Samuel Clemens better known by his pen name Mark Twain, was an American author and humorist. He may have died all the way back in the year of 1910, but he has still been a very influential man and author way passed his years of life. Author of The Adventures of Tom Sawyer and Adventures of Huckleberry Finn, he made a few too many investments that went bad and became so far in debt that he was forced to declare bankruptcy in the year of 1894.

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Sarah Ferguson is the former wife of Prince Andrew, Duke of York, the second son of Queen Elizabeth II and Prince Philip, Duke of Edinburgh. The raucous redhead had run up debts to the tune of $8 million by 2011. That year, she was also caught on video in a humiliating “cash for access” scandal, where she was filmed accepting money from a reporter, in exchange for an intro to Prince Andrew.

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Isley is an American recording artist, songwriter, record producer, and actor, and is best known as the lead singer and founding member of the family music group the Isley Brothers. He reportedly declared bankruptcy and failed to pay taxes several times during a three-year period. Afterward, the IRS seized cars, a yacht and property in 1997. His money problems eventually caught up to him then he was sentenced to three years in prison for tax evasion in 2006.

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Rihanna is a singer, actress, and fashion designer. In 2009 Rihanna went "effectively bankrupt" due to mismanagement of her fortune by her accountant. According to court docs, RiRi's chief bean counter blew through $9 million of her $11 million fortune in just one year. The singer sued the money manager and was awarded $10 million by the court, more than making her whole. Turns out, the $9 million is just chump change compared to the tens of millions she has earned since. Rihanna is reportedly worth close to $85 million today!

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Randy Quaid is an American actor and Golden Globe winner. In 2010 he lost $1 million in bonds after avoiding a court date on felony charges. Then, he and his wife, Evi, were arrested for squatting in a random Santa Barbara home. Finally, the conspiracy theorists decided they were to be the next victims of the “Hollywood Star Whackers” (a nonexistent star-murdering group that Quaid claims killed Heath Leger and David Carradine).

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Pamela Anderson is a Canadian-American actress, model, producer, author, activist, former showgirl, and a Playmate of the Month for Playboy magazine in February 1990, known for her roles on the television series Home Improvement, Baywatch, and V.I.P. In 2009 she was forced to move into a trailer park for owing over $800 thousand to the construction company that built her over-the-top Malibu mansion. She even skipped out on paying her $1.7 million tax bill.

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Nicolas Cage is an American actor and producer. His most popular films are Valley Girl, Birdy, Racing with the Moon, Peggy Sue Got Married, Moonstruck, Honeymoon in Vegas, The Rock, Con Air, City of Angels, Face/Off, and National Treasure. Nicolas decided to skip out on paying the $6 million he owed in taxes and was forced to put several of his properties on the market, and barely escaped filing bankruptcy. Even the salary from most of his film roles goes straight to the creditors.

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Natasha Lyonne is an American actress. She is best known for her role as Jessica in the American Pie series, and currently portrays Nicky Nichols in the Netflix series Orange Is the New Black, for which she received a nomination for the 2014.As well as staring in many other films. As a young child, she was signed by the Ford Modeling Agency then, at the age of six, was cast as a role in Pee-Wee's Playhouse. She has managed to make a great deal of money during her career as an actress; however, after she was diagnosed with Hepatitis C and a collapsed lung she went broke and was living in the streets.

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Natalie Cole is an American singer, songwriter, and performer. The daughter of Nat King Cole. After a career marked by award-winning success as an artist and personal lows as a heroin and crack addict, the talented singer went bankrupt in 1997, but by 2000 she had cleaned up her act and written a best-selling memoir Angel on My Shoulder. The book was adapted into a television movie that became a ratings bonanza.

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Mike Tyson is an American retired professional boxer, also known as Michael Gerard. This former undisputed heavyweight champion of the world is the youngest boxer to win the WBA, WBC, and IBF heavyweight titles at only 20 years old. He has made more than $400 million during his boxing career but in 2003 was forced to file for bankruptcy because of his life of luxury and tragic divorce with Robin Givens, that caused him debt of over $27 million. I guess that’s what you get for going through money like it is water! In a wholly original move, Tyson blamed scheming financial advisors, but the boxer has recently proven he still has a second act in him. His one man show Undisputed Truth became an off-Broadway hit and an HBO special directed by Spike Lee, by encouraging people to laugh at his pain he is quickly becoming a cultural icon once again.

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Mickey Rooney was an American actor of film, television, Broadway, radio, and vaudeville. Starting off as a child actor and moving up playing the role of Andy Hardy in many films, he was quite successful and talented. It was once stated that his personal fortune was worth about $12 million. However his popularity eventually began to dwindle, and by 1962 he filed for bankruptcy and listed his assets at only $500.

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Michael Vick was an American football quarterback for the New York Jets of the National Football League. He has previously played for the Atlanta Falcons and Philadelphia Eagles. He has been very successful in his football career. However, apparently all the money he earned was not enough. After Michael Vick spent 21 months in prison in 2008 for operating a dog-fighting ring, the former quarterback filed for bankruptcy. At one time, Michael was ranked the NFL’s 4th highest rated player by Forbes, to the tune of $37.5 million, but then the extravagance started. He supported a thirty-person entourage. He bought his mom a 7,800 square foot mansion. Business partners started investing obscene amounts of cash in silly businesses. After the dog-fighting scandal, the Atlanta Falcons quarterback went bankrupt in prison in 2008. In 2005, Vick was one of the highest-paid athletes in the world. By 2008, he was broke. Three years of splashing money around on mansions, a double-digit entourage and fruitless business ventures followed by the dog-fighting scandal cost the Atlanta Falcons player to lose almost every dime he had.

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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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