Classic Country Mysteries That Remain Unsolved To This Day

No one can sing a mournful ballad better than a classic country star. Those performers really made you feel their pain, expressing all the suffering they put into their songs. And while thankfully most country songs are just creations of a talented lyricist, unfortunately, many of the people who sang them had lived through horrors, or would come to bad ends. Classic country music was rife with tragic events.

The silver lining, if you are really looking for one, is that at least most of the biggest tragedies that befell classic country stars had obvious culprits. In most cases of terrible events like accidents or murders, assault or arson, someone was arrested, or at least what happened is pretty obvious. But every now and then something big and terrible went unsolved. Sometimes it might be just rumors that things weren't as they seemed, all the way up to an unexplained disappearance that has baffled authorities for decades, or a suspicious death, or even just a seemingly inexplicable incident the artist never bothered to give a reason for that has driven fans crazy looking for an explanation ever since.

Some of these mysteries might still have a chance of being solved, at least while the participants are still alive, while others you'll just have to accept you are never going to know the answer to. But for anyone who loves classic country, true crime, or just a good brainteaser, these are the mysteries that remain unsolved to this day.

Why did Jim Sullivan disappear?

Jim Sullivan was a country-blues musician with an edge of psychedelic, according to the New York Times. He had famous friends including actor Dennis Hopper and had released two albums. Then he disappeared and was never seen again.

Jim had a family but left them behind to go to Nashville for work. Except he never showed up. His wife Barbara got a call from him on March 5, 1975, the day after he left California. He started by telling her he was fine, always something terrifying to hear when you have no reason to think the person saying it is not fine. Despite asking him to tell her what was wrong, he refused. "You wouldn't believe if I told you," he said, she recorded later. "Forget it. Just forget I said anything." That was their last phone call.

Jim's car was found abandoned three days later in the small town of Santa Rosa, New Mexico. It contained his ID, a box of his albums, and his beloved guitar. "When I heard that, I knew he wasn't coming back," Jim's friend Al Dobbs said. "No matter what, Jim would never have left his guitar." The police investigation turned up no clues about where Jim was or why he'd disappeared. One local thought they didn't do a great job though, saying, "I always thought there was something strange about how that went down, why they didn't investigate it more." A search by family members and volunteers was more thorough. "There was no arroyo left unturned," another local said, "and no trace of him found."

Was Tammy Wynette really kidnapped?

In 1978, the "First Lady of Country Music" Tammy Wynette told People magazine about the terrifying carjacking and kidnapping she'd been the victim of a few weeks before. "I felt a poke in my side and heard a man's voice say, 'Drive!'" she recounted (via The Boot). "All I could see was a brown glove, a lot of hair on his arm and two inches of gun barrel ... It was the most terrifying experience of my life." Wynette was finally released 80 miles away and went for help. She had visible injuries on her face and neck where the kidnapper had punched, slapped, and strangled her.

But did those injuries really come from a kidnapper? Did a kidnapping even take place? There is a lot of reason to doubt Wynette's story. Instead, her children contend she was in an abusive marriage and the injuries were caused by her husband, their stepfather George Richey. In her memoir (via The Boot), Tamala Georgette Jones wrote, "She did admit to my sister that when all that stuff came out about her being kidnapped in 1978 that she and Richey had had a fight and he had beaten her. He threatened to destroy her life and write a tell-all book so she decided to stay with him ... so he concocted the kidnapping story for PR." Richey called previous accusations by Jones "preposterous," and, publicly, Wynette never recanted her kidnapping story.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

When (and where) did Hank Williams die?

Hank Williams Sr. is one of the most famous country music stars of all time, despite dying at 29. The weird thing is no one really knows when Hank Williams died. According to the Atlanta Journal-Constitution, on New Year's Eve 1952, a 17-year-old Charles Carr was driving Williams 500 miles to get to a gig the next day. Officially, he realized something was wrong with his passenger in the back seat in the early hours of the morning and detoured to a hospital. Williams was pronounced dead there, with January 1, 1953 appearing on his death certificate.

But there are plenty of people who have other ideas about when Williams breathed his last, possibly even hours before. Knox News reports that Tennessee Highway Patrol Cpl. Swan Kitts pulled Carr over at 1 AM that morning for driving erratically and saw Williams in the back seat. He reported the musician already "looked dead" but was reassured by Carr that Williams was just under the power of a sedative.

Could those injections of morphine, given to him at a Knoxville hotel before getting back on the road, have been what killed him? The doctor who gave them obviously disagreed, saying, "The shots I gave Williams had absolutely nothing to do with his death. It is ridiculous to think that they did." But sometime after receiving the injections, Williams had to be brought to the car in a wheelchair. Some think he was already dead at that point, and his corpse was put in the car by people who thought he was just out of it.

Who killed Curley Shelton?

Proving that being a lead singer is sexy no matter what, William "Curley" Shelton of the band Dixie Six – stars of the 1950s TV music program "Hillside Hoedown"– who was described by the Courier and Press as looking like "the miracle offspring of Elvis Presley and Andy Griffith," was nevertheless a confirmed ladies' man. "[Curley] was something else," a local bar owner said. "He sang those old love ballads, and women just went crazy. He had no trouble getting all the women he wanted."

This would become a problem for the musician. Shelton once flagged down the then-Henderson County Sheriff Lee Williams and told him that a guy "is after me and wants to kill me. What can I do?" "Why is the man after you?" Williams said he asked. The answer? "Because I been with his wife a bunch of times." The sheriff told him to leave the man's wife alone.

Three years after that conversation, on December 5, 1957, Shelton was found in his car outside a VFW hall. He'd been beaten to death, pummeled so badly that the cops who arrived on the scene mistakenly thought he'd been shot in the head. Despite an extensive investigation where over 100 people were questioned, no one was ever arrested, let alone convicted for the murder. But the sheriff claimed to know what the motive would have been. "Shelton was caught with a woman by a man – maybe the woman's husband – and the man simply beat him to death," Williams said. "That's my theory, and I'm sticking to it."

Who were the Weems String Band and what happened to them?

There's only one known photo of the Weems String Band, and you are looking at it. They appeared literally out of nowhere and disappeared right after. During the 1920s, "hillbilly string band" music was all the rage, and the Weems String Band recorded a single record for Columbia – yet "R. Crumb's Heroes of Blues, Jazz, and Country" explains that their album "is considered by many to be the single finest white traditional recording of the period."

Their playing style made the band even more mysterious. Despite living in "the backcountry of Perry County, Tennessee," they held and played their instruments in distinctive ways that indicated they almost certainly had professional training on the violin, which seems impossible for people who came from somewhere so remote. Plus, one of the members played the cello, which you normally wouldn't find in a string band at all. And they didn't play in the normal style either, instead producing what was essentially an experimental record at a time no one in the genre was doing anything like that. "R. Crumb's" goes so far as to say that "no group equaled the brilliant creativity of the Weems String Band."

The record they produced had an A-side, "Greenback Dollar," and a B-side. That was all these virtuosos ever recorded. While there are six people in the photo, we only know who four of them were: Dick, Frank, and Jesse Weems, and their brother-in-law Alvin Condor. The other two are thought to be younger Weems brothers, but their names were lost to history until a member of the forum, Banjo Hangout, offered that the two were Atlas "Dodge" Conder and Ray Hinson. The explanation was anecdotal, so whether or not there's truth to it is up to folk tradition. 

What did Billie Joe throw off the bridge?

Classic Country Music calls Bobbie Gentry "one of the most mysterious figures in country music history." After a decade of country music success, she decided that performing had lost its attraction and went back to a normal life. She hasn't done a public appearance since 1981.

But she left a mystery in song behind her that's been driving fans crazy ever since. "Ode To Billie Joe" tells the story of a girl who finds out at dinner with her family that the titular Billie Joe has completed suicide by jumping off the Tallahatchie Bridge. It's implied that she and Billie Joe were sweet on each other and — here is the mystery — they had been witnessed throwing something into the river below that same bridge shortly before he died. What did they throw? We never find out.

Explaining her reasoning for keeping the detail so vague, Gentry said, "First, it locks up a definite relationship between Billie Joe and the girl telling the story, the girl at the table. Second, the fact that Billie Joe was seen throwing something off the bridge — no matter what it was — provides a possible motivation as to why he jumped off the bridge the next day." As for what they threw in? Gentry has never told, although she was asked all the time by fans and heard many theories. (Engagement ring? Draft card? Baby?) She once commented, "Suppose it was a wedding ring."

A TV movie based on the song gave its own answer that really disappointed fans: the girl's childhood doll.

What was Jim Reeves' connection to the Kennedy assassination?

Country star Jim Reeves had a weird connection to the Kennedy assassination, made weirder by the fact he died in a plane crash less than a year later. Larry Jordan's biography "Jim Reeves: His Untold Story" records a Texas radio station owner's account of what happened as news of the assassination unfolded in November 1963 and Lee Harvey Oswald's picture was shown on TV: "Reeves told me and everyone else watching that he recognized Oswald and had remembered seeing him at the Longhorn Ballroom in the crowd on several occasions." It's also alleged that Reeves knew Jack Ruby from the same place, where Reeves and his band often performed.

In August the next year, Reeves was killed in a small private plane crash. But he had something mysterious on him. Songwriter John Loudermilk recounted how "[Music producer Chet Atkins] called me and he said, 'Jim's down. He crashed last night and we need to go out and find him.' And I said, 'Why?' And he said, 'He's got a briefcase that has some important papers in it that are private, and nobody should have those.'" The briefcase was never found.

All a coincidence? Possible, but the mystery deepened. Larry Jordan, Reeves' biographer, says that while researching his book "I received an unsolicited phone call from a man ... who supposedly had worked for U.S. intelligence – who warned me not to probe too deeply into the Reeves crash." As with so many things surrounding the JFK assassination, conspiracy theorists see something fishy going on when you add it all together.

Why did Charlie Rich burn an envelope when presenting at the CMAs?

Charlie Rich had a 35-year career, according to History, which included 11 No. 1 records on the country charts, and even a crossover hit that reached No. 1 on the pop charts. And in 1974, the Country Music Association of America awarded him Entertainer of the Year, the group's biggest accolade. This meant that he would present that same award the following year, but this is when his career went up in flames, literally.

Rich took the stage to announce the winner, opened the envelope, and read out "John Denver." But then Rich did something inexplicable. He took a step back and fished in his pocket for a lighter. Then he lit the envelope on fire. Fortunately, John Denver wasn't there to see this, but those who were in the audience were gobsmacked.

What was Charlie Rich trying to say? Since Rich never explained himself, it's been left to others to try to theorize about his mysterious action (which, incidentally, got him banned from all future CMA award shows.) Many people think he was mad about Denver's win, possibly because he didn't think Denver was really a country musician. But Rich himself was often considered "not country enough." There's also the fact Rich admits he was on prescription pain medication washed down with multiple gin-and-tonics at the time. His son has his own reasoning: "He used bad judgment. He was human after all. I know the last thing my father would have wanted to do was set himself up as judge of another musician."

Where is the head of the woman who haunts Bobby MacKey's Music World?

Bobby MacKey's Music World (pictured) is a popular honkey-tonk in Kentucky, owned by the eponymous country singer Bobby MacKey. There's a sign on the door reading "Warning to our Patrons: This establishment is purported to be haunted. Management is NOT responsible and cannot be held liable for any actions of any ghosts/spirits on these premises" (via The Bitter Southerner). The honkey-tonk has appeared on many ghost hunting shows, and is purported to be the site of many grisly crimes over the years, according to the Travel Channel. Almost all of it is legend, but one horrific crime did take place nearby, and the victim is said to be one of the ghosts that haunt the building today.

In 1896, the 5-months-pregnant Pearl Bryan arrived in Cincinnati, Ohio in order to procure an abortion. The father of her child and his roommate were waiting for her at the train station. What happened next is a mystery, but somehow Bryan ended up dead. When her body was found, it was missing a head. Before they were executed for her murder, the men changed their story about what they did with Bryan's head numerous times, saying it was "in the Ohio River," "buried in a sandbar at Dayton, Kentucky," and "burned in a furnace." Despite extensive searches, the head was never found.

One legend says the men threw it into the already-bloody well of a nearby slaughterhouse, across the river in Kentucky. The building that housed the slaughterhouse? It's now the home of Bobby MacKey's.