Mortgage payments, credit cards, and tax debts. Living large for these
country stars no matter how famous they were surely had its downsides.
Here's a crappy scenario: You're a singer-songwriter who's written and performed
hundreds of songs, some more popular than others. At one point, you plan to let your children
inherit the rights to these songs. But sadly, you have to sell them in order to pull yourself out
of a deep financial hole. That's exactly what happened to the late, beloved country singer
Merle Haggard, who filed for Chapter 11 in 1992 after reportedly being 5 million dollars in debt.
"I think this is all for my benefit, to stand back and appraise things where
nobody can touch me for a little bit. Hopefully, I won't be in there long."
The Los Angeles Times reported that a chunk of Haggard's money problems stemmed from tax
issues. Rolling Stone said bad business moves and a string of divorces also contributed, as Haggard
was married five times. Plus, the singer had a contentious relationship with his label, Curb
Records, and accused them of stalling his career. So, in order to help pull himself out of debt,
the Oildale, California native sold 600 of his songs to Sony-Tree Publishing for over 3 million
dollars. And on top of that, he had to sell hundreds of acres of his own personal property.
Since releasing her first album, "Leave the Light On," country music singer Lorrie Morgan
had cemented her status as a well-established star in the music industry. By 2008,
her assets had reportedly grown to between 500,000 and 1 million dollars. 5 years prior,
she purchased a home in the charming town of Gallatin Tennessee.
Despite her asset growth, Morgan found herself in serious money problems, accumulating millions in
debt, and ultimately having to file for Chapter 7 bankruptcy. To make matters more complicated,
she made this decision on the heels of filing for divorce from Sammy Kershaw,
another famous country singer. SunTrust Bank also came for her home, which was said
to be a colossal 4,700 square feet, after owing over $17,000 in mortgage payments.
"It was the biggest mistake of my life that I didn't watch my own money. And I would say
to anybody: You have an accountant that does your money? You audit them… because one day
you're going to wake up and go, 'What do you mean I don't have any money?' ... Make it,
put it away, and save it because just as quick as you go up, you come back down."
Similar to Eddie Montgomery, Sammy Kershaw’a business went belly up,
and got him into all kinds of troubling debt. Kershaw started Hotchickens.com in Whites Creek,
Tennessee, with Lorrie Morgan before they split in 2007. But when the restaurant closed,
the creditors came knocking. The Nashville Post reported that Kershaw’s debt indicated
in his Chapter 13 filing ranged between $100,000 to $1 million.
On top of that, Kershaw, who was dropped by his label Mercury Records in 2000,
owed $89,676 in alimony payments to his ex-wife Kim Kershaw.
“Those two are gonna fall in love tonight and spend the rest of their
life together, only they don’t know it yet.”
His debt was also accumulated through credit card purchases, bus leases, self-storage costs, and
back taxes. On top of that, several vendors sued him for non-payment. Kershaw spoke about his money
problems with The Boot in 2010, and it seemed like he regretted filing for bankruptcy, saying,
"I don't recommend bankruptcy to anybody if you can work it out… A lot of people are willing to
help and work with you, but sometimes there's a point where even the little bit of help don't
help anymore. My advice is to do everything you can to avoid bankruptcy because it is a tough
thing to get over. It's a tough thing to start over ... Your credit is shot for a long time."
There have been times throughout music history when singers used their art to settle a legal
matter. In 1978, for example, Marvin Gaye released "Here, My Dear" and used the royalties
to pay alimony to his ex-wife, Anna Gordy Gaye. In 1991, in order to pay off a massive tax debt
of $16.7 million, Willie Nelson released his LP "The IRS Tapes: Who'll Buy My Memories?".
The amount was whittled down to $6 million, thanks to Nelson's lawyer. But after the star
failed to pay that amount, the feds raided his home in 1990 and seized his assets,
including his recording studio, instruments, and other properties.
Later, the IRS allowed the country legend to pay off the debt with his "Who'll Buy
My Memories?" album, but he needed to sell four million copies. Based
on the financial split that was agreed upon with those involved in the album,
the IRS received just $3.6 million. Thankfully for Nelson, he was able to pay off the remaining debt
in the following years. He reminisced with the New York Times in 1991 about the situation, saying:
"I thought they'd be crazy not to take it. The very fact they
see a way to make a lot of money real quick made them go for it. They're not
interested in sitting around waiting 10 or 20 years for the money to trickle in."
Kenny Rogers, Alan Jackson, and Florida Georgia Line. These are just a few country
artists who've opened restaurants. As of 2023, all of their eateries are still open. But sadly,
the same cannot be said for Eddie Montgomery's Steakhouse in Harrodsburg,
Kentucky. Montgomery, who was one half of the country duo Montgomery Gentry,
launched the steakhouse in 2009 with his wife Tracy Nunan.
“Basically, we wanna build a stage and
build a restaurant and bar around it. So that’s kinda what I did. Hahaha.”
But by 2010, the couple was no longer married, and three years after that, the steakhouse was
closed. The business failed as Montgomery had to take out some hefty business loans and,
in turn, accumulated 12.7 million dollars of debt. In 2013, he filed for bankruptcy.
Whether or not Montgomery could afford his lifestyle is a matter of opinion for those
outside of his financial situation. But he and his ex-wife lived in a home in Perryville, Kentucky
that sat on 273 acres of land. So, it's possible the property was costly to maintain. But, that's
not the reason the bankruptcy was filed, according to Montgomery's lawyer, Jamie Harris. He said,
"It is very common with individuals dealing with divorce and business
closure to have to seek out bankruptcy trying to maintain a restaurant."