Many people dream of making it big and becoming rich. But once you become wealthy, it’s not
10. 50 Cent
The “In Da Club” rapper was responsible for some of the catchiest hip-hop songs on the radio in the mid-2000s, but that wasn’t enough to keep 50 Cent financially sound. 50 Cent rose to fame when Eminem heard his “Guess Who’s Back?” CD and flew him to Los Angelas to meet Dr. Dre. 50 signed a $1 million contract, eventually parlaying that into much more as he became one of the richest rappers in the game. Like fellow rapper and entrepreneur Jay-Z, 50 Cent became heavily invested in the stock market.
Although he was the fifth-richest American rapper in 2014 with a net worth of $140 million, that dwindled within the span of a year. The rapper made international headlines on July 13, 2015, when he filed for Chapter 11 bankruptcy with a debt of $32,509,549.
9. Mark Twain
Mark Twain (born Samuel Clemens) wasn’t one of those artists who’s work only made him a fortune after his death. Twain, who penned such American classics as “The Adventures of Tom Sawyer” and “Adventures of Huckleberry Finn,” enjoyed a wealthy lifestyle for much of his professional career as an author.
Though he was a brilliant writer, Twain was not very business-savvy. He frequently invested in failed businesses and lost quite a bit of his fortune that way. In particular, his massive investment in the Paige Compositor, a complicated and imprecise typesetter, led him to declare bankruptcy in 1894.
8. Wayne Newton
Many of the richest people who became bankrupt were popular entertainers. In 1983, the Guinness Book of World Records named singer and performer Wayne Newton the highest-paid entertainer in the world. Despite his enormous income, bad business investments led Newton to amass a fortune in debt to the tune of $20 million. In 1992, the Vegas icon filed for Chapter 11 bankruptcy.
7. Francis Ford Coppola
It’s almost impossible to imagine having any financial difficulties after writing, producing, and directing many famous movies. Still, Francis Ford Cappola, who also created classic films filed for bankruptcy thrice in ten years. Mr. Cappola also created very unsuccessful films which resulted in a $71 million debt for Cappola, making him one of the richest people who became bankrupt.
6. Meat Loaf
Many people scoff when they hear rocker Michael Lee Aday’s stage name, but the man has sold some records. His album “Bat Out of Hell” sold more than 43 million copies worldwide, and still sells about 200,000 copies a year, 40 years after its release.
Things took a turn for the worse in 1984 when Meat Loaf rushed production on the album “Bad Attitude,” his wife had a breakdown on tour, and his album “Blind Before I Stop” was a massive flop. The album’s disastrous sales, as well as a lawsuit filed against him by a former partner, led to bankruptcy for the entertainer. But with “Bat Out of Hell” still doing well, Mr. Loaf can still probably make ends “meat.”
5. Ulysses S. Grant
Where else will Ulysses S. Grant follow Meat Loaf on a Top 10 list? Meat Loaf is a rock star, and Grant helped Lincoln free the slaves during the civil war, but the two men do have something in common: bankruptcy.
After he left office in 1887, Grant moved to New York City and invested most of his money in a Wall Street firm called Grant and Ward that his son co-owned. But his son’s partner turned out to be a thief, bankrupting the firm and Grant in 1884.
4. Mickey Rooney
The way bankruptcy works, most of the richest people who became bankrupt were able to file Chapter 11 with plenty of money still in their pockets. They just owed a lot of debt. But not Mickey Rooney, who valued his assets at just $500 when he filed for bankruptcy.
Rooney was an immensely popular actor in both Hollywood and on Broadway, netting $12 million at when his career peaked in the 1940s. (Hey, that was a lot back then!) But Vanity Fair called him “the original Hollywood trainwreck.” He spent his fortune on addiction and eight marriages. Still, he lived a long life, dying at 93 in 2014.
3. M.C. Hammer
M.C. Hammer may go down as history’s most profitable one-hit wonder. Forbes once estimated his worth at $33 million, but when friends and relatives constantly hit him up for cash, he was never able to say “U Can’t Touch This.”
Hammer’s high-profile bankruptcy came in 1996 when uncontrollable spending habits put the rapper $13 million in debt. His financial troubles became the fodder of late night television show hosts everywhere, resulting in hundreds of lame “U Can’t Touch This” jokes.
2. Thomas Jefferson
When you hear politicians talking about personal responsibility these days, they’ll often reference the Founding Fathers. But did you know that the author of the Declaration of Independence filed for bankruptcy several times? The reason may surprise you: he blew through much of his money wining and dining his friends. A modern day baller! Unfortunately, Jefferson was never able to get back on his feet. He died poor.
1. Willie Nelson
Willie Nelson is undisputedly one of the most successful country artists of all time. He has also acted in more than 30 movies and co-written several books. Nelson amassed such a fortune that in 1990, he owed the IRS $16.7 million in back taxes. They raided his home and seized his assets.
Here’s where things get interesting: rather than filing for bankruptcy, Nelson struck a recording deal with the IRS. You read that right. Nelson’s 1992 album “The IRS Tapes: Who’ll Buy My Memories?” raised $3.6 million for the IRS and was critically acclaimed.