3.Willie Nelson
American original Willie Nelson was a pioneer of the “outlaw country” movement of the 1960s and ’70s, but the ’80s saw the singer become a real outlaw — in the eyes of the IRS.
For much of the decade, Nelson funneled his income into a tax shelter later deemed illegal by the agency. His tax bill totaled $16.7 million and forced the government to seize his assets in 1990, including his Texas ranch. Nelson eventually helped settle the debt by releasing a compilation album The IRS Tapes: Who’ll Buy My Memories?, the revenue from which he shared with the feds.
The singer, however, was able to keep his head up throughout, saying, “I had a lot of things I owned, I needed to get rid of,” he said. “I had a lot of people around and needed to back off and stop supporting half the world so I could stop and look at my situation. It’s given me time to take inventory.”
4.Walt Disney
Before he created the Magic Kingdom and built one of the largest movie production companies in the world, Walt Disney owned and operated an animation company called Laugh-O-Gram Studios.
Based in Kansas City, the company created animated fairy tales that were shown in local theaters. The Laugh-O-Grams became popular, leading Disney to seek a financial backer to support the endeavor.
But as luck would have it, the backing firm went broke and Laugh-O-Grams went bankrupt. While he tried to save his venture by living in his office and eating beans from a can, he eventually closed the studio.
Looking for a turn in fortune, Disney scrapped together enough money for a bus ticket and went to Hollywood, where he was able to make a very successful fresh start.
5.Larry King
The legendary talk-show host could have used his famous suspenders to hold up a wooden barrel. As any journalist will tell you, work in media doesn’t always pay the bills, and Larry King’s first gig in radio was no exception.
As a fledgling Miami radio announcer in the 1960s, King made no secret that he was “flying high,” despite the paltry salary that came along with the gig. But his money management troubles came to a head when he was arrested in 1971 and charged with grand larceny for allegedly stealing $5,000 from his business partner, Wall Street financier Louis Wolfson.
The charges were eventually dropped, but the dark mark on his career wasn’t, as he was fired from his radio jobs.
King wouldn’t hold a regular journalism job for more than four years, dropping him deeper into debt, to the tune of $352,000, and forcing him to declare bankruptcy in 1978.
That same year King was offered a late-night talk radio show in Washington, D.C., that eventually became his hugely successful eponymous CNN television show, which ran for 25 years.
6.Jerry Lee Lewis
Jerry Lee Lewis’s career is now in its seventh decade, so it’s no surprise that the “The Killer’s” career has had a few ups and downs. Lewis was kicked out of bible college for “playing the piano his own way,” but made it to Memphis just in time to get signed by the legendary owner of Sun Records Sam Phillips.
Soon after, Lewis released two smash singles — “Whole Lotta Shakin’ Goin’ On” and “Great Balls of Fire,” which helped launch rock n’ roll into the mainstream. However, Lewis’s scandalous marriage to his 13-year-old second cousin soon caused his career to all but collapse.
He returned to the charts in the 1960s, trading in rock n’ roll for country, but in 1988, he filed for bankruptcy, listing $3 million in medical, personal and tax debts
. But the music icon has rebounded once more, and at age 76, he’s still touring and is currently one of the subjects of the hit Broadway musical “Million Dollar Quartet.”
7.Anna Nicole Smith
The 27-year-old alleged golddigger thought her 90-year-old husband would leave her a hefty sum when he passed away in 1995 after their marriage of just over a year.
But when oil mogul J. Howard Marshall II bequeathed $0 to Anna Nicole Smith, Smith’s bank account read the same amount. She sued his $1.6 billion estate for a cut, claiming that Marshall had expressed his intention to set up a trust for her and alleging sabotage by Marshall’s son Pierce, who received the lion’s share of the money.
While the case was being fought, Smith was slapped with a judgment in a sexual harassment lawsuit by a former housekeeper. The judgment was based on perceived earnings from the estate, so Smith owed $850,000 in the case.
She was forced to declare bankruptcy in 1996, while continuing to fight for her $400 million portion of the Marshall estate.
But a series of legal flip-flops kept any money out of her hands, until her claim was finally rejected by the Supreme Court in 2011 – four years after her death.
8.Elton John
Perhaps it was the grand stage shows, extravagant parties and luxurious suits that led Elton John into financial distress. In 2002, the singer filed for bankruptcy after accruing debt at an astounding rate of $2 million a month.
With an estimated wealth near $265 million, five homes around the world and an extensive art collection, one would think that Sir Elton would have no problem saving money. But he has admitted to being an excessive spender.
In fact, before he filed for bankruptcy, the BBC reported that the singer’s credit card bills were averaging $400,000 a month.
That’s a whole lot of velour suits. Thankfully, Sir Elton got out of debt and has gone on to make many more millions — hopefully he’ll hold onto it this time.
9.Lawrence Taylor
During the 1980s, there were few linebackers in the NFL more feared than Lawrence Taylor. The 10-time Pro Bowler won two Super Bowls on the way to being inducted into the Pro Football Hall of Fame.
But like many pro-athletes, L.T. played hard off the field as well. “Crazy as it seems, there is a real relationship between wild, reckless abandon off the field and being that way on the field,” he said in 1987 near the height of his career.
Taylor claimed he could outdrink any other linebacker in the game and tested positive twice for cocaine use. Years after he retired, he claimed he would send prostitutes to the hotel rooms of opponents to tire them out before games.
While Taylor’s lifestyle didn’t come cheap (he once estimated that at his peak, he spent thousands of dollars a day on drugs), he didn’t help his cause with business decisions.
He started a company late in his career that was worth more than $10 million, then went bust. In 1997, he pled guilty to filing a false tax return in 1990. In 2009, Taylor filed for bankruptcy to avoid foreclosure on his home.
10.Gary Coleman
The late Gary Coleman, who was once the highest-paid actor on television for his role on “Diff’rent Strokes,” declared bankruptcy in 1999.
After a series of costly medical troubles and even costlier legal battles with his adoptive parents, the then 31-year-old claimed a $72,000 debt and filed for Chapter 7 bankruptcy. A decade prior, the actor reportedly boasted a $7 million fortune.
But he said he could “spread the blame” for his bankruptcy “from me to accountants to my adoptive parents, to agents to lawyers and back to me again.” The 4’8” star had difficulty landing steady jobs after his “Diff’rent Strokes” days, and after ongoing medical woes, passed away in 2010 at age 42.
Despite the considerable financial troubles he faced during the latter portion of his life, Coleman will always be remembered for uttering that iconic, million-dollar question: “Whatchoo talkin’ ’bout, Willis?”
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