The Rise and Fall of the Conway Twitty Empire

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Conway Twitty was one of the most successful country music artists in history. With forty #1 songs on the Billboard Hot Country Songs chart, only George Strait secured more #1’s over his career. Nicknamed the “High Priest of Country Music” by country comedian Jerry Clower, Conway Twitty left a crater of an impact in country music not just with his own songs and albums, but also through his legendary duets with Loretta Lynn, which included 10 total albums, five #1 singles, and twelve total Top 10 hits all on their own.

During his era, Conway Twitty was like country music’s version of Elvis Presley, and not just from his genre-leading success. Twitty actually started in rockabilly and rock ‘n roll, wrote songs for Elvis, and had a similar look to The King with his pompadour and mutton chops. Though this made Conway’s music cool and accessible to a large audience, this always kept him at arm’s length from some country purists. And despite his incredible success, Conway’s only CMA Awards came through his collaborations with Loretta Lynn.

Twitty was also a gifted songwriter, penning eleven of his #1 hits. Scores of other performers recorded Conway Twitty songs as well. Conway’s contributions to country music were massive, but you don’t always hear his name considered when people rattle off their Mount Rushmore of artists in the genre. There are probably a number of reasons for that.

One reason is that Conway Twitty passed away at the relatively young age of 59, denying him that Golden Era victory lap that helps secure the legacies of some artists. Another reason is that some of Conway’s biggest songs may seem a little risque to the modern ear. Songs like “I Can Tell You’ve Never Been This Far Before” and “I’ve Already Loved You In My Mind” probably couldn’t be recorded and released today, though it was Conway’s sex appeal that was also part of his popularity.

For years, large portions of Conway’s catalog were out-of-print. This made it even more difficult for country fans to remain connected to Conway, and for new listeners to take those deep dives into his music.

But perhaps the biggest reason that Conway Twitty’s legacy has somewhat disappeared is that he wasn’t the sharpest of businessmen. Despite being as big as Elvis for a spell and building his own version of Graceland called Twitty City in Hendersonville, Tennessee, it all eventually came crashing down due to an estate dispute in the wake of his passing that split up his assets.

This is the story of the rise and fall of the Conway Twitty empire.

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Harold Lloyd Jenkins, who came to be known as Conway Twitty, was born on September 1st, 1933 in Friars Point, Mississippi right on the Mississippi River. He was named after the silent movie actor Harold Lloyd. Music and religion were big players in the Jenkins household. By the time he was twelve the family was living in Helena, Arkansas, and Twitty was already performing in a group called the Phillips County Ramblers. By his teenage years, he was preaching in church revivals. Impassioned and charismatic, Harold Jenkins showed a knack for holding a crowd in his hands no matter what he did.

Jenkins also showed promise as a baseball player and was recruited by the Philadelphia Phillies out of high school. But all of these passions were put on hold when he was drafted into the U.S. Army and served in the Far East. Harold played music when he could while in the armed services, including in a group called The Cimmarons. When he was discharged, the Phillies once again extended their offer to him to play baseball, but by that time Harold Lloyd Jenkins had caught Elvis Presley fever, and he headed to Memphis to become a rock n’ roll star.

In the mid ’50s when you wanted to be in rock n’ roll, Sun Studios and Sam Phillips is where you pointed your nose. That’s where Jenkins landed, but Phillips was focusing on performers singing rhythm and blues, which put Phillips at odds with Conway Twitty’s country and bluegrass influences. Jenkins did record for Sun, but no singles were ever released, except for the song “Rockhouse” that Jenkins wrote and Roy Orbison recorded.

Harold Jenkins did perform with Elvis and others on the Memphis club circuit at the time. In 1957, he officially adopted the name Conway Twitty at the suggestion of his manager Don Seat, who though he needed a name with more star power. The name is a combination of Conway, Arkansas, and Twitty, Texas—two names chosen off a map. For a moment, Conway thought he would record rock material under the new stage name, and his country material under Harold Jenkins, but ultimately decided to go with Conway all the way.

Conway Twitty did okay as a rock n’ roll performer, most notably landing the #1 hit song “It’s Only Make Believe” in 1958. Even though it was a rock n’ roll song, it was recorded in Nashville with country session players such as Grady Martin and Floyd Cramer, and Conway would later record the track as a country song as well. Though it was Conway’s big breakout, some attribute the song’s success to it sounding so similar to Elvis, audiences mistook it as a song from The King.

Conway also hit the Top 10 with the song “Danny Boy” and another called “Lonely Blue Boy” that Elvis recorded for the film King Creole. But with Conway’s religious background and his past dalliances with the priesthood, he became turned off with the behavior and attitudes of rock n’ roll fans. Perhaps this is a bit ironic considering some of the song he would record later as a country star. But during the middle of a 1965 performance in New Jersey, Conway Twitty walked out on the crowd and decided then and there to become a country performer. He moved to Oklahoma City instead of Nashville to set up his home base.

Conway Twitty signed with Decca Records in 1966 and started releasing country albums. Since many in Nashville knew Conway as a rock n’ roll and rockabilly guy, the reception was a little frosty at first. But once Conway landed a #1 song with “Next In Line” in 1968, the ice broke, and Twitty would assemble one of the greatest strings of hits in the history of country music. The songs “I Love You More Today” and “To See My Angel Cry” were other early hits. Then came Conway’s signature song “Hello Darlin'” in 1970, written by Conway himself. It was all over. Conway Twitty was a country music superstar.

Similar to his idol Elvis, Conway called upon sex appeal to create interest in his music. But since this was country, Twitty had to obfuscate the messages a bit more. It was these songs leveraging innuendo that undergirded his appeal. In 1973 when he released “You’ve Never Been This Far Before,” some disc jockeys refused to play it, considering it too suggestive. Though as is often the case, the controversy only fed interest in the song, and it still shot to #1, and for three straight weeks.

This sort of quiet bad boy persona that became Conway’s signature also worked so well though his collaborations with Loretta Lynn who personified the strong country woman who didn’t take any gruff from misbehaving men. Conway and Loretta set the standard for the country music duet, only rivaled by George Jones and Tammy Wynette. Conway and Loretta won the CMA Vocal Duo of the Year award every year between 1972 and 1975.

Along with the incredible amount of #1 songs Conway Twitty amassed, his longevity as a commercially viable country star is just as remarkable. When he landed the #2 song “Crazy in Love” in 1990, it marked Conway’s fourth decade of landing a #1 or #2 hit in country. In fact to go along with all of his #1’s, Conway also had 17 songs peak at #2 or #3. Conway Twitty defined popular country music for nearly 30 years.

By the early 1980’s, Conway Twitty had amassed a huge amount of wealth, and all the success he could imagine in show business. It was then that he set of to secure his legacy and set up his children from two separate marriages into perpetuity. Once again taking a page from the playbook of his hero Elvis, he decided to erect not just a stately home, but a tourist destination where fans could learn about his legacy even after he was gone. It was called Twitty City.

Postcard of Twitty City

Before Twitty City came about, Conway Twitty had already tried to secure his name and legacy in ways that stretched beyond music. In 1968 after he’d already logged a couple of #1 songs in country and rock n’ roll, Conway thought he would share another signature passion he had with the public, his legendary Twitty burger.

The Twitty Burger wasn’t just your average hamburger. It included a hamburger patty, two slices of bacon, an bun of course, and mayonnaise as the dressing. But what made the Twitty Burger special was the graham cracker-encrusted pineapple set right on top that made the Twitty Burger a delicacy in the fast food space. Not even Elvis Presley’s peanut butter and banana sandwich could hold a candle to it.

Conway Twitty believed so much in the Twitty Burger, he decided to open restaurants to serve it, and envisioned it from the start as a franchise, with locations all across the United States. Twitty even attracted some high profile investors from the world of country music to back his vision financially, including Merle Haggard, Sonny James, and songwriter Harlan Howard. Conway raised roughly $1 million from his famous country music friends and others as investment capital for the franchise.

But Twitty Burger was doomed from the beginning. Due to poor management, Twitty Burger was not around for very long, and was closed completely by May of 1971. “What I know about is how to make records and how to sing songs, and I’m not too good at anything else, and Twitty Burger is a prime example,” Twitty said.

But the legacy of Twitty Burger is still around today due to a landmark case Conway Twitty fought with the IRS, and won. The “beef” the IRS had with Conway Twitty and Twitty Burger had to do with the famous country singer writing off repayments to his investors on his 1973 and 1974 income taxes. In 1973, Twitty took a $93,000 business expense on his taxes, and in 1974, and additional $3,600. The problem the IRS found was these business expenses had to do with Twitty Burger, but were declared under Conway Twitty’s country music earnings.

When Twitty Burger went asunder, Conway decided that the only honorable thing to do was to pay all of his investors back, which he did. The $96,600 he wrote off on his taxes in 1973 and 1974 was part of those repayments. Twitty and his lawyers argued that if he didn’t repay his debts, it could be detrimental to Twitty’s reputation as a country music singer. That is why it should be permissible to be written off under his entertainment earnings. Remember, Conway was already on shaky ground with some in country music since he’d started on rock n’ roll.

“It was the morally right thing to do,” Twitty insisted. “They put their money in Conway Twitty, and Conway Twitty did it all wrong – that’s why I paid them back.”

The IRS disagreed, saying losses from Twitty Burger had nothing to do with country music. So the matter went to court in 1982. What was the result? Conway Twitty won. In 1983, the U.S. Tax court determined that the personal image of country music artists are vital to their careers, and that Conway was in the right to declare the losses to protect his personal reputation. Quotes from country music historians explaining the importance of character and honesty in country music were considered by the court in the case.

“We’re fighting over $100,000,” said William Whatley, Conway Twitty’s attorney at the time. “Conway could make that much money in the first three minutes of a concert. It’s the principal that counts.”

Though it’s only an interesting snippet of country music history, the case known officially as Jenkins vs. Commissioner is much more significant when it comes to tax matters. The case is still cited as relevant case law even today in how entertainers can declare business expenses on their taxes, and how reputation can factor into those decisions.

And this isn’t the only lasting contribution from the case. In an unprecedented move, the court, after deciding in favor of the country legend, rendered their ruling partly in a song called “Ode To Conway Twitty.” It goes:

Twitty Burger went belly up
But Conway remained true
He repaid his investors, one and all
It was the moral thing to do.

His fans would not have liked it
It could have hurt his fame
Had any investors sued him
Like Merle Haggard or Sonny James.

When it was time to file taxes
Conway thought what he would do
Was deduct those payments as a business expense
Under section one-sixty-two.

In order to allow these deductions
Goes the argument of the Commissioner
The payments must be ordinary and necessary
To a business of the petitioner.

Had Conway not repaid the investors
His career would have been under cloud,
Under the unique facts of this case
Held: The deductions are allowed.

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In 1984, when the IRS decided not to appeal the court’s decision, they responded in kind, saying:

Harold Jenkins and Conway Twitty
They are both the same
But one was born
The other achieved fame.

The man is talented
And has many a friend
They opened a restaurant
His name he did lend.

They are two different things
Making burgers and song
The business went sour
It didn’t take long.

He repaid his friends
Why did he act
Was it business or friendship
Which is fact?

Business the court held
It’s deductible they feel
We disagree with the answer
But, let’s not appeal.

Yes, the Jenkins vs. Commissioner case holds as tax law even today, but the legal outcome that would befall Conway’s Twitty City was not as advantageous for keeping the Conway Twitty legacy alive into the future.

Conway Twitty died unexpectedly of an abdominal aortic aneurysm on June 5th, 1993. He was 59 years old. The day before his passing he’d been performing in Branson, Missouri when he fell ill during the show. Twitty eventually collapsed on his tour bus, and the driver Bill Parks drove him to the Cox South Hospital in Springfield, Missouri where emergency surgery was performed. But doctors knew it was unlikely he would pull through, and the call was put out for his family to come to his side.

Completely by chance, when Conway Twitty arrived at the hospital in Springfield, Loretta Lynn was at the same hospital tending to her husband Doolittle who was suffering from complications with diabetes and was gravely ill himself.

“When they brought Conway in I couldn’t believe it,” Lynn told Ralph Emery in an interview some years later. “I just could not believe it. It was the worst thing I’ve ever been through really. I stayed with Dee (Conway’s wife) and I stayed with the band for a while, and then I’d run up to see Doo, and then I’d run back to sit with Dee. And then I’d run back to see how Doo was, because he was in real bad shape. They thought he was going to die any time. I was in bad shape myself.”

Also at the hospital with Conway Twitty’s third wife Dee were Conway’s adult children Michael, Joni, Kathy, and Jimmy. They were all there together about an hour before Conway died. Loretta Lynn was by Doolittle’s side when she heard the news.

What transpired in the aftermath of Conway Twitty’s death was one of the most tumultuous estate battles in country music history, with Conway’s $15 million-dollar estate, the fate of Twitty City, as well as the fate of all of Conway’s possessions and the control of his music becoming embroiled in the bitter legal battle that would drag on for 15 years.

Conway Twitty was married to Ellen Mathews between 1953 and 1954. The two had married due to Ellen’s pregnancy with son Michael, but the marriage didn’t last long after the birth. Conway married his second wife Mickey in 1956, and they stayed married until 1984 aside from briefly divorcing in 1970. This marriage is where Conway’s children Kathy, Joni, and Jimmy come from. Conway married his 36-year-old office secretary in 1987— Delores “Dee” Henry—but never amended his will after the marriage. This is what led to the estate conflict.

Conway Twitty’s will and testament left everything to his four children, and didn’t even mention Dee, who at the time had become a significant part of his music business, including accompanying him on tours, and helping to produce music. But Tennessee law required Dee to receive at least a third of Conway’s estate as his spouse, throwing the whole will into dispute, as well as the fate of Twitty City.

Twitty City was constructed as the private home for Conway Twitty, his family, and to secure his legacy for future generations. It included a house for Conway’s mother, a house for each of his four adult children, as well as a 24-room mansion for himself and his second wife Mickey. There were also elaborate gardens, an extensive gift shop, at at Christmas, one of the biggest Christmas light displays in the South.

Private residences at Twitty City for Conway’s family

The idea behind Twitty City is that family would be together forevermore, and even after Conway Twitty passed, it would live on as a testament to his legacy, and to house the artifacts of his life. Conway’s four children also worked there, running the gift shop, giving tours, and performing other duties for annual salaries.

“I built Twitty City because I wanted to have a place where my kids and I could always be close together, and they have homes right here,” Conway explained in an episode of ‘Lifestyles of the Rich and Famous’ from the 80’s. “I also wanted a first-class place for country music fans to come to when they come to Nashville, and get as close to an artist as they can get. A lot of my friends in this business said ‘Conway, you’ve lost your mind.’ And I can understand how they feel, but they haven’t been as close to this concept as I have. I have all the privacy I need right here at Twitty City. I can come out my door and get to my office which is only 100 yards away if I want to without anybody ever seeing me. Or if I want to be seen, I can.”

But this strange public/private nature of Twitty City is said to have been what led to trouble between Conway and his second wife Mickey. She didn’t want fans constantly around her home. Something else Conway’s friends and family point to that caused friction in his marrige and elsewhere was an incident in 1981 when the country singer slipped and fell on the steps of his tour bus, hitting his head violently. After the fall, apparently Twitty’s personality took a dramatic shift and he never acted the same afterwards, or like his true self. He would forget to finish sentences, or would pick up a TV remote thinking it was a telephone.

Conway’s children didn’t exactly approve of Conway’s marriage to the much younger Dee in 1987, but they learned to live with it when Conway was still alive. But after his death, the executors of Conway’s estate shut off the children from the regular salaries they were receiving from their father and Twitty City for doing various tasks around the complex. The executors also hired Dee to be a consultant for how to handle Conway’s musical affairs after his death since she already was so deep in his affairs, further isolating his family from the process.

Conway Twitty’s children then tried to remove the will’s executors, but the probate court struck the motion down. Frustrated by the court’s decision, Conway’s daughter Kathy then went to the local newspaper, The Tennessean, to tell her story about how the heirs of Conway Twitty were getting locked out of the process by Dee and the executors, and how Dee had made out with the $1.8 million home she shared with Conway, and another $900,000 in life insurance after Conway’s passing before getting her third of the estate.

After the newspaper report, the entire process boiled over with animosity between the respective parties. Angry about the article, Dee demanded that the entire estate be liquidated so it could be split up equitably between the respective parties. In June of 1994, a Tennessee probate court agreed, and ordered the full liquidation of the entire Conway Twitty estate, including Twitty City, all artifacts and memorabilia, musical instruments and trophies, even down to the family’s baby photos and love letters between Conway and his second wife Mickey.

Once again, the executors of the will hired Dee to be the party to catalog all of Conway Twitty’s assets and get them ready for sale. One day when Conway’s daughters Kathy and Joni witnessed Dee and others loading boxes into her trunk from the Twitty City office, they confronted Dee and the executors asking them what was going on. The situation turned heated, and a judge issued a restraining order, barring Conway’s heirs from the property.

Eventually, all of Conway’s children and his 81-year-old elderly mother were told they most move off the property by August of 1994. While still grieving the death of their father, and amid a bitter estate dispute, Conway’s children had to uproot themselves from homes they believed they would be in forever and together as a family, and find new places to live. Twitty’s mother passed away two months later, with Conway’s children claiming the stress contributed to her passing. The Twitty City property was ultimately sold for $3 million.

Then came the auctioning off of all of the estate items. “It was almost as hard as losing our dad again,” says Conway’s daughter Joni. “These things were a picture of his life. It was a hard day. It felt like daddy dying again.”

Conway Twitty’s second wife Mickey also showed up to the auction, and saw that love letters between her and Conway were part of the items on the auction block. Mickey is quoted as saying, “That’s my mail. How can they sell my mail?” Mickey then grabbed the love letters from behind glass partitions, but police at the auction forced Mickey to return them so they could be auctioned off. The auction of Conway Twitty items lasted three days, and ultimately netted about $1 million dollars. Conway Twitty’s physical legacy had officially become a diaspora.

Then in 1996, Dee and Conway’s children entered into another legal battle. At the time, Conway’s heirs were seeking the medical records for their father, in part to help understand why months after passing a life insurance physical exam and getting the all clear from doctors, he died suddenly of the abdominal aneurysm. Meanwhile, Dee wanted to disinter Conway’s body and cremate it. Part of Dee’s motivation was due to graffiti that appeared on Conway’s grave calling Dee a “bitch” for being so aggressive against Conway’s kids.

Dee may have been winning in court. But in the court of public opinion, Dee was losing demonstrably. The news of Dee’s intention to cremate Conway’s body only made that public perception worse. Amid public backlash against Dee for wanting to disinter Conway, she ultimately dropped her petition with the court for him to be cremated.

The final piece of the Conway Twitty estate to be settled was his intellectual property, namely the control of his music publishing, royalties, as well as his name and likeness rights. After Dee and Conway’s children couldn’t come to agreement on how to share the assets, Dee once again advocated for them to be auctioned and split equally. However, as opposed to auctioning them publicly, the court decided to hold a private auction between Dee and Conway’s children where they will bid between each other for control. Pooling their money from their father’s estate, Conway Twitty’s children eventually cast the winning bid for control over his intellectual property, paying $4.2 million dollars.

Ultimately, the fight over the Conway Twitty Estate by his heirs results in Conway’s daughters Joni and Kathy testifying in front of the Tennessee State legislature about changing the law in the state that immediately rewards the spouse of a deceased individual a third of their estate. Due to the public backlash against what happened to Conway Twitty’s children, the Tennessee Legislature passed what is now known as the Conway Twitty Amendment to the existing state law.

The new amendment takes into account the duration of a marriage in estate proceedings. After Joni and Kathy told the story of what had happened with their father’s estate and Twitty City, lawmakers were reportedly crying, and hugged the two women afterwards, appalled about what had happened.

The law had been changed, but the damage had been done to the Conway Twitty estate, Twitty City, and the memorabilia that told the story of Conway Twitty’s life and career in country music.

As country music journalist and historian Robert Oermann says, “I think the unfortunate thing about the estate battle is that it has in a sense prevented carrying his legacy forward. Because the estate was frozen as it was for so long, it made people kind of forget a little bit, because he wasn’t being brought before the public.”

For the record, Robert Oermann also believes that Dee has gotten a raw deal from the public over the years, that she worked hard to promote Conway’s music in life and after his death, and was put in a difficult situation with the family.

The Trinity Broadcasting Network is who purchased the Twitty City complex itself, turning it into studios and offices for the television company, later calling it Trinity Music City. For some years after, tours of the grounds were still given upon occasion, and tourists could also still request to see Conway’s 24-room mansion. But as Saving Country Music reported in 2016, management finally ceased giving tours of the property.

Conway Twitty’s house

By 2023, the Conway Twitty home had fallen into disrepair since Trinity Broadcasting wasn’t using it, and had no incentive to maintain it. Then on December 9th, 2023, and EF-2 tornado ripped through the property, further damaging the home. Trinity declared the structure was beyond repair, and planned to demolish it to make room for new improvements on the property. But after a public outcry, In January of 2024, Trinity Broadcasting decided they would restore the home as opposed to demolish it.

Nonetheless, the Conway Twitty legacy in country music still feels like it doesn’t rest in its proper standing. It took until 2021 for many of his previously-unavailable albums to finally be reissued. But the numbers and legacy don’t lie. Conway Twitty was one of the most successful and beloved country music artists of all time.


Wilbur Cross: “The Conway Twitty Story: An Authorized Biography

Reality TV: “The Will: Family Secrets Revealed” – S02 – EP03

Saving Country Music: “Conway Twitty’s Former Twitty City No Longer Giving Tours

WKRN News 2 – “Conway Twitty’s Hendersonville Home Saved from Demolition

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