“Outlaw” is a term that’s been bandied around quite a bit in the field of country music. What started out as more or less a marketing campaign, culminating in the 1976 Wanted: The Outlaws compilation album, the term “Outlaw” originally applied to the era’s country music singers who rejected the mainstream and pursued their own sounds and aesthetics, Nashville record executives be damned.
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Waylon, Willie, and Kristofferson are a few of the names most associated with the Outlaw country movement. But the “Outlaw” label surely rankled for those in Music City who really had served time, and would rather leave their past behind—until it came time to cash in, that is.
A handful of notable country icons have faced DUIs and drug charges—Hank Williams, Johnny Cash, George Jones, and, yes, Waylon Jennings. But here are three legendary country singers who served significant prison time for serious crimes.
Merle Haggard
By far the highest profile of the bunch, Merle Haggard was also the most reformed by his carceral experiences. Going on to have one of the longest and most artistically fruitful careers the world of country music has ever seen, Haggard started out as a chronic truant and juvenile delinquent, who not many would have bet on to ever amount to much.
As Haggard told Terry Gross in their 1995 conversation for Fresh Air, “I was really kind of a screw-up… I spent […] seven years running off from places. I think I escaped 17 times from different institutions in California.”
The young Haggard had already developed a fine singing voice by young adulthood, attracting the attention of Lefty Frizell at one legendary engagement, resulting in an invitation to perform onstage with his idol. But money troubles led him back down the outlaw path, and after a botched armed robbery in his native Bakersfield, he was sentenced to hard time in San Quentin Federal Penitentiary.
Haggard may have been a “screw-up” initially, but he was destined for something greater. Legend has it that, after seeing Johnny Cash’s 1960 performance at San Quentin, Haggard knew he had to follow his dreams and pursue a career in music. Upon his release, he quickly gained notoriety for his talent, and the rest was history.
And I turned twenty-one in prison doin’ life without parole
No one could steer me right but Mama tried, Mama tried
Mama tried to raise me better, but her pleading, I denied
That leaves only me to blame ’cause Mama tried
Johnny Paycheck
Johnny Paycheck is a sad example of a generational talent who was constantly set back by his own demons, plagued by substance abuse and (what are now called) mental health problems that made it difficult for him to thrive in the music business, despite possessing preternatural levels of musical ability.
Paycheck, born Donald Lytle, walked the line between child prodigy and problem child from the start. According to his obituary, Paycheck was a professional musician by age 15, before joining the Navy. His service was plagued by behavioral problems, culminating in a court-martial and two years’ imprisonment for assaulting an officer.
Upon his release, he moved to Nashville, where his tenacity, instrumental chops, and vocal similarity to George Jones got him a job as one of the Jones boys. He soon went solo as Johnny Paycheck, and years of hit records (and hell-raising) ensued.
But, unlike Haggard, Paycheck’s legal troubles didn’t end with career success—in fact, far from it. In 1985, Paycheck spent 22 months in an Ohio prison for shooting a man in a bar (thankfully, the bullet only grazed the man’s head). He was pardoned by Ohio’s governor and released. Paycheck then more or less settled into the role of a country music elder statesman, by and large avoiding any major trouble after his release (except with the IRS).
When they put them handcuffs on me, Lord how I fought to resist
But agent clamped ’em tighter, ’til that metal bit into my wrist
They took my belt and my billfold, my fingerprints, and the profile of my face
And then they locked away the only hell my mama ever ever raised
David Allan Coe
Similarly to Haggard, Outlaw country singer David Allan Coe was a juvenile delinquent who mostly grew up in correctional institutions before graduating to, well, prison.
According to a 2005 Rolling Stone article, it was in prison that Coe received encouragement to pursue music from none other than blues shouter Screamin’ Jay Hawkins. Never one to shy away from a good publicity stunt, Coe’s first album, Penitentiary Blues, was practically a whole record of prison songs, including such titles as “Cell #33,” “Death Row,” and “Oh Warden.”
The album, which skewed more blues than country, went largely unnoticed in Nashville at the time of its release. Coe would later re-brand as a country singer, however, and with his third album The Mysterious Rhinestone Cowboy, it was clear that he was all in.
Coe’s smirking, humorous (if at times ribald or even outright offensive) brand of country music was a natural fit for the Outlaw movement, and such tunes as “You Never Even Called Me by My Name” and “Longhaired Redneck” simultaneously mocked and embraced Music City and its denizens.
Coe was also at one time a member of the Outlaws Motorcycle Club. Now, if that ain’t outlaw…
The loudmouth in the corners gettin’ to me
Talkin ’bout my earrings and my hair.
I guess he ain’t read the signs that say I’ve been to prison,
But someone ought to warn him
Before I knock him off his chair.
Photo by Beth Gwinn/Getty Images
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