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Between the Bars: 20 Great Songs About Prison

From Snoop’s murder case to Thin Lizzy’s escape and Johnny Cash’s blues

elvis presley jail

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The trials and tribulations of prison life have long been a fascination to musicians outside of the penitentiary walls. Whether it’s Johnny Cash shooting a man in Reno or Public Enemy looking for the fence, the fear of incarceration has haunted countless artists — but it also inspired them to write some killer songs. Fortunately for the rest of us, we can experience being behind bars vicariously thanks to television shows like Orange Is the New Black and Oz, films like The Shawshank Redemption, and the songs included here. From “Jailhouse Rock” and “Jailbreak” here are 20 of the biggest songs about the big house.

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James Brown & The Famous Flames, “Prisoner of Love”

Penned in 1931, “Prisoner of Love” was a hit for Ross Columbo, Perry Como and the Inkspots… but the essential version belongs to James Brown, who recorded his take in 1963. There are no bars and no wardens, as the title suggests, Brown is serving a different kind of life sentence: Marriage.

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Public Enemy, “Black Steel in the Hour of Chaos”

A detailed odyssey about a draft dodger and a massive jailbreak. After a correctional officer falls asleep on the job, our protagonist secures the C.O.’s “black steel” and the plan goes into action, leaving a trail of bodies and the titular chaos in its wake. 

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Nate Dogg feat. Snoop Dogg, “Never Leave Me Alone”

Framed within Nate Dogg’s 1998 G-Funk ballad about an O.G. torn between a life of love and a life of crime, Snoop delivers an insightful verse from the prisoner’s perspective. “Somebody was naughty when they snitched on me and the judge just sentenced me to do about a century,” Snoop says, later fretting about whether his baby boo is being faithful on the outside.

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Skip Spence, “Weighted Down”

Skip Spence, once a member of both Jefferson Airplane and Moby Grape, had a promising career in music cut short following a diagnosis for schizophrenia. In 1968, at the height of his success, Spence had a breakdown in New York and was confined to mental wards like Bellevue and the Tombs, where he wrote songs that appeared on his lone solo LP, the psychedelic classic Oar. “Weighted Down (The Prison Song)” written during his stay in those institutions.

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Merle Haggard, “Life in Prison”

The forefather of outlaw country, Merle Haggard’s 1967 album I’m a Lonesome Fugitive was stocked with songs about crime and punishment, including this track about a man sentenced to life behind bars for killing his wife in a fit of rage. “Life in Prison” was famously covered by the Byrds for their album Sweetheart of the Rodeo.

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Louvin Brothers, “Knoxville Girl”

One of the creepiest songs ever, this is what a traditional Appalachian murder ballad sounds like being retold by an angelic brother duo. It starts innocently enough, with some guy by chance meeting a nice girl in Knoxville. By the second verse, things get dark: He beats her to death, throws her body in the river, comes home with bloodied clothes, has a nightmare, wakes up surrounded by the townspeople and is left to rot for life in a prison cell — all in the span of four minutes. While this song would even be taboo by today’s standards, keep in mind that the Louvins’ version of the track came out in 1956. 

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