Marvin Gaye
Marvin Gaye's estate has an estimated net worth of $5 million.
Back in 1976, the Motown legend's divorce from his first wife, Anna Gordy Gaye, led him to file for bankruptcy. In order to cover the $600,000 Gaye owed his wife in alimony payments, the singer gave Anna the rights to his album "Here, My Dear."
Gaye was killed in 1984 when his own father shot him after a heated argument. The singer's financial troubles — along with drug addiction — followed him for the rest of his life, even though he continued to record albums and perform. He even moved to Europe in 1981 to avoid dealing with IRS.
Kim Basinger
When Kim Basinger filed for bankruptcy in 1993, the actress had a net worth of $5.4 million.
Her reason for filing for bankruptcy was backing out of filming the movie "Boxing Helena." Main Line Pictures sued her to the tune of $8.1 million for breach of contract. In a new trial three years later, Basinger settled for $3.8 million.
Basinger has since appeared in multiple films, including "8 Mile" and "Cellular," and she signed a contract with IMG Models — at 60 years old. As of last year, she had an estimated net worth of $36 million.
Meat Loaf
Meat Loaf currently has an estimated net worth of $25 million, a far cry from where he was a decades earlier.
The singer filed for bankruptcy in the '80s after Jim Steinman — who wrote many of Meat Loaf's songs — filed a lawsuit against Meat Loaf. This came just after the not-so-succesful release of Meat Loaf's album "Dead Ringer."
The singer's last hit album was released in 1993. He has since acted in movies (including "Fight Club"), released the TV series "VH1 Storytellers," and published an autobiography.
Willie Nelson
Willie Nelson currently has an estimated net worth of $25 million.
In the early 1980s, though, the country icon received one of the highest tax bills in history, after federal investigations found he had invested in a tax shelter that the IRS ruled illegal. Nelson was on the line for $16.7 million.
Although his lawyer negotiated the bill down to $6 million in cash, Nelson still couldn't afford to pay it. Instead, he ignored it, causing the IRS to raid his Texas ranch home and seize his assets — everything but his beloved guitar, which his daughter sent to him in Hawaii — in 1990.
The star made a unique deal with the IRS that some of the revenue from his album, "The IRS Tapes: Who'll Buy My Memories," would go towards his debt. He eventually paid it all off in 1993. Nelson has released multiple albums since, and will be on tour through the first half of 2015.
Dennis Rodman
In his NBA days, Dennis Rodman had a salary of $27 million, not including his endorsement deals.
After leaving the NBA, Rodman was struggling to pay his own bills. He couldn't keep up with all of his child support payments, which is why he ended up in court for the $809,000 he owed to his third wife in back child support — along with the $51,000 he owed her in back spousal support.
In 2014, after a trip to North Korea for a basketball game, Rodman checked into rehab for alcoholism. In September he said he would be returning in an effort to bring pro wrestling to North Korea.
Cyndi Lauper
Cyndi Lauper currently has an estimated net worth of $30 million.
The singer had a rough start, though. She spent four years singing and writing songs for the group Blue Angel. The group's "Polydor" album (released in 1980) never took off, causing Lauper to file for bankruptcy in 1981. She sang — dressed like a Geisha — in a Japanese restaurant and worked retail before releasing her hit album "She's So Unusual" in 1983.
In September, Lauper teamed up with singer/songwriter Sara Bareilles to record a song for the campaign Shine a Light, which raises money for pediatric cancer research.
MC Hammer
When rapper MC Hammer released his hit album "Please Hammer Don't Hurt 'Em" in 1990, he had an estimated net worth of $33 million.
Not long after, in 1996, Hammer filed for bankruptcy protection with a total of $1 million in assets and at least $10 million in debts. Years later, Hammer told Oprah Winfrey his debt wasn't a result of frivolous spending. He said, "I took my money and employed 200 people in my community. I had a payroll of a million dollars a month at times."
Hammer is now married with five children, and does everything from investing in internet startups to preaching to developing iPad apps. As of 2013, he reportedly still owed the IRS $800,000 in back taxes.
Francis Ford Coppola
When Francis Ford Coppola filed for bankruptcy protection — for the second time — his assets were listed at $52 million.
The director blamed the majority of his debt on the making of "One From The Heart," a movie which cost $27 million to film, but only earned $4 million. In 1992, when he filed for bankruptcy protection, Coppola had liabilities of $98 million.
Coppola has continued to direct — his most recent film, "The Bling Ring," came out in 2013. He owns a winery, which reopened in 2010, along with several boutique hotels.
Curt Schilling
Former MLB pitcher Curt Schilling earned just over $114 million during his 19-year career.
After retiring, Schilling sunk almost all of his net worth — $50 million — into founding a video game company, then lost his entire fortune when the company filed for bankruptcy in 2012. He was forced to sell many of his possessions (including his famous bloody sock and his $3 million Massachusetts home).
After an 8-month battle with cancer, Schilling went back to work in the 2014 as an analyst for ESPN, where he is now.
Larry King
Larry King currently has an estimated net worth of $150 million. However, at the time he filed for bankruptcy, he wasn't earning much working as a radio announcer in Miami.
The talk show host admitted that he was "flying high" back in the '60s during his time in Miami. In 1972, he was arrested for grand larceny and accused of stealing $5,000 from a business partner. The charges were eventually dropped, but King struggled to find a journalism job for several years thereafter. In 1978, he filed for bankruptcy with a total of $352,000 in debt. He was saved when CNN offered him a late-night talk radio show in Washington, D.C., that same year, which later became the famous "Larry King Live" that ran for 25 years.
King retired from CNN in 2010, but the host still does two web talk shows and "Larry King Now," which airs on Ora.tv.
Nicolas Cage
At one point, Nicolas Cage was one of the highest paid actors in Hollywood, earning up to $40 million per year. Between the years of 1996 and 2011, the actor earned over $150 million.
But Cage had expensive taste. He shelled out big money for things like exotic animals, private jets, mansions, and rare sports cars. In 2009, the actor owed $6.5 million in back taxes, and was being sued by his former business manager Samuel Levin.
As of 2012, Cage was still paying back what he owed in taxes. He is still acting in a number of films.
Mike Tyson
Mike Tyson earned a staggering $400 million over the course of his 20-year boxing career.
His earnings didn't exactly last him, though. The former heavyweight champion filed for bankruptcy in 2003, with a total of $23 million in debt. His debts included a $9 million divorce settlement, $13.4 million to the IRS, and $4 million to the British tax authorities.
Tyson released a memoir in 2013 and his TV show "Mike Tyson Mysteries" just finished its first season.
Floyd Mayweather
As of June 2014, it was estimated that Floyd Mayweather had earned over $100 million in 2014 alone. His current net worth is estimated at $295 million.
Lately, Mayweather has run into some financial trouble. In 2009, he defaulted on a $167,000 car loan. Three years later he filed a $61 million claim in a local bankruptcy case. Now, the IRS claims that Mayweather owes them $50 million in back taxes, and in the summer of 2014 it was reported he was "seeking the counsel of a lawyer to file for bankruptcy."
Mayweather is still boxing — no news on whether he's still spending the reported $75 million per year he used to.
Michael Jackson
It's unclear what Michael Jackson's exact net worth was when he died. His family put out a questionable estimate that his earnings would have been $40-$42 billion had he not died at 50.
But in 2005, when the pop legend was charged with child abuse, prosecutors thought he was on the edge of bankruptcy with $300 million in debt, and $400 million in liabilities. It was said that he was a millionaire who spent like a billionaire. Jackson's prosecutors tried using the star's financial trouble as evidence of his guilt in the case.
Jackson died in 2009 due to cardiac arrest. He was still in debt at the time of his death, and was hoping his upcoming comeback tour would help bring him out.
