"Top Five" songs about jail and prison

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Living vicariously through the words of another is one of the greatest and most powerful things a song can do for someone, especially in this case. No one wants to go to prison, but there has always been a love affair with outlaws in our culture. Pop culture has been intrigued by the struggle between good guys and bad guys since they were signified in western films by white and black cowboy hats. Here are five songs that deal with the various experiences of being locked up. Listen to them instead of going on that crime spree you’ve been planning.

“54-46 (That’s My Number)” – Toots and the Maytals
This autobiographical 1968 classic was one of the first ska songs to gain any kind of popularity outside of Jamaica and has continued to stay fresh over the years with periodic cover versions – most notably by Sublime in 1992 – keeping it alive for new generations to enjoy. Fred “Toots” Hibbert wrote this song following his release from prison for marijuana possession. 54-46 refers to his prisoner identification number while incarcerated, and the song is dually a lamentation on his arrest and subsequent prison stay, but it’s also a statement on the revolving door of the system when Hibbert sings “54-46 was my number/ Right now, someone else has that number.”

“Jailbreak” – AC/DC
AC/DC is best known for simple, raunchy, three-chord, blues-based songs about women and partying, but occasionally they delve into more serious subjects. This is especially true in the era before original frontman Bon Scott died of acute alcohol poisoning in 1980. This song, originally released in 1976, chronicles the sentencing, jailing and subsequent escape of a murderer. It’s complete with the adept guitar work of Angus Young and a worthy backbeat courtesy of ever-revolving members of the band’s powerful rhythm section. The lyrics “There was a friend of mine on murder/ And the judge’s gavel fell/ Jury found him guilty/ Gave him sixteen years in hell/ He said I ain’t spending my life here/ I ain’t living alone/ Ain’t breaking no rocks on the chain gang/ I’m breakin’ out and headin’ home/ Gonna make a jailbreak/ And I’m lookin’ towards the sky/ I’m gonna make a jailbreak/ Oh, how I wish that I could fly,” paint a straightforward picture of a scene that ends with an escape attempt that yields a “bullet in his back.”

“Folsom Prison Blues” – Johnny Cash
Being that this is a list that each week tries to avoid clichéd, overplayed and tired songs, this one almost didn’t make the cut. It is close to impossible to go to a bar where there’s a man over 50-years-old or a bunch of lame, Mike Ness-worshipping, rockabilly greasers pumping dollars into a jukebox just to get the chance to sing along to this song and act like it has some profound meaning to them. However, it is also ridiculous to leave a great song off such an aptly appropriate list just because of the people who listen to it. Plus, how can you exclude a song that features the line “I shot a man in Reno, just to watch him die” from a best prison songs list?

“Care of Cell 44” – The Zombies
This song is notable for a few reasons. First and foremost, it appears on an awesome slice of 60s psychedelic pop: the album “Odessey and Oracle.” Second, it is written from the perspective of a man in prison reading a letter from his sweetie, which might be unprecedented. And finally, it’s one of the most sonically upbeat (almost Beach Boys-esque complete with four-part harmonies) and lyrically optimistic songs about prison ever penned. If the lyrics “Good morning to you I hope you’re feeling better baby/ Thinking of me while you are far away/ Counting the days until they set you free again/ Writing this letter hoping you’re OK/ Saved you the room you used to stay in every Sunday/ The one that is warmed by sunshine every day/ And we’ll get to know each other for a second time/ And then you can tell me ‘bout your prison stay/ Feels so good/ You’re coming home soon!” are any indication, this guy’s troubles will soon be over.

“Holloway Jail” – The Kinks
The Davies brothers have always had a knack for concise storytelling set to snappy and jangly pop tracks, but this is truly one of their greatest. This song succeeds on many levels, but most notably, it is interesting because it’s about a female prisoner whose prison sentence is being lamented by her male companion. It’s hard to imagine there are many other songs out there about imprisoned females – in fact, until recently it was rarely discussed at all aside from in low-budget softcore porn on Cinemax. But the Kinks – always pioneers – explored the subject matter on this 1971 release that features the sweetly depressing lyrics “They took my baby, down Holloway jail/ They took my baby to Holloway jail/ There ain’t no pity, there ain’t no bail/ And she assures me that it’s living hell/ She was young and ever so pretty/ Now she looks so old and pale/ She never sees the day/ She wastes her life away/ Sitting in that prison cell.”
Compiled by Jason Yurgartis.