The Bad Boys Of Outlaw Country

For many people, the first country outlaw artists were Willie Nelson, Waylon Jennings, and Bobby Bare. According to Pitchfork, the "outlaw" name was first coined by Hazel Smith, a country music insider at Tompall Glaser's legendary Hillbilly Central music studio. While most people think that outlaw country refers to a singular type of country music sound, it really describes a lifestyle and attitude more than anything.

For many people, the outlaw country ethos means doing things your own way and fighting against "the man" and society, sometimes with questionable and dubious legality. It's also an internal rebellion against the glitter and pomp of mainstream pop country, instead extolling the virtues of a more simple life, dedicated to personal passions rather than commercialized and manufactured fads.

The genre truly began in the early-1970s, when Bare started to earn the right to dictate what he wanted to play and who wanted to play with. At the same time, Nelson had headed home to Austin, Texas, and he, along with Jennings and Kris Kristofferson, began to popularize the now-famous outlaw country sounds. However, the outlaw country scene was bound to be short-lived, and after a few landmark albums progenitors like Nelson and Jennings moved on to new passages. The spirit of outlaw country still lives on today, but by 1978 the original scene was deteriorating, and by 1979 it was dead.

One of the biggest names in all of country music, Merle Haggard was also a significant contributor to the outlaw country scene. As The New York Times reported in their obituary of him, Haggard drew upon his rough and tumble upbringing as material for his incredibly powerful lyrics. Initially raised in an abandoned train boxcar-turned-house, he was just nine years old when his father died and left him in the care of only his mother.

His adolescent and teenage years were littered with arrests for stealing and other petty crimes, and in 1957 he found himself in San Quentin Prison on burglary charges. It was at San Quentin that he started his writing career, and within a few years, he was out on parole. He truly exemplified the outlaw country ethos and lifestyle, living by the skin of his teeth and breaking the law to make ends meet. Though he would later play alongside him, Haggard was actually still a prisoner when Johnny Cash played his original San Quentin concert in 1959 (via GQ).

Even though he was making music and no longer incarcerated or constantly on the run from the law, Haggard never got rid of his rebellious personality and mindset. He still found himself in jail a few more times during his career, which was also punctuated with five marriages — all of them ending in divorce, but he always made music on his own terms, like a true outlaw.

While her name might not be the first that comes to mind when you think of outlaw country, Emmylou Harris is definitely an outlaw in her own right. Born in 1947 in Birmingham, Alabama, Harris began performing music while a student at the University of North Carolina (via the Alabama Music Hall of Fame). Though she started out mainly being influenced by the folk and psychedelic movements of the 1960s, in the early 1970s she was introduced to country music, and the arc of her career profoundly changed.

She began putting out records with covers of famous country songs and with collaborations with country music stars. She covered outlaws like Merle Haggard and played with outlaws like Willie Nelson. Musically, she was always willing to be a risk taker, playing the type of music that she wanted, regardless of whether it was always commercially successful — the true ethos of a country outlaw. 

In 2022, in light of her outlaw bona fides, she was brought on to be a part of the 6th Outlaw Country Cruise (via Rolling Stone). She is one of the few women to make a name for herself in the outlaw movement, and she is definitely a musical force to be reckoned with. 

Another one of the true country outlaws along with Willie Nelson, you absolutely cannot tell the tale of the outlaw movement without talking about the late Waylon Jennings. As he and Robby Turner explained in "Highwaymen: Friends Till The End" (via PBS), Jennings and Nelson were the true founders and architects of the country outlaw movement. They made the decision to forge their own paths by writing and releasing the kind of music they wanted, without any added fluff or overproducing from the record companies.

Jennings' 1974 album "This Time" was one of the first examples of the country outlaw ethos and lifestyle that shook the country music establishment. Two years later, in 1976, he released "Wanted: The Outlaws" with Nelson and his wife at the time Jessi Colter, which saw incredible commercial success and firmly established the movement as part of the country mainstream (according to The New York Times).

Like other country outlaws, he struggled at times with substance abuse during his career, but he produced an incredible breadth of work. During his career, he was part of five-dozen albums and was responsible for selling over 40 million records, and was part of the supergroup The Highwaymen, which featured pal Nelson, as well as fellow outlaws Johnny Cash and Kris Kristofferson. He died a premature death in 2002 at the age of 64 due to natural causes, but will always be remembered as the true country outlaw.

Considering he was one of the most important and consistent parts of the American country music scene for several decades, it's of little surprise that Johnny Cash was also a big part of the outlaw country movement and another of its elder statesmen. One of his earliest songs, "Folsom Prison Blues" from 1954, described the life of an incarcerated outlaw and was an early look at what the genre would eventually morph into a few decades later (via The New York Times). His nickname was "The Man in Black," and his mysterious and gruff demeanor put him right at home with other outlaw greats.

He is credited with helping to popularize the outlaw movement, using his stature to make it acceptable to those in the Nashville establishment. In the 1980s, Cash joined up with other outlaws Willie Nelson, Waylon Jennings, and Kris Kristofferson to form the outlaw supergroup The Highwaymen.

In the late-1960s, just before the outlaw movement kicked off, Cash was putting out his live albums from the Folsom and San Quentin prisons, and though he wasn't putting out outlaw albums at the height of the movement, his persona and image have always been that of a country outlaw. Cash died in 2003 at the age of 71 of natural causes.

Kris Kristofferson is another one of the biggest names in outlaw country. Born in 1936 in Texas, the home of outlaw country, Kristofferson is the rare outlaw to have pursued both a Rhodes Scholarship and master's degree before starting his country career (via Britannica). His big break was at the 1969 Newport Folk Festival, which happened just after his introduction to fellow outlaw Johnny Cash. He was one of the earliest performers in the outlaw country genre (via Pitchfork).

By the mid-1970s, Kristofferson not only had a burgeoning music career but was also becoming an accomplished actor. In 1973, he starred in "Pat Garrett and Billy the Kid," playing the title character of Billy — a real-life outlaw. He won a Grammy in 1971 and soon became a part of the outlaw country movement. In the 1980s, he formed The Highwaymen with Cash, Willie Nelson, and Waylon Jennings. In recognition of his talent, he has been inducted into the Songwriter Hall of Fame and was given a Grammy Lifetime Achievement award.

Not your typical outlaw, Kristofferson did not have documented struggles with substance abuse or misogyny, and never found himself on the wrong end of the law dealing with lengthy jail or prison stints. He was actually an Army Ranger in the 1960s, marking him as a truly unique, but thoroughly patriotic and American, country outlaw.

Billy Joe Shaver never got the respect or name recognition as outlaws like Willie Nelson and Waylon Jennings, but he was still every bit responsible for creating and nurturing the movement during its early years (according to The New York Times). In addition to writing songs for outlaws, Shaver also recorded his own music, and first became popular after appearing on Jennings' 1973 album "Honky Tonk Heroes." He helped Jennings write nearly all of the songs, and his first album was produced by outlaw Kris Kristofferson.

Another native of Texas, Shaver started trying his hand at being a professional musician in the 1960s but didn't see success until the outlaw movement kicked off in the early-1970s. He suffered personal struggles, including the deaths of his wife and daughter, and in 2004 was the subject of a documentary, "The Portrait of Billy Joe."

Shaver died in 2020 at the age of 81 due to natural causes. He passed away less than a week after fellow outlaw Jerry Jeff Walker, in Waco, Texas, near his original home of Corsicana.