Condemned Playlist – 13 Haunting Songs About the Death Penalty


The executioner’s shadow has long loomed over music, with many artists penning chilling ballads meditating on the gallows. Spanning decades and genres, these songs provide poignant perspectives on capital punishment’s complex emotional and ethical dimensions.

Some tracks aim for gallows humor, like Johnny Cash’s “25 Minutes to Go,” which morbidly chronicles a man’s final moments before death by hanging. Others strike a somber, haunting tone, such as “The Long Black Veil,” in which a man chooses execution over exposing his affair with his best friend’s wife.

Several artists tackle real-life cases that illuminate flaws in the justice system. Elvis Costello’s “Let Him Dangle” examines the controversial execution of mentally disabled Derek Bentley in 1953 England. Meanwhile, Eddie Vedder’s “The Long Road” solemnly reflects on lives impacted by the death penalty.

Politically minded musicians like Steve Earle pull no punches, explicitly critiquing capital punishment in songs like “Ellis Unit One.” But oblique songwriters like Tom Waits prove condemnation can be implied, not overt, as in his abstract “The Fall of Troy.”

Other tracks highlight the condemned’s dismal longing for freedom, from Merle Haggard’s inmate lament “Sing Me Back Home” to Tom Jones’ fictionalized “The Green, Green Grass of Home.” Though the perspectives vary, each song aims for emotional potency over didactic moralizing.

The Thirteen

#1 Gallows Pole-Led Zeppelin (Traditional) – This is a centuries old song that appears to have been originally titled “The Maid Freed from the Gallows”. The song is about a condemned person who begs for the hangman to wait for his/her friends/family to arrive to bring the hangman a bribe to set them free.

#2 25 Minutes to Go-Johnny Cash (Shel Silverstein) – This song was first covered by Cash on his Sings the Ballads of the True West and later on his masterful At Folsom Prison. The song is gallows humor at its all time best. It literally details the last minutes of a man’s life before his execution by hanging.

#3 The Long Black Veil-The Band (Danny Dill and Marijohn Wilkin) – The Long Black Veil has got to be one of the most hauntingly sad songs ever written. Originally recorded by Lefty Frizzell in 1959, it has become a country music standard and has been covered by everyone from Mike Nesmith to Bruce Springsteen. The first time I heard the song, and fell in love with those sad lyrics, was the John Anderson version from his album Wild and Blue. The version I feature here is by the legendary The Band. Rick Danko’s voice as he sings of a man who would rather die than for his best friend to know a terrible secret sends a chill through my bones.

#4 Johnny 99-Bruce Springsteen (Bruce Springsteen) – I always wondered if Bruce Springsteen wasn’t inspired by the crimes of Gary Gilmore when he wrote this song. The main character, Ralph, murders a night clerk and is sentenced to die. Gilmore murdered a gas station attendant and a motel clerk and was sentenced to die. Both men request to be executed rather than rot away in prison. The song was covered by Johnny Cash and was the title of his 1983 album. The original version by Springsteen appeared on his stripped down masterpiece Nebraska.

#5 The Mercy Seat-Nick Cave and the Bad Seeds (Nick Cave and Mick Harvey) – It’s a bit embarrassing to admit that, up to a few weeks ago, I had never heard of this song. But as I was doing a search for songs about capital punishment this was one of the first songs mentioned. The Mercy Seat within the song is of two places; the electric chair where this man will be put to death, and the Throne of God where he will stand before Him. There are several Biblical references within the song. I don’t really know what more to say about it except that I wish I had heard it a long time ago.

#6 I’m Not the Man – 10,000 Maniacs (Natalie Merchant) – This song has some good lyrics. The only thing is that the music and the singing make me think of Bananarama on Quaaludes. The song is one of those “I was framed, somebody is going free while I swing from the rope” songs. Merchant throws in a reference to the KKK, giving it an edge of racism. If I heard this song on American Bandstand I would say “Well, Dick, it’s got some catchy words, but I’d rather take a nap than dance to it.” By the way, would a song about a man being hanged fall under the classification of ‘swing music’?

#7 Let Him Dangle-Elvis Costello (Declan McManus) – Let me get this straight; Derek Bentley was a simple-minded (mentally retarded?) 18 year old boy who didn’t pull the trigger. Am I right so far? Christopher Craig was a 16 year old hoodlum who did pull the trigger because Bentley said “Let him have it, Chris!” Craig was too young to hang, so basically in a case of one hand washing the other Bentley took his place. I learned of this case from the film Let Him Have It, directed by Peter Medak. When I heard the song and read the lyrics on Elvis Costello’s Spike, I shouted out “Let him have it! I know what this is about!” Derek Bentley was hanged in 1953 for the crime, but was fully pardoned in 1998. Too little, too late.

#8 The Fall of Troy – Tom Waits (Tom Waits and Kathleen Brennan) – Tom Waits is the only artist I know who can write and sing a death penalty song without actually mentioning anything to do with capital punishment itself. From what I can surmise, the song is more about the effect of the crime and the punishment on the families of the criminals and the victims. If anyone gets any different meaning out of this I would love to hear it.

#9 Ellis Unit One-Steve Earle (Steve Earle) – I originally heard this song on the Dead Man Walking soundtrack. Earle is a very outspoken opponent of the death penalty and this song, along with his Over Yonder (Jonathan’s Song)is one of his strongest statements. I’ve been a fan of Earle’s for quite a long time and this is one of my favorite songs of his. I may not share his philosophies, but like the saying goes I will defend his right to those philosophies.

#10 Over Yonder (Jonathan’s Song) – Steve Earle (Steve Earle) – A companion piece to Earle’s Ellis Unit One. Enough said.

#11 The Long Road-Eddie Vedder with Nusrat Fateh Ali Khan (Eddie Vedder) – Okay, so I take back what I said earlier about Tom Waits. Apparently Eddie Vedder can write a song about the death penalty without actually mentioning it, too. This is also from the Dead Man Walking soundtrack. I’m not a big Pearl Jam fan, but I do feel that this is some of Vedder’s best singing.

#12 Sing Me Back Home-Merle Haggard (Merle Haggard) – A condemned man longs for the good old days once again. This is probably Haggard’s most well known song. All I know is that there was no damn way I could write a post about death penalty songs and not include this one. Karaoke nearly ruined the song for me as every redneck in a five mile radius had to put his or her spin on it. It’s like a friend of mine said when Run-DMC covered Walk This Way: You don’t f**k with a classic.

#13 The Green, Green Grass of Home-Tom Jones (Claude ‘Curly’ Putnam, Jr,) – Have you ever read An Occurrence at Owl Creek Bridge by Ambrose Bierce? It’s about a Confederate sympathizer sentenced to hang. Suddenly, he is free and running for home. As he runs to the loving arms of his wife he feels a jerk and a snap of his neck. He was never free. It was his life as he longed for it to be flashing before his eyes. This song could easily be the lyrical companion to the story.’ improve and expand as a longform article

This haunting playlist provides a thought-provoking tour through music’s relationship with the gallows, inviting listeners to confront the ethical dilemmas woven into state-sanctioned death. Some tracks celebrate the last pleasure of the condemned, while othersquestion a flawed system. But they all remind us that songs about life and death remain music’s most stirring, indelible form. The hangman may cast his shadow, but the humanity in these artists’ words persists.