5 True Stories of Outlaw Country Artists Being Outlaws

Waylon Jennings greets First Lady Rosalynn Carter, Library of Congress

Outlaw country stars used to have some teeth.

The term outlaw is used in modern country more like it’s a flavor of Doritos rather than a statement of character. But that wasn’t always the case. The legendary outlaw country artists were, well, outlaws.

They operated outside the Nashville machine. They played in prisons. Some were ex-cons. One of them even shot a guy in the face (it was self-defense.) Yeah, they were a rowdy bunch.

Here are five wild stories about the country stars of yesteryear.

5. Kris Kristofferson lands a helicopter on Johnny Cash’s lawn to give him a demo.

Screengrab via YouTube
Screengrab via YouTube

Kris Kristofferson is one of the most dynamic figures in country music. Before he became a country star, he was a Rhodes Scholar, an Army Captain and even a helicopter pilot. But his passion was always music. Despite pressure from his family to choose a different path, Kristofferson chose to pursue his musical dreams.

In the late 60’s, he took a job as a custodian at Columbia Records in Nashville so he could be close to the artists he admired, guys like Bob Dylan and Johnny Cash. At the time, Kristofferson had written a number of songs, and he wanted Cash to hear one in particular. He was so eager to get the song into Cash’s hands that Kristofferson convinced his buddy to lend him a helicopter so that he could fly to Cash’s estate and deliver the song in person.

There are two versions of what happened next. One says Kristofferson touched down in Cash’s front yard with the tapes and handed them to Cash, asking him to listen to the song. The other one claims Cash wasn’t home. Either way, Kristofferson’s brash move got “Sunday Morning Coming Down” in Cash’s hands, and the song became one of Cash’s biggest hits.

4. Billy Joe Shaver shoots a man in the face in self-defense 


I’m not condoning murder or idolizing a man for shooting another man in the face, but this story certainly added to Billy Joe Shaver’s outlaw identity.

In 2007, Shaver was leaving a bar outside Waco, Texas when a man approached him looking for a fight. One thing led to another – you know how that goes – and Shaver drew his gun and shot him down.

The country star later went to court, and in 2010 was found not guilty. During the trial, one witness claimed that Shaver asked the man “Where do you want it?”, but that bit was later discredited (It did, however, become the title of a Dale Watson song.) When approached by reporters outside the courthouse, Shaver said, “I’m very sorry about the incident. Hopefully, things will work out where we become friends enough so that he gives me back my bullet.” Damn.

Shaver later wrote a self-referential song about the event titled “Wacko from Waco.”

3. George Jones Rides His Lawnmower to the Liquor Store 

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It’s no secret that “No Show Jones” had a notorious thirst for booze. George Jones’ penchant for drinking once inspired him to use a creative form of travel to get to the liquor store.

In 1966, Jones used to live in Beaumont, Texas with his former wife Shirley Corley. She once became so frustrated with Jones’ frequent drinking that she hid his car keys so that he couldn’t drive to the liquor store eight miles away. But that didn’t stop him. Deciding that it was too far to walk, Jones found the keys to his lawnmower and rode that instead.

He later described the incident in his memoirs: “There, gleaming in the glow, was that 10-horsepower rotary engine under a seat. A key glistening in the ignition. I imagine the top speed for that old mower was five miles per hour. It might have taken an hour and a half or more for me to get to the liquor store, but get there I did.”

The incident would later become a running joke throughout Jones career. Two country music videos — “One More Last Chance” by Vince Gill and “All My Rowdy Friends Are Coming Over Tonight” by Hank Williams, Jr. — have featured Jones riding his tractor. Go Possum, go!

2. Johnny Cash plays Folsom Prison


Johnny Cash was a man of the people, both upstanding citizens and convicts alike. In 1955, Cash recorded “Folsom Prison Blues”. Inspired by the song, Cash spent the next decade pondering the idea of performing in a prison. For years, the execs at Columbia Records wouldn’t let him do it, but when management changed, the opportunity opened.

In 1967, Cash got his wish and recorded the iconic album At Folsom Prison, which would be released the following year. On the record, you can hear Cash interact with the prisoners as if he’s one of them. At one point, he was so fired up that he flipped off the warden’s cameraman.

That image, pictured above, is perhaps the most iconic photo of Johnny Cash, because it embodies the outlaw spirit of his younger years. It’s also somewhat ironic in today’s world, because while it so blatantly defies the “man”, it’s been printed and sold on t-shirts and posters across the world, making millions for corporate schlubs.

1. Willie Nelson leaves Nashville for Austin

Kris Kristofferson, left, Willie Nelson, center, Waylon Jennings, right
Kris Kristofferson, left, Willie Nelson, center, Waylon Jennings, right

In the 1960’s, Willie Nelson was considered one of the best songwriters in Nashville, penning hits for greats like Ray Price and Patsy Cline. Nelson was also a great performer in his own right but didn’t fit in with the standards of the music industry.

Fed up with the system of his day for many of the same reasons artists get frustrated today, Nelson packed up and headed back to his home state of Texas, settling in Austin. In Texas, Nelson could be himself, and he quickly gained a strong and devoted following by cultivating his own brand of country, which brought together the cowboys and the hippies.

Nelson’s efforts and his music and the music of his contemporaries were instrumental in the development of outlaw country and the Texas country music, which is uniquely different from what’s happening in Nashville.

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5 True Stories of Outlaw Country Artists Being Outlaws