Michael Jackson was an American singer, songwriter, record producer, dancer, and actor, who is also known as the King of Pop, had not always been rich. As a successful entertainer, he embarrassingly had to file for bankruptcy because he went too far with his life of luxury. He was forced to file for bankruptcy in 2007 when he was unable to pay back the loan for the Neverland Ranch that he had purchased.

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Meat Loaf is an American musician and actor, also known as Michael Lee Aday or Marvin Lee Aday. This musician and singer’s most famous songs is known worldwide is “I’d Do Anything for Love” and “Bat Out of Hell”. Throughout the mid to late 1980s, Meat Loaf began to experience a great deal of financial problems and was even forced to file for bankruptcy. To make matters worse, not only was Meat Loaf broke, but his ex-songwriting partner had also filed a lawsuit against him. Talk about bad luck! He declared bankruptcy in the mid-1980s.

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Marvin Gaye was an American singer-songwriter and musician. He helped to shape the sound of Motown Records in the 1960s with a string of hits, and he has sold multi-million dollar records which makes it quite unbelievable that he ended up going broke. In 1979, Marvin ended up filing for bankruptcy. According to Rolling Stone magazine, after Marvin went broke he ended up living in a bread van for a few years. How in the world did Marvin Gaye manage to go broke? The iconic crooner filed for bankruptcy in 1976 after a court ruled that the royalties from his upcoming album, Here, My Dear, were to be paid to his ex-wife for alimony.

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Marion Jones is a former world champion track and field athlete, a former professional basketball player for Tulsa Shock in the WNBA. She won 3 gold medals at the 2000 Summer Olympics in Sydney, Australia, and was the first woman to win five track-and-field medals at a single Olympics, but was later stripped of the titles after admitting doping. Not only did she admit to taking performance-enhancing drugs throughout her career, she was also down to a bank balance of only $2,000. Crazy in debt, she lost her mansion, two other properties and was stripped of her medals. These days, Jones is helping others to learn from her mistakes through her Take a Break program, encouraging young people to think twice before taking life-altering decisions.

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M.C. Hammer is an American rapper, dancer, entrepreneur, spokesman and actor, also known as Stanley Kirk Burrell. His songs feature outstanding dance moves and lyrics that rhyme and are quite catchy. At one point in his career his net worth was a whopping $33 million. However, his spending like crazy lifestyle dragged him into a huge amount of debt. He claimed to have at least 200 staff members that he was paying and even a $12 million mansion. In 1996 he was forced to file bankruptcy and has been struggling with money ever since! His outrageous spending, think luxury cars, airplanes, a record company, the largest entourage in celeb history, and a $30 million mansion, complete with a bowling alley, 17-car garage and a baseball diamond, has served as a cautionary tale to the newly famous. In the early '90s, the rapper was apparently 2 legit 2 live on a budget. He squandered his millions on a ridiculously extravagant lifestyle and was $13.7 million in debt when he filed for bankruptcy back in 1996.

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Lorraine Bracco is most famous for starring as Dr. Jennifer Melfi on the HBO series The Sopranos. Lorraine is now over 60 years old and has starred as Angela Rizzoli on the TNT series Rizzoli & Isles. After five long years of custody battle with her ex over their daughter Stella, Lorraine ended up filing for bankruptcy. As soon as she started more acting she was able to pay back her dept, but the bitter custody battle/divorce from Harvey Keitel had at one time left her penniless.

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Lindsay Lohan is an American actress, model, and singer. She began her career as a child fashion model when she was three, most famous for starring in the films The Parent Trap, Freaky Friday, and Mean Girls, she has had a great deal of success throughout her short life, and she is quite talented; however, she has run into a great deal of trouble. Being arrested, partying hard, car crashes, and a countless number of visits to rehab had caused the IRS to seize her bank accounts after she decided not to pay over $900,000 in back taxes.

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Lena Heady is an English actress and is most popularly known for starring in the popular television series Game of Thrones, for which she earned her an Emmy Award nomination for Outstanding Supporting Actress in a Drama Series.. Unfortunately she went completely broke after she was caught in an ugly divorce and a custody battle for her child. She went completely broke and lost all her money. She ended up having to sell her house just so she could afford to buy food!

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Leif Garrett is an American singer, actor and television personality. He became famous in the late 1970s as a child pop star and teen idol. He started his career as a child pop star and later turned to drugs which landed him a life full of trouble. Some of his most famous songs are “The Wanderer”, “Runaround Sue”, “Surfin’ USA”, “I Was Looking for Someone to Love”, and “Smells Like Teen Spirit”. He Garrett reported having only $350 in his bank account when he filed for bankruptcy!

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Lauryn Hill is an American singer songwriter, rapper, producer, and actress. She is best known for being a member of the Fugees and for her solo album, The Miseducation of Lauryn Hill. She has had an incredible music career and has made a great deal of money in just her short 39 years of life. However, in 2013 Lauryn served a three month prison sentence because she ended up not paying over $1.8 million in taxes. This is definitely ridiculous since she has made so much money while being a well known music artist.

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La Toya Jackson is an American singer, songwriter, author, television personality, actress, businesswoman, philanthropist, activist and former model. When singing didn't quite pan out as planned and she had to opt out of a contract early, she filed for Chapter 11 bankruptcy in 1995. These days, she's on more stable ground with a regular income from her reality show Life With La Toya.

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Larry King is an American television and radio host, actor, voice artist, and comedian whose work has been recognized with awards including two Peabodys and 10 Cable ACE Awards, who was over $350,000 in debt during the early 1970s. Larry was accused of grand larceny and decided to file for bankruptcy in the year of 1978, which, coincidentally, was the very same year he was offered his eponymous show.

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Kim Basinger is an American actress and former fashion model, and has had a career spanning nearly four decades, she has appeared in thirty-eight feature films, five television movies, and nine television series. She gained a majority of her fame when she played a Bond girl, Domino Petachi in Never Say Never Again. In 1989 she bought the town of Braselton, Georgia, and in 1993, she was sued by Main Line Pictures to pay for $7 million in damages due to backing out of a deal to star in the movie, Boxing Helena. Later that year she was forced to file for bankruptcy. After losing the lawsuit she was reduced to bankruptcy. She then had to sell the town.

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Joe Francis is an American entrepreneur and film producer who is best known as being the founder and creator of the Girls Gone Wild entertainment brand. Has been forced to declared bankruptcy after owing more than $16 million in disputed claims.

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Janice Dickinson is an American model, photographer, author and talent agent, she has been described as the very first supermodel. She has been a judge for four cycles on America’s Next Top Model. In 2013, the former model was reportedly over a million dollars in debt, half of which was owed to the government.

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Gary Dourdan is an American actor. He is best known for portraying Warrick Brown on the television series CSI: Crime Scene Investigation. In 2012 it was reported that he had $1.8 million in assets, but owed creditors $1.73 million. In court docs, he claimed that his monthly disposable income was only $321 after eight seasons on a hit television show. In 2012, Dourdan went broke and filed for bankruptcy.

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Gary Coleman was an American actor known for his childhood role as Arnold Jackson in Diff'rent Strokes. He lived a life full of success as a childhood actor and is known for his small stature. He struggled with his finances even though he had earned millions as a young child actor. In 1999, Coleman decided to file for bankruptcy because he only had $200,000 to his name because his parents and manager had wasted away all his trust funds.

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Gary Busey is an American actor, has appeared in many films throughout the 1970’s, 1980’s and 1990’s, and was nominated for an Academy Award for Best Actor in 1978 for his role in The Buddy Holly Story. Unfortunately this successful, but uncomfortably toothy character actor is a Financial Flop: With less than $50 thousand in assets and up to $1 million in debts, the 67-year-old Lethal Weapon actor filed for Chapter 7 bankruptcy in 2012.

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Evander Holyfield is a retired American professional boxer and he is a former Undisputed World Champion in both the cruiser weight and heavyweight divisions. He ended up having to sell his mansion to Rick Ross after he went through a foreclosure. He owed millions to the JP Morgan Chase financial firm, thousands to the IRS, and thousands in back child support.

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Dorothy Hamill is a retired American figure skater, and is the 1976 Olympic champion in ladies' singles and the 1976 World champion. Well known for her moves on the rink as well as her signature bobbed haircut. She has won many of awards and been very successful, including inductions into the Olympic Hall of Fame and the Figure Skating Hall of Fame, but despite all her success she still managed to end up broke. In 1995, she decided to buy the Ice Capades which ended up causing her to file for bankruptcy in 1996 with over $1.6 million in debt!

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Donald Trump is an American businessman, investor, television personality and author. He is the chairman and president of The Trump Organization and the founder of Trump Entertainment Resorts. Being wealthy is what everyone knows him to be. However, most do not know that lately Donald’s corporations have been suffering financially and his corporations have filed for bankruptcy. Even the billionaire himself has filed for bankruptcy four times, in 1991, 1992, 2004, and 2009. “I've used the laws of this country to pare debt,” he has said. “We'll have the company. We'll throw it into a chapter. We'll negotiate with the banks. We'll make a fantastic deal. It’s like on The Apprentice. It's not personal. It's just business.

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Dionne Warrick is an American singer, actress and TV-show host, who became a United Nations Global Ambassador for the Food and Agriculture Organization, and a United States Ambassador of Health. In mid-2013, she filed for bankruptcy after accruing more than $10 million in unpaid taxes and several consecutive years of negligent and gross financial mismanagement.

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Dennis Rodman is a retired American professional basketball player, who played for the Detroit Pistons, San Antonio Spurs, Chicago Bulls, Los Angeles Lakers, and Dallas Mavericks in the National Basketball Association. At 53 he went broke due to his alcohol addiction, drug use and way over spending.

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Debbie Reynolds is an American actress, singer, and dancer, most popularly known for starring in The Unsinkable Molly Brown. Had a hotel and casino went bankrupt in 1997. She had been trying to sell the property in the months before filing, but ultimately couldn't unload the Las Vegas resort.

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Cyndi Lauper is an American singer, songwriter, actress, and even a LGBT activist, who has had a career that has spanned over thirty years. She has had many songs that hit the charts, “Girls Just Want to Have Fun”, “True Colors”, “Time After Time”, “She Bop” and “All Through the Night”. In 1981 she was forced to file for bankruptcy after a mishap with her band Blue Angel’s record deal. However, shortly after this tragic event Lauper made a comeback with her new album and has been ranked #58 on VH1’s 100 Greatest Women of Rock & Roll.

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Courtney Love is an American alternative rock singer, songwriter, musician, actress, and visual artist. She has been in and out of the tabloids, who was once married to Kurt Cobain and when he died, she is said to have gone crazy. Her spending was out of control and she got into some serious debt. She ended up having to sell her home and even 25% of Nirvana’s music catalogue just so she could get out of debt. What a disaster! In In the early 2000s, the insane Mrs. Cobain discovered that members of her entourage had allegedly stolen $20 million of Kurt’s money. She began binging on drugs, fielding tax liens, and was eventually evicted from her sick West Village townhouse after setting it on fire.

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Chris Tucker is an American actor and comedian. He is best known for playing the role of Smokey in Friday and as Detective James Carter in the Rush Hour film series. He may have made a great deal of money during his career, but still went broke. In 2007 Chris Tucker was named the highest paid actor in Hollywood for the movie Rush Hour 3. A few short years later, Chris ended up owing $11 million in back taxes. The IRS went after Chris for a long time. Chris finally decided the only way for him to pay back all this money was to sell two of his mansions he had in Florida and one he had in Los Angeles.

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