Julia Stiles: Obscurity

After starring in 10 Things I Hate About You and Save The Last Dance, Julia Stiles hit a financial bump in the road. While she didn't invest her money recklessly or spend too much on realty and luxury items, critics trashed her biggest movies and her TV career floundered – which meant a smaller stream of money pouring in. Unable to meet mortgage and car payments, the actress was near a financial crisis until she was cast in the Jason Bourne film series. Unfortunately, her role was killed off in the franchise after a 14-year run.

Brendan Fraser  - Steep Child Support Payments Made Him Bankrupt

Brendan Fraser rose to fame for being the lead star in The Mummy trilogy and appearing in the comedy movie, George of the Jungle. Fraser was dealing with serious financial troubles after his divorce. The reason for his money problems was not confirmed, but rumors circulated that it might be due to child support payments that were said to be extremely high. We hope that he didn't have any other unpaid obligations at the time because, as we can imagine, it would have been hard on him to overcome every obstacle.

Heidi Montag & Spencer Pratt - Thought it Was the End of the World

You must be perfectly clued up on who Heidi Montag and Spencer Pratt are. Their first claim to fame was popular MTV reality show, The Hills. The series was going pretty well and the duo was earning a sizeable income, until they started to believe in the Mayan prediction that the end of the world was near. They spent all their money in anticipation of the Doomsday and were on the rocks. Thankfully, they have recovered from the earlier situation and are well on their way to become well-off again.

Janice Dickinson - Lost Money Because of Plastic Surgery Obsession

Janice Dickison used to be one of the most famous supermodels back in her day. She was at the top of her game in the late '70s and the beginning of '80s. Even though her fortune was fat, she ended up filing for bankruptcy. She had a debt of almost $1 million due to her obsession with changing her looks. She may need to think profoundly with regards to how she spends her money because insisting on having appointments with plastic surgeons is no good for her pockets. We love her just like she is!

Chris Tucker – Rush Hour Superstar in Massive Debt of $11 Million

Chris Tucker is mostly remembered for his acting stints in the famous Rush Hour movies. The first Rush Hour movie hit the theatres in 1998 and Chris also became the highest-paid actor in the industry and he had literally a lot of money to burn. However, being wealthy does not always mean that people would pay their dues religiously. His tax deficit soared up to $11 million and had to sell his mansions. Eventually, he took a refinance loan and repaid all his debts. Let’s hope he will not go back to his old ways after that!

Rihanna - Blamed it on Her Accountant 

Rihanna is one of the most famous musicians these days. We're not shocked that her accounts have swollen tremendously over the years. Unluckily, her personal business finance accountant made some questionable financial decisions which led to her losing around $9 million. Rihanna found an excellent counsellor later who helped her recover some of the lost money. With her current net worth of around $85 million, she is probably doing just fine for herself, although she must be more vigilant, for sure, when it comes to her finances after her past adventure.

Teresa Giudice - Jailed for One Year and Three Months

Teresa Giudice is a well-known name since she appeared on the popular reality show The Real Housewives of New Jersey. Among all other participants, Teresa was among the highest paid ones. After the show had ended, Teresa and her husband needed a good lawyer with vast knowledge of criminal law since they faced some legal issues which led to their finances taking a dive. They stayed in prison for one year and three months after being charged with conspiracy and fraud. Life is not always easy on our beloved celebrities.

50 Cent - Lost His Money to Creditors

Curtis Jackson is better known by his stage name 5o Cent. 50 Cent is one of the most recognized and respected rappers in the hip-hop industry. But even though he's very successful, he managed to owe an enormous amount of money to creditors. The rapper later needed a criminal lawyer as he faced a massive lawsuit. Thankfully, his lawyer had plenty of experience when it comes to such matters and so he managed to get him out of trouble. We hope that 50 Cent learned his lesson because we hate to see our favorite celebrities behind bars!

Kelis  - Extreme Child Support Payments

Kelis was in a great place back in the '90s. She was one of the most singers with her chart-topping hits. On the other hand, the singer wasn’t as fortunate when it comes to managing her finances. At the peak of her success, she visited a couple of divorce law firms as she had decided to end her marriage with her then husband. The implications of such an event along with the expenses when it comes to a child had the singer fell on hard times and is still struggling with money issues to this day.

Michael Jackson - Massive $500-Million Debt & A Foreclosed Property

Michael Jackson was the ultimate King of Pop, and he will always remain one of the greatest musicians of all time. The man was a multiple-award winning music legend. However, he was in massive debt since he owed $25 million just for his famous Neverland Ranch. Business finance was not his strong side, so the ranch was foreclosed. This was not all, however, as Michael had accumulated a total of $500 million in debts at the time of his death. It is hard to fathom how a celebrity of his size could ever face such problems, yet he could not have been successful in everything!

Larry King - Owed Over $360,000

No introduction is needed for Larry King is a famous radio and TV host with a huge career on his back. He received some major awards including ten Cable Ace Awards. For some celebrities, it is the end of their world when they are a step away from bankruptcy. But Larry was not too depressed when it happened to him. He had a debt of $360,000, but luck was on his side, and his slip up was only temporary. His show Larry King Live brought him massive income, and he never looked back after this.

TLC: Poor Royalties & Erratic Behavior

TLC may have been the sweethearts of the ‘90s R&B scene, but they are a long way off from their days of money, fame, and scrubs (props if you get that reference). The group filed for bankruptcy in 1995, citing poor royalties from their record label LaFace Records, and a breach of contract by their manager. Some would side with the girls, especially as their contract gave them only a measly 7% of the revenues of their first few records. The debt got worse because of damages that Left Eye paid after she allegedly burnt down an ex-boyfriend's house.

Allen Iverson: Gambler & ‘Bling-Bling’ Connoisseur

Allen Iverson may be a little farther from broke than most people on this list, but compared to his nearly $200 million in assets over a 15-year career, the retired NBA star doesn’t have an impressive bank account balance. Iverson lost a large part of his fortune to his inadvertent ability to live conservatively and an over-publicized divorce. The star’s bailout from an impending financial disaster was a deal with Reebok which someone in his inner circle scheduled to pay him only at much later date – thankfully, someone was looking out for him.

MC Hammer: A Big House & An Entourage the Size of a Small Village

Money, fame, and fortune are the idyllic reality of most hip-hop stars, and for MC Hammer, it was no different. After composing the most dance-worthy-beat of all time, Hammer amassed a million-dollar net worth that made him comfortable enough to purchase a deluxe mansion and hire staff and an entourage the size of a small village. The price of his financial crisis was his enormous love for outlandish things. It's a good thing he turned his life around and became a pastor. However, it is a little too late for his finances to make a full recovery.

Kim Basinger: Bought a Town

Kim Basinger’s money misadventure was riddled with mild controversy, especially since the Hollywood starlet rarely had money troubles. After purchasing the town of Braselton, Georgia for nearly her entire net worth, she was forced to sell it for a paltry $1 million to offset a settlement claim after being sued for pulling out from a production at the last minute. Eventually, Basinger declared bankruptcy and what followed were a throng of legal proceedings that were invasive of the star's total assets. Now, at her 65 years of age, we hope she knows a lot more about financial dealings.

Wayne Newton: Multiple Lawsuits

With a net worth of $100 million and $25 million in annual income, it should be nearly impossible to imagine Wayne Newton going bankrupt. But celebrities have been known to opting for a life of comfort for their love of extravagance. For Newton, his downfall was the result of grandiose purchases and bad investments. To top things off, the entertainer has been sued multiple times since 1992, a fact that must have had quite an impact on his financial state. Sometimes, though, these experiences turn into great lessons. Let’s hope Newton is a good student!

Terrell Owens: A Lethal Combination of Bad Investments & Women

Terrell Owens is a part of the unfortunate statistic of NFL players who go bankrupt only a few years after having retired. After playing for 15 seasons in the NFL, the star should boast a net worth of at least $80 million, but a lethal combination of poor investing decisions and substantial child support payments has Owens scrambling for crumbs of his remaining money. These days, the former NFL star is neither able to land an NFL job nor pay child support. We hope that he remains positive, though, and that things will get better soon!

Tionne “T-Boz” Watkins: Being a Scrub

After a poor recording contract caused her group to slip and fall into the financial red, TLC filed for bankruptcy in 1995. Long after their collective money woes were somewhat over, TLC's Tionne has yet to make a full recovery. The singer has reportedly gone bankrupt twice since the initial 1995 and is said to be on the hook for almost $800,000 to be repaid. Her debt was reported to result from various costly dues of hers. With her monthly income at merely $11,700 – a debt-free future may not be in sight.

Tammy Wynette: Bad Investment

Despite enjoying a relatively successful career from the late '70s through the '90s, country singer Tammy Wynette was in a dreadful financial state in 1988 after a lousy investment caused her to lose nearly all her initial assets. Wynette reportedly invested most of her money in two shopping malls in Florida but ended up losing all of it when the malls failed – her salvation was her active career which brought her debt relief over time. Otherwise, the levy on her house and other assets were guaranteed to see her homeless and needy in no time.

Warren Sapp: Karma

It's sad when someone made $82 million in his NFL career but ended up with just $826.04 in his bank account. It could befall even the best of us. But when it is Warren Sapp, who had a lion skin rug, de Grisogono watch, and 240 pairs of sneakers, it's easy to see how he could go from the All-NFL penthouse to the rather modest basement. Add the shoes to the women, his children’ income, and having no other means to get financed - and what you have is 78% of former NFL players who go bankrupt within two years of leaving the sport.

Tia Carrere: Made A Bad Deal

After gaining TV repute for her role on ABC's General Hospital, Tia Carrere became a force to be reckoned with – especially by bank account standards. But shortly after her breakout role, and subsequent part in the series A-Team, Carrere was short of money, and her earnings barely matched her expenses. Soon enough, the actress filed for bankruptcy with $50,000 in debts. Unfortunately, an earlier agreement with ABC disallowed her from taking on other roles, even though her salary was dwindling. Thankfully, Wayne's World in 1992 had saved her.

Drake Bell: Betting Future Income Against Loans

If there is anything we can learn about Drake Bell’s bankruptcy claim, it is that betting your future income against loans is dangerous. The star came to prominence after the Nickelodeon show, Drake, and Josh but after making $408,000 in 2012, he made a measly $14,099 in 2013 and slipped into a financial rut. Despite the bank foreclosing his property and managing to rake in earnings of $2,000 a month, his expenses exceeded his earnings. Speculations suggest that his rift with co-star Josh may be related to his new bank account balance.

Joan Rivers: Bad Loans & Joblessness

The world is undoubtedly a duller place without the controversial comedian Joan Rivers, but before her passing at 81,  the TV personality, author, scriptwriter, and businesswoman left a mark in Hollywood. After losing her husband to suicide in 1987, Rivers was in her mid-50s, bankrupt, and jobless. But as soon as she appeared to have had a slip and fall, she managed to pick herself up and out of a $37-million debt, gained remarkable Hollywood repute and garnered a net worth of $150 million. Only a woman like Rivers can pull that off.

Gary Coleman: Thieving Parents & Recurrent Health Problems

Most people recognize Diff'rent Strokes star, Gary Coleman, who entertained the audience in the ‘80s through ’90s. But Coleman would slip and fall into a fatal combination of health woes, stagnant career, and money troubles. In 1990, Coleman's net worth reportedly surpassed $5 million; but by the end of Diff'rent Strokes, he was in a nasty court battle with his adoptive parents who allegedly stole as much as $1 million from his estate. With the legal fees and a failing health, his bank account barely stood a chance. Coleman died in 2010 at age 42.

Dustin Diamond: Mismanagement

Best known as Screech on the '80s-'90s sitcom, Saved By the Bell, Dustin Diamond was the typical '80s child star whose earnings were beyond impressive. Unfortunately, after Saved by the Bell, the actor wasn’t offered other roles, and his money troubles began to unravel. Decades later, America’s beloved nerd was forced to file for bankruptcy and faced foreclosure of his Wisconsin home. He blamed his parents for spending lavishly his acting earnings, and eventually, he was forced to sell T-shirts to save his home from the bank.

Teri Polo: A Ton of Debt

While reports suggest that Teri Polo’s earnings go to regular living expenses, all of which are within her means, the actress somehow managed to rake in almost a million dollars in debt. You would think that after starring in Meet the Parents, Meet The Fockers, and Little Fockers, Polo’s bank account would be bursting at the seams, but she filed for bankruptcy in 2014 citing debts to the IRS, credit card debt, and $30,000 in a settlement claim by her former landlord. With barely $50,000 in total net worth, it would be impossible to meet the payments.

Helen Hunt: Tax Evasion

Technically, Helen Hunt never went bankrupt, but sources reveal that her taxes seem to have given her a mild bankruptcy scare. The award-winning actress starred in Hollywood hits, including Twister, Cast Away, What Women Want, and As Good As It Gets. Despite enjoying a flourishing career along with its dividends, the actress racked up quite some money in taxes but had sufficient assets in liquid cash and property to pay off her debt before too many people caught wind of it.

Mark Twain: One Bad Investment

One of the most successful writers in history, Mark Twain struck literary gold when he wrote a story that was published by the Saturday press in New York. Over the course of his career, his earnings skyrocketed into millions of dollars (in these days), except for one lousy investment that had him stuck in debt. After investing a large chunk of money in a publishing house and a Paige typesetting machine, his business failed. But then, it's not over unless you stop trying - so he had paid off his debt and had a net worth of $600,000 when he died.

Tom Petty: Contract Renegotiation

By his account, Tom Petty and his bandmates barely received anything from the profits of their first two records. But rather than stay stuck and accept measly earnings, in a preemptive move, Petty took full responsibility for the production of their 3^rd album and became indebted by $500K. He then filed for bankruptcy to try to nullify his contract. He won after being signed under a favorable deal with MCA's new subsidiary, Backstreet Records. In the end, he reaped the dividends of his ‘smart’ work and got back his money, and more.

Mick Fleetwood: Drugs & Lavish Purchases

Fleetwood Mac drummer Mick may have first declared bankruptcy in 1984, but, he admits he has lost count of how many times he has gone bankrupt since his initial filing. The unrepentant star spent his earnings on cocaine and impulsive purchases including several homes, a $40,0,000 spread in Hawaii, and a $1.8-million farm outside Sydney, Australia. The dividends of his reckless spending caught up with him, and it wasn’t long before his property faced foreclosure, and he was forced to put his ‘kingdom’ up for sale to bail himself out of the rut.

Jon Gosselin: Divorce & Custody Battles

Jon and Kate Gosselin eased into fame following the success of their controversial reality show, Jon & Kate. After the odd couple parted ways in a nasty divorce, John faced money troubles while his ex-wife received up to $40,000 in earnings per episode of her new show Kate plus 8. Between getting slammed with a million dollar lawsuit against his former employer and a custody battle with his ex-wife, John was left with enough reasons to declare bankruptcy and was reduced to starting a Go Fund Me page, to help pay off $30,000 in family court fees.

Ulysses S. Grant: Notoriously Unlucky in Business

Former President Ulysses S. Grant may have been a remarkable leader, but he was not as skilled in business. Grant spent a decade in the army and resigned in 1854 with distinction, but over the next years, he failed as a farmer, real estate agent, and then rent collector. Things didn’t even go smoothly with when he tried to sell firewood on street corners during the civil war. With nearly zero earnings and a portfolio of failures, he managed to make it to the White House, only to get involved in a dangerous investment after leaving the presidency.

Debbie Reynold: Failed Business & Marriage

Hollywood legend Debbie Reynolds suffered a fair share of money and marriage misfortunes in her day. Between her multiple divorce proceedings and her failed Debbie Reynolds Hotel and Casino, the actress/dancer who once boasted a net worth of nearly $60 million could barely stay afloat and filed for bankruptcy shortly after her second husband left her neck deep in debt. Before her death at age 84, Reynolds managed to turn things around after her time-share financier David Siegel took over management of the hotel to help it recover.

Dionne Warwick: Financial Mismanagement

While a lot of celebrity bankruptcy cases are shocking, the question of Dionne Warwick’s money troubles is beyond baffling. The icon not only raked in monthly earnings of $100,000 at the peak of her career, but she also has two children’s books, a best-selling autobiography, and a fragrance line to her credit. At the time of her petition, Warwick barely had any property and could scarcely boast a $25,000 net worth. No wonder her $10 million in unpaid taxes were merely allowed to slide.

Joe Francis:  Gambling

Joe Francis may have made a fortune out of persuading drunk girls to do inappropriate things that would humiliate themselves but earn him money, but the sleazy money bag soon learned that he couldn’t always have his way just by talking. After the Girls Gone Wild Empire crumbled from financial woes and court-ordered sanctions, he declared bankruptcy in 2013 at which time he already had a $2-million gambling debt and didn’t want to sell his property to settle the bill.

Aaron Carter: Mismanagement

After raking in $2 million in taxes, one-time teen heartthrob Aaron Carter filed for bankruptcy in 2013 with barely any of his earnings from his days as a star to show for his hard work. The younger brother of the Backstreet Boys proved that being famous doesn’t always mean having money in the bank. And after a business affair with his parents went south, Carter would have to surrender his listed property – including his dog, bringing his net worth to zero dollars. At the time of his petition, he barely had $900 in his checking account.

Abby Lee Miller: Attempted Bankruptcy Fraud

In a bid to hide hundreds of thousands of dollars in income she received for appearing on the favorite Lifetime show, Abby Lee Miller, the no-nonsense star of Dance Moms, smuggled more than $120,000 in Australian currency into the U.S. But her fame only made her crimes more noticeable, and she eventually pleaded guilty to bankruptcy fraud in 2016. She was sentenced to one year in prison and ordered to pay $40,000 in fines.

David Cassidy: Loans, Divorce & DUI

Former teen idol David Cassidy is a long way off from his days as the dreamy teenage boy on every girl's wall. The actor fell on hard times recently and in a slew of DUI charges, alcohol and divorce troubles was forced to file for bankruptcy with claims that he owes $10 million in debt. His creditors include a lawyer, his bank (and a few others) and American Express. Given the current situation, it is hard to see how Cassidy can manage to claw out of debt especially with a dementia diagnosis and a retirement plan that will likely keep him off the screen.

Isaac Hayes: Mismanagement

Isaac Hayes was a great soul singer of the 20^th century.  To his credit, he created the Shaft theme song (for which he won an Academy Award in 1972),  as well as Soul Man, a hit for the duo Sam & Dave, and was inducted into the Rock & Roll Hall of Fame in 2002. Haye’s money problems began in the ‘70s and nearly derailed his career. After filing for bankruptcy in 1976, he admitted to hiring the wrong people to manage his finances. A family-sponsored project honored his legacy and raked in revenues for his estate after his passing.

Nicolas Cage  - His Shopping Spree Buried Him in Enormous Debt

Nicholas Cage is one of the most famous Hollywood actors, best known for his roles in the movies like National Treasure and Ghost Rider, just to name two. During his many years in the industry, he amassed a little fortune. However, he also accumulated a staggering debt of $14 million due to his spending spree on real estate, luxury cars, and yachts. We are sure that this is nothing that a refinance loan could not fix as Nicholas makes millions on a regular basis.

Shane Filan: Bad Property Investments

Former Westlife band leader Shane Filan sang his way out of poverty once, but a string of lousy property investments brought him back to his knees. Filan lost a whopping £18 million which was a combination of a loan and his total net worth. But even though he lost all his money and was weighed down by a lethal combination of debt and taxes, the singer admits that he found solace in his wife and kids. Two short years after the initial filing, Filan had paid off a large chunk of his debt and was reaping the dividends of his solo career.

Richard 'Fazer' Raws: Unpaid Taxes

After he admitted his inability to pay taxes, the rapper Richard Fazer Rawson had declared bankrupt. Court records showed that the celebrity merely managed to stay above water with earnings barely matching expenses. Soon, after nearly losing his livelihood and facing home foreclosure,  Rawson became a father and began exploring other options to make money for his new small home.

Duncan James: Failed Business

The Blue star filed for bankruptcy on September 12, 2013, after the band's company Blueworld went into administration in May. At the time he said: "In some strange way, it's actually a relief to have been declared bankrupt. It means I can start again. Before I went bankrupt, I had been trying to pay off loans for years and felt as if I was drowning."

Sherman Hemsley: Taxes & Loans

After playing George Jefferson on The Jeffersons, Sherman Helmsley boxed himself into a corner and eventually filed for bankruptcy after he could not pay $1 million worth of loans and taxes. Surprisingly, the money resurfaced and the actor and his creditors arrived at an out-of-court settlement. Whatever the case, the taxes were paid off, and Helmsley was a free man.

George Clinton: Shady Business Deals

Completely oblivious that his business partners and managers took ownership of the publishing rights to all his music, George Clinton simply waltzed through his career without an eye on how much money he was worth, and how much his earnings were. Retirement could have now been in view but by 1984, Mr. Clinton, unfortunately, filed for bankruptcy to avoid an economic mess. Soon enough, he was able to make it out of the rut alive and will undoubtedly be wary of future collaborations.

James Hetfield: Alcohol & drugs

After making his name for being part of the most memorable rock band ever to exist – Metallica, James Hetfield declared bankruptcy after his longtime drinking of excessive alcohol and being addicted to extracurricular drugs depleted the singer's earnings. Currently, the entire band is far from retirement because they have to tour every summer to make up for the loss, and James Hetfield is stuck with payments on mortgage and taxes. Perhaps one day soon he will make a full recovery.

Michael Vick  - Imprisoned for Running A Dogfighting Ring

Michael Vick is a well-known name in the world of NFL. Michael is a former quarterback, and at one point, he was among the highest paid players in the industry. However, soon after he finished his sports career, he had to get himself a good felony lawyer, since he faced charges for running an illegal dogfighting ring. When he was finally out of jail, he filed for bankruptcy.

Dennis Rodman - His Expensive Divorce Led To His Bankruptcy

When it comes to the National Basketball Association, Dennis Rodman used to be one of the most recognized names in the game. However, Dennis faced financial difficulties when he filed for divorce for the third time. Due to high child support payments, his debt climbed to more than $800,000. So the logical step was for Rodman to file for bankruptcy. On the other hand, he is a good candidate for mortgage refinance, and with some banking bailouts, he will surely get back on his feet.

Dorothy Hamill - Ice Capades Investment Led her to Bankruptcy

Dorothy Hamill is a retired figure skater, and back in her time, she was among the highest paid athletes. At the height of her career, she won many Gold Medals at the Olympics. Ice skating was her greatest passion, so she bought an ice skating company called Ice Capades. It was a financial misjudgment on her part since she was eventually forced to file for bankruptcy. Getting a business finance course from online universities and colleges might have helped her learn more about financial management.

Stephen Baldwin  - Millions in Mortgage Debts

Stephen Baldwin comes from a very wealthy family, and his older brother Alec is also a renowned actor like him. Stephen is best known for his performance on The Celebrity Apprentice and The Usual Suspects. Although he has been successful in the movie business, his finances had suffered since he accumulated a massive debt for an unpaid mortgage. We wonder if he thought of requesting a lowered refinance mortgage rate as a way out.

Mike Tyson - Had $50 Million in Mortgages

Mike Tyson is undoubtedly one of the greatest boxing legends whose life and career has been smeared with controversies a number of times. The former boxing star has apparently poor financial management skills, owing to which he suffered huge financial losses. We can confirm that he had a whopping mortgage of $50 million, and he needed to raise that amount to pay off the mortgage. He could ultimately raise that amount and we think he opted for mortgage refinance program at some point.

Courtney Love - Refused to Pay Her Mortgage

Courtney Love is one of those famous people whom you can almost instantly connect with revelry and bacchanalia. Her constant substance abuse has been the major reason behind her frequent trips to the drug rehabs. She also needed a criminal defense attorney at one point in her life as she was busted with drugs in her possession. Many of her fans do not know that Courtney also had a huge debt of $386,000 as she refused to pay back her mortgage. As a result, she lost her house and we can now only pray that she recovers from the financial instability.

Pamela Anderson - Luxury Lifestyle Resulted in a $1.7-Million Tax Debt

Pamela Anderson most certainly used to be every man’s dream woman when she appeared on the mega-popular TV show, Baywatch. We also enjoyed watching her in another TV show, V.I.P. During that time, her bank account was loaded, but over the top luxury lifestyle led her to accumulate $1.7 million in unpaid taxes, leading to her bankruptcy. Anderson had managed to pay her debt eventually (perhaps through a refinance loan).

Gary Busey  - Massive Debt to Creditors

Gary Busey is a famous American actor who appeared in over 150 movies, including Lethal Weapon and Predator 2. His career was on the right track, and he earned millions of dollars. However, five years ago, the actor had no choice but to file for bankruptcy since he owed his creditors a massive debt that reached millions. He also figured in a motorcycle accident which significantly affected his health (he didn't need a personal injury lawyer since he didn't hurt anyone). Busey needs to find himself a good business finance advisor to avoid such issues in the future.

Lady Gaga - Gambled Most of Her Money on Her Monster Ball Tour 

Lady Gaga has been one of the most controversial musicians in the industry ever since she appeared on the Pop music stage. She made a questionable decision when she gambled most of her money on her Monster Ball Tour in the hopes of scoring a major sponsorship deal. For a moment, this wild risk made her completely bankrupt, but it did pay off, as she managed to land a $40 million deal with the Live Nation, putting her back on track. We don't know what her private wealth management advisor (if she ever has one that is) would say to that.

Busta Rhymes - Spent More than He Could Afford

Busta Rhymes is the full name of one Trevor Smith. He is considered to be one of the most successful American rappers. Aside from rapping, he also dabbles in acting and record-producing. Sure, the money just kept coming in and his bank account couldn't complain, but he then went to spend more than he could afford for years. Today, he owes more than $800,000. He may consider finding an accredited online law school to teach him how to defend himself in court (if he won't be able to afford a criminal defense attorney) in case his creditors go after him legally.

Tori Spelling & Dean McDermott - Evicted from Their L.A. Mansion Due to Unpaid Rent

Tori Spelling and Dean McDermott are a famous Hollywood couple, and both of them are widely recognized names. It is not uncommon for rich Hollywood couples to spend a considerable amount of cash on luxury mansions but Tori and Dean couldn’t afford to pay their rental mansion. As a result, they got evicted. Fortunately, these two are good candidates so they can still apply for some of the best home loans out there should they want to have their very own house. But one advantage of renting is that one need not pay for the home insurance.

Lena Headey - Lost Money in Custody Battle

Lena Headey is in the prime of her career now, as she has become the 'alter ego' of Cersei Lannister from the very popular television show, Game of Thrones. It's hard to believe that someone like Lena going through a phase of financial instability, but he recently made an application for a mortgage refinance. However, we are not jumping to any conclusion here. We heard that she suffered a blow to her finances as she dragged her ex-partner to the court to resolve a dispute over the custody of their child. We think she could find out a child custody attorney who works pro bono or take up a money management online degree program or something like that.

Mickey Rooney: Mismanagement & Abuse

One of Hollywood’s most significant assets, Mickey Rooney enjoyed more than 80 years of career success and should have had a net worth nearing billions. But at the time of his death, his finance was in shambles, and his 8^th wife and son were alleged to have been physically abusing the star before his passing. Rooney’s money troubles began in 1962 when he first filed for bankruptcy with barely $500 in his account, at which time he was already married and divorced four times.

Nelly - His Gambling Addiction Led to Bankruptcy

Nelly was born as Cornell Iral Haynes. He has been among the most famous American rappers ever since he appeared on the hip-hop scene. However, Nelly developed a gambling addiction which eventually left him no choice but to file for bankruptcy. His tax debt quickly accumulated to a massive $2 million! He should consider visiting a facility for gambling addicts just like drug addicts who go to rehab centers for drugs.

Lauryn Hill - Jailed for Refusing to Pay Her Tax Obligations

Lauryn Hill is best known for her role in the widely popular group, Fugees. Later, she pursued a solo career which turned out to be a great decision. However, at one point, she did jail time for refusing to pay her income taxes. It appeared that she had the best criminal attorney and some wild luck as she is now a free woman. Most likely, her lawyer managed to get her a good deal with the state.

Marvin Gaye - Lived in a Van During His Most Difficult Moments

Marvin Gaye was truly a Soul music legend. During his fruitful career, he sold millions of records worldwide. In Gaye’s case, his success didn’t last long, and at some point, he was harshly burdened with business finance issues. He didn’t have any choice but to file for bankruptcy. He was even forced to live in his van before he moved to his parents’ house. Tragically, his father shot him to death in his sleep for reasons still unknown. But we do hope that it was not because of a life insurance on Gaye's head.

Zsa Zsa Gabor - Invested in Bernie Madoff’s Company

Zsa Zsa Gabor was one of the most famous Hollywood names back in her time. People would recognize her in the original 1952 film, Moulin Rouge. Even though she was an accomplished and wealthy actress, she had her share of financial difficulties. She had the misfortune of investing in American fraudster Bernie Madoff’s company. The decision proved to be an enormous financial mistake and she ended up with a debt of $10 million, which was an incredible amount of money at the time.

Leif Garrett - Lost His Entire Fortune to Drug Addiction

Leif Garrett was born under the name of Leif Per Nervik. Leif is a famous singer, television personality, and actor during the '70s. However, his career went downhill as he started experimenting with drugs. At that time, he lost all of his money and ended up in prison. When he was out of jail, he stayed at a center for alcohol and drug treatment to get better. Sadly, his fortune had long been gone.

Lorraine Bracco - Her Tough Custody Battle Drained All Her Money

Lorraine Bracco is a famous American actress that you probably know from her role on the mega-popular TV show, The Sopranos. While the show was doing well, her personal life wasn't. She had to look up divorce law firms since she wanted to end her second marriage. But what left her in dire straits was actually her long custody battle over her daughter with her ex-partner even before The Sopranos was put together. The legal fees alone had reached $2 million. We guess that the actress has recovered well and enjoying her now $24 million net worth.

Meat Loaf  - Betrayed by His Financial Advisor

Meat Loaf is a widely recognized name in the music industry, and we all remember some of his huge mega-hits. Meat Loaf is enjoying his retirement days now which he certainly deserved after so many years on the stage. However, in the past, he had serious wealth management issues since his financial advisor was stealing from him. In a cruel twist of fate, the same advisor also ended up suing him, which led to the former musician's filing for bankruptcy at one point.

Latoya Jackson: Ultra-Lavish Lifestyle

Micheal was the star of the Jackson family no doubt. Surprisingly, his sister Latoya Jackson was the first of the musically inclined family to be awarded a gold record. Latoya enjoyed a decent amount of success and proceeded to live a lavish lifestyle as she saw fit. It wasn’t long until she ran out of money and with retirement inching closer, she was forced to declare bankruptcy without any viable means to pay off her debt. Between paying a settlement of 650,000 and a debt of $500,000, Latoya was soon left with barely $50,000 to her name.

Evander Holyfield - More than $14 Million in Debt

Evander Holyfield used to be one of the biggest names in the boxing world. This Heavyweight Boxing Champion was considered as the greatest in his category ever. Holyfield was just like many other celebrities, so he went on shopping sprees, buying luxury houses, cars, and other expensive, unnecessary stuff. He wasn’t able to pay for many of these things, so he ended up with a debt of $14 million. Unfortunately for him, he wasn't a bona fide candidate for any refinance loan with such a track record.

R. Kelly - Mortgage on 20,000 square-foot Illinois Mansion

Robert Kelly, the ‘once best-selling musician’ whose dream of owning a luxury mansion was finally shattered and he is flat broke now. Not so long ago, Robert Kelly announced  that he was going to buy a 20,000-square –foot mansion in Illinios .But unfortunately, he could not pay back the 3.5 million $3.5 million mortgage which he took out for buying his dream home. The mansion was soon listed as a foreclosure property. Sad.

Meat Loaf: Court Disputes

After gaining popularity for the ‘80s hit, "I Would Do Anything For Love," Micheal Aday’s net worth skyrocketed to nearly $25 million. But then, after an ugly court battle with his former songwriting partner over the song, "Bat Out Of Hell,” Meatloaf was left a little short of money and one friendship poorer. Despite news of his bankruptcy and deteriorating health, he’s managed to resurface with a 2016 album that made it to the number 4 spot in the UK charts.

DMX - Addiction & 15 Children

After hitting it big with his 1999 five-time platinum album, ...And Then There Was X, DMX used to be one of the highest-selling hip-hop artists of all time. Between the music and his movies, including Cradle 2: The Grave and Exit Wound, he may have assumed that his bank account balance was invincible. Soon enough, drug payments, court proceedings, DUI, and child support payments for 15 children ate up his earnings as quickly as he made it. Now, he's one of the poorest rappers in the industry with nearly $10 million in debt!

Lindsay Lohan - Couldn’t Pay Rent on Time

Lindsay lohan is certainly a media’s baby, not just for her acting and singing skills, but for her changing relationship status and other controversies as well. Her frequent trips to the drug and alcohol rehab centers are an open secret now. She owed over $600,000 in credit card debt and couldn’t pay that back on time. She even went on the verge of becoming homeless. As you can assume, she did not pre-qualify for getting a home loan following the non-repayment of her credit card loan. Lohan’s case precisely tells us why intermittent credit checks are so important.

Toni Braxton - Filed for Bankruptcy Two Times

Toni Braxton is a famous American singer, pianist, actress, and record producer. You would think that there is no way that she might have any financial issues. But she had her share of money troubles as well. Even though she won numerous awards and sold an incredible number of albums, her lifestyle led to a massive debt of $50 million! Braxton filed for bankruptcy twice, so we highly doubt if she could get past a mortgage application if she ever needs one.

Jose Canseco - Refused to Pay His Income Taxes

Jose Canseco is one of those most recognizable names when it comes to the Major League Baseball history. On the other hand, Jose refused to pay his income taxes like some other celebrities on this list. He eventually accumulated an enormous debt so he filed for bankruptcy. We have no idea if he'd make a great refinance loan candidate, but he should start paying his obligations if he doesn't want to lose his properties. No general insurance would cover him or his possessions should this happen.

Natasha Lyonne - Financial Instability Aggravated by Health Issues

Natasha Lyonne became a huge name for doing the American Pie movies. After the final filming had ended, life was rough on Natasha. She ended up in some serious financial rut and also suffered from Hepatitis-C. She was not in any of alcohol rehab centers, but she looked like she was for a while. Fortunately, she was cast in the popular show Orange is the New Black, and now, the future looks much brighter for her.

Gary Dourdan: Joblessness

Despite being a pivotal part of the CSI cast for nine years, and landing a few small roles, Gary Dourdan filed for bankruptcy twice in the space of three years. The troubled actor owed quite some money in mortgage and child support payments as well as $110,000 in settlement to his ex-girlfriend for physically abusing her during their affair. With barely $312 in monthly earnings and $1.8 million in assets and property, a $1.7-million debt must certainly be an ordeal. And without any meaty project to offset his debt, the actor was stuck in a financial rut.

Walt Disney: Bad Investments & A Swindling Business Partner

Walt Disney started as a struggling filmmaker with barely enough money to pay his bills. After a bad investment and conniving business partner left him high and dry, Disney filed for bankruptcy in 1923. A few years later, he founded the Walt Disney Company on loan from his parents and debuted the character, Mickey Mouse. He came close to being bankrupt again while shooting the company’s first major production – Snow White and the Seven Dwarfs. But with another bailout from the bank, Disney was back on track – and the rest, they say, is history.

Burt Reynolds - Went Bankrupt Due to His Extravagant Spending

Burt Reynolds most certainly was one of the greatest Hollywood celebrities back in the '70s. At one point, his bank account was loaded as he used to be among the highest paid actors in the industry. An online business administration degree might have been helpful in his case since Reynolds ended up empty handed due to his love for luxury things. At his lowest point, his debt climbed to $9.4 million, and he had no choice but to file for bankruptcy.

Willie Nelson - $16 Million in Unpaid Taxes

Willie Nelson’s name is synonymous with great country music. He is indeed one of the greatest country singers of all time. Since Nelson is greatly respected, he earned his star at the Country Music Hall of Fame. However, he didn’t always make good financial decisions and ended up with a massive debt of $16 million. We guess then that he wasn’t a suitable candidate for mortgage application or refinance loan.

Wesley Snipes - Sentenced to a 3-year Jail Term For Tax Fraud & Evasion 

Wesley Snipes is another famous American actor on this list, best known for his role on the Blade movie series. Most Hollywood actors know how to handle their income taxes. They are aware of their obligations and the fact that the IRS will not stop until the taxes are paid in full. Well, Snipes went in the other direction deliberately, causing the government to press charges against him and demand the $12 million he owes the state. Even the best criminal attorney in the land could not save him.

Cyndi Lauper: Greedy Manager

Most celebrities go bankrupt after hitting it big, but for Cyndi Lauper, her slip and fall happened before she even had fame. The Girls Just Wanna Have Fun singer faced money troubles at the start of her career while in a band known as Blue Angel. After their debut album flopped and the group was disbanded, their ex-manager sued its members to the tune of $80,000. The court order forced the singer to declare bankruptcy, and take menial jobs just to get by. But after she went solo by 1983, her career took off. We must say that money changes everything.

Abraham Lincoln: Failed Business

If anything can dispel the stigma of being bankrupt, it is the fact that Abraham Lincoln, whose face now appears on the penny, once did not have any money to spare. After he became liable for $1,000 in back payments for a failing business, Lincoln’s debtors dragged him to court, and the former US President wound up paying his debts well into the 1840s since there were no modern bankruptcy laws to bail him out.

Sinbad: “I Invested In Myself & Other People”

David Adkins aka Sinbad may be good at making us laugh, but the Houseguest star proves that money troubles are no joking matter. Sinbad has filed twice for bankruptcy since 2009 with claims that his monthly earnings do not measure up to his debt. But even with more than $10 million in debt and barely $200,000 in his bank account, the comedian insists that he didn’t live extravagantly. He told Oprah, “I didn’t buy Bentleys, I didn’t live largely. I invested in me. I invested in a lot of other people. I would not change it; I would not go back.”