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.
Incredibly, a dude who’d never spent more than one night behind bars wrote one of the most authentic-sounding songs about prison in history. The Man in Black frequently performed free concerts for convicts — including at California’s Folsom Prison — and penned plenty other jailhouse tunes, including “Starkville City Jail” and “San Quentin.” But nearly 60 years later, “Folsom” still has the title of “best prison song” on lockdown.
Bob Dylan’s tragic true story about boxer Rubin “Hurricane” Carter. Included on 1976’s Desire, “Hurricane” profiled Carter’s wrongful conviction for a triple homicide in 1966. Despite little evidence tying Carter and his friend to the crime scene, a jury still convicted the boxer. Dylan’s song points out the police injustice in the case, and while the track helped gain support for a new trial, Carter was once again found guilty in 1976. Carter was finally released from prison almost 10 years later.
Perhaps the most upbeat song about prison in music history. This Leiber/Stoller hit was penned to accompany Presley’s Jailhouse Rock, a 1957 film about a young prisoner who discovers his musical skills behind bars. One of Rollling Stone‘s 500 Greatest Songs of All Time, the song has been covered by everyone from Jeff Beck to John Mellencamp to the Blues Brothers, who performed the song in Joliet Prison at the end of their 1980 film.
Released as a B-side to the 1977 single “Clash City Rockers,” this Joe Strummer-penned track gives a subtle nod to a trio of rockers who found themselves in trouble with the law: MC5’s Wayne Kramer, Fleetwood Mac’s Peter Green and the Rolling Stones’ Keith Richards. Kramer would later link up with Billy Bragg to create the Jail Guitar Doors initiative, which provides musical instruments to inmates.
Released in 2003, “Prison Grove” is Zevon’s stark depiction of an inmate in a jail constructed of iron and rock, with no heat, in the coldest winter. Adding weight to the track, it was recorded while Zevon was fending off terminal lung cancer, giving the song an air of a death sentence Zevon knows he can’t escape. Bruce Springsteen, T-Bone Burnett and others provide background vocals.
While the term “fish” in prison usually means a first-timer that’s in for a rude awakening, in the case of Waits’ track, the fish refers to actual fish. “Fish in the Jailhouse” briefly introduces us to Peoria Johnson, who tells his cellmate he can break out of any prison with a “skeleton fish key,” which he’ll get at supper because the jailhouse cafeteria is serving fish that night. The idea for the song reportedly came to Waits’ wife and co-writer Kathleen Brennan in a dream.
For their major label debut, Sublime covered this early Bob Marley & The Wailers single, combining Marley’s verses with their own take on Tenor Saw’s “Roll Call.” The result is one of the best tracks on Sublime, a tale about the never-ending struggle between the law and teenage angst.
Sometimes you don’t have to be in jail to be imprisoned. Soundgarden’s 1992 Badmotorfinger classic is a harrowing cut about captivity and the desperation to break free: “Cutting my teeth on bars and rusty chains. I’m gonna break my rusty cage and run.” No wonder it worked so well for prison-song master Johnny Cash, who covered it in 1996.
This 1983 track from Mike Muir’s long-running Los Angeles punk band tells the story of a different kind of confinement: A mental health facility. Much like prison changes a man, our protagonist fears the treatment at the institution — with its medications and lobotomies — will transform him from a dude with suicidal tendencies into a zombie of his former self. And all he wanted was a Pepsi.
Clocking in at just over 90 seconds, Greg Ginn’s 1981 tale of the police’s discrimination against the Los Angeles hardcore scene explodes like a flash grenade. “I go to court for my crime. Stand in line, pay bail. I may serve time,” grunts a frustrated Henry Rollins. This Damaged song also bridges the gap between the misdemeanors of “Spray Paint (The Walls)” and the imprisonment expressed in “Padded Cell.”
The biggest hit off Nas’ acclaimed debut Illmatic, “One Love” is a letter from the rapper to a buddy that’s in prison, updating him on what’s been going on in Queensbridge since his bid started. In one verse, Nas both congratulates his friend on the birth of his child and shares some bad news that his lady is messing around. It’s harrowing information, but Nas at least leaves half a hundred in the prisoner’s commissary to make it go down a little better.
The “November Rain” of gangsta rap, this hip-hop epic follows Snoop’s character from the streets of the LBC to the California Institute for Men in Chino. Along the way there are drive-bys, death and resurrection, deals with the Devil, weed smoke, Bible verses and ultimately, a ride on the “gray goose” to prison, where Snoop finds himself in the middle of an all-out shank war. This Dr. Dre-produced song was accompanied in 1994 by an equally epic 18-minute short film.
Sam Cooke’s upbeat 1960 hit “Chain Gang” was inspired by an actual encounter Cooke had with a prison chain gang while out on tour. Inmates were commissioned to build many of America’s public highways during this era as a means of cheap labor. As with many songs on the subject, the only thing keeping the prisoners in good spirits is the hope that one day they’ll be free from their shackles.
The song’s title says it all. The escapees are pursued by hound dogs and search lights until they make it into the city, where Thin Lizzy immediately start looking for some female company.
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.
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.
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.
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.
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.
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.