more huge shows, including a triumphant Glastonbury set in 2023. He is now worth a reported $450 million.
MC Hammer
U Can’t Touch This singer MC Hammer grew up poor, making money from gathering stray baseballs outside the Oakland stadium. When he finally made it big, he had a lack of real financial advice around him, and he blew a lot of his money buying luxury items and giving cash away to family and friends.
By 1996, he was $13 million in debt and filing for bankruptcy. He has since worked his way back to a comfortable financial state, playing a selection of big shows, and claiming the royalties from his big 1980s hits. He may not be worth quite as much as he used to be, but he’s no longer in financial ruin.
Stan Lee
Before he created the multi-billion dollar Marvel Universe, Stan Lee fronted a media company that filed for bankruptcy in 2000. Lee could well have lost all of his creations that he had spent years conceiving of until that point, had he not thought of an effective loophole to jump through.
Lee assigned all of his famous comic book characters to a new company called POW! Entertainment, which meant that he retained the rights to them. The Marvel Cinematic Universe was later founded, which made Stan Lee a very rich man up until his death in 2018.
Francis Ford Coppola
Even after making the movie that many would consider the greatest of all time in The Godfather, director Francis Ford Coppola went on to file for bankruptcy three times in a nine-year span. This was mainly caused by Coppola owing people money, debts he had expected to pay off through various projects, which eventually flopped.
Coppola eventually managed to settle his debts and carried on making movies, many of which allowed him to regain financial stability after a turbulent period in his life. He also got into winemaking, purchasing a large vineyard in Napa County, California.
50 Cent
50 Cent was once worth a staggering $155 million, but filed for bankruptcy in 2015, following a string of bad financial decisions and mishaps in his personal life. 50 Cent’s lavish lifestyle saw him burn through the lion’s share of his wealth, but that wasn’t the main reason for his downfall.
A major tax bill, and a lawsuit against 50 Cent from Rick Ross’ ex-girlfriend after 50 Cent had allegedly published intimate videos of her online, led to a mountain of debt at the rapper’s door. He eventually managed to pay it all off in February 2023 and has since been able to begin growing his wealth once again.
David James
Former Liverpool and England goalkeeper David James earned around $25 million during his football career, through his salaries and endorsement deals. However, less than a year after he called time on his playing days, he filed for bankruptcy, auctioning off his memorabilia and trophies to pay off his debts.
The trouble stemmed from some ill-advised investments, as well as his divorce from his wife. In the years since filing for bankruptcy, James has regained some of his lost fortune by working as a TV pundit and fulfilling coaching roles for various different clubs in the UK and abroad.
