From Inmates to Icons: 3 Artists Who Spent Time In Prison

For as long as music has been around, one of the most-used archetypes has been that of the outlaw—musicians who’ve embraced being symbols of defiance and rebellion. While most have never actually run afoul of the law, there are artists who have served prison time and then used these profound experiences to inform their music. Here are three artists who did just that, and became icons because of it.

Merle Haggard

Imprisoned at San Quentin when Johnny Cash made his famous concert appearance there. Haggard was incarcerated after a failed escape attempt from a county jail following a conviction on an armed robbery charge. Haggard, who is often associated with the outlaw country movement, sings his prison tunes as a testament, not a sales pitch.

So I do life in prison for the wrongs I’ve done / But I pray every night for death to come / My life will be a burden every day / If I could die, my pain might go away. Through these lyrics from the chorus of his 1967 song “Life in Prison,” Haggard subverts the triteness of what outlaw music had become at the time. He lived it and knew it wasn’t for everyone. Thus, he used his experience not to sell records to the masses, but instead to teach.

Jelly Roll

Jelly Roll has made his mark in turning his incarceration into a learning experience. Sentenced to a juvenile institution at 14, Jelly Roll dealt with legal troubles until his parole ended in 2016. Subsequently, he rose to the top of country music in 2022 after his successful singles “Son of a Sinner” and “Need a Favor.”

Jelly Roll often utilizes his experience to help those in similar positions. Since his success, he has started several programs to help people who have been incarcerated, and testified to Congress about the dangers of fentanyl. Needless to say, the man has turned himself into a beacon of hope for folks who share similar experiences.

David Crosby

The former guitarist for Crosby, Stills & Nash was arrested in Dallas in 1982 for possession of narcotics and a firearm. Subsequently, Crosby was sentenced to five years in prison and only served a few months before being released on parole. Before his arrest, Crosby’s cocaine addiction had spiraled, leading him to squander away much of his earnings.

Crosby claims prison saved his life. That being so, his remorseful transformation led him to write a letter of thanks to the judge who convicted him. Crosby used this experience to reinvent himself, and when he got out—well, he was a new man both to himself and his fans.

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