No one wants to wind up in prison, but several country artists have had big hits about being in jail. We found four country songs about being in prison, songs that became big hits at country radio.
Videos by American Songwriter
“Ol’ Red” by Blake Shelton
“Ol’ Red” is one of Shelton’s biggest songs of his entire career. Written by James “Bo” Bohon, Don Goodman, and Mark Sherrill, the song was first recorded by George Jones, and then by Kenny Rogers, before Shelton recorded it. “Ol’ Red” is on Shelton’s eponymous debut record.
The song says begins with, “Well, I caught my wife with another man / And it cost me ninety-nine / On a prison farm in Georgia / Close to the Florida line / Well, I’ve been here for two long years / I finally made the warden my friend / And so he sentenced me to a life of ease / Takin’ care of Ol’ Red.”
“It’s so strange to me that was the very first song I ever found accidentally when I moved to Nashville,” Shelton says (via Songfacts). “I held onto it for many, many years and had to fight to get it on my album. Once I got it on my album, I had to fight to get it released as a single. Then it was another battle to get them to put it out as a video.”
“Mama Tried” by Merle Haggard
Merle Haggard wrote “Mama Tried” by himself, releasing it in 1968 with the Strangers. The song is about a man who finds himself in prison, in spite of his mother’s best intentions to teach him right from wrong.
“And I turned twenty-one in prison doing life without parole,” Haggard sings. “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.”
“By the time I was 20 years old, I was in San Quentin,” Haggard says. “’Mama Tried’ is probably a child of all that. The song says I’m the ‘one and old rebel child.’ I did have two older siblings, but they were excellent citizens, never went to jail. I was the one and only rebel.”
“Folsom Prison Blues” by Johnny Cash
Johnny Cash first released “Folsom Prison Blues” in 1955. In 1968, he released a live version of the song from Folsom Prison. Cash was inspired to write the song after seeing the film Inside the Walls of Folsom Prison.
“When I was just a baby, my mama told me, / ‘Son, always be a good boy, don’t ever play with guns,’” Cash sings. “But I shot a man in Reno just to watch him die / When I hear that whistle blowin’, I hang my head and cry.“
“Behind Bars” by Jelly Roll With Brantley Gilbert and Struggle Jennings
Jelly Roll knows a thing or two about being in jail. Jelly Roll spent a lot of his formative years in prison, first for minor offenses. Later, he was charged with a felony when he was still a teenager. He includes “Behind Bars”, a song he sings with Brantley Gilbert and Struggle Jennings, on his 2023 Whitsitt Chapel album. The song reflects on what life is like both in and out of jail.
“Behind Bars” says, “Jack’s got a rap sheet a country mile long / We’re thick as thieves, but he’ll leave me still drunk waking up on the neighbor’s lawn / Jose’s got a death wish, we’ve had some crazy nights / But he’s been with me since about ’03, you could say we’re doing life.”
Photo by Rusty Russell/Getty Images
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