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Various Artists

Destination Jail (31 Prison Songs From Behind The Bars)

Review by Gary Hill
Another thematic compilation from Bear Family Records, this album’s focus is on songs about incarceration. The music here lands in a territory that ranges from country to old school rock and roll and some borders just on the pop side of that equation along with some definite folk elements. While not everything here is my thing, there are a lot of effective tracks on this set.

This review is available in book (paperback and hardcover) form in Music Street Journal: 2025  Volume 1. More information and purchase links can be found at: garyhillauthor.com/Music-Street-Journal-2025.
Track by Track Review
Billy Tidwell And The Chivells - Folsom Prison Blues

This song is a trademark number for Johnny Cash. This rendition is all class.

Webb Pierce – In The Jailhouse Now

There is a real downhome vibe to this track.

Rod Morris – Alabama Jailhouse

More of a rockabilly vibe is on the menu here.

Bill Carter – Shot Four Times And Dying

Country and rockabilly merge on this tune.

Ronnie Hawkins – The Ballad Of Caryl Chessman

This is more of a folk song. It’s classy.

Jim Carter - Jailer, Jailer

Energetic old school rock and roll is on the menu here. The vocals on this are low register and so cool.

The Pierce Brothers – Death Row

Another rockabilly tune, this is on the mellower end of that equation.

Gary Williams – Walla Walla State Prison

I love the surf styled guitar. This is a classy tune.

The Johnny Burnette Trio - Midnight Train

This acoustic guitar based tune has more of a country folk rock vibe.

Helen Grayco – Lilly's Lament (Cell 29)

The super-deep backing vocal just singing “29” is a cool touch. The female vocals are not only great, but also provide some variety. This whole song is just so classy. It has a great bluesy, jazzy kind of vibe to it. This is definitely one of my favorites here.

Jaycee Hill – Crash Out

This rockabilly jam has a real vocally dominated arrangement to it.

Sonny Burgess And The Pacers –Prisoner's Song (alt. 2)

I previously reviewed the “alt 1” version of this on another album. Here is what I said about it, “There is a real Dixieland jazz turned rock and roll vibe here. This is a fun romp that is among the best here.” The focus on rock and roll is pretty definite here, but that Dixieland presence still remains.

Troy Crane And The Three Texans – Huntsville Prison Blues

A classic country vibe is in place on this live recording. It’s nothing Earth-shattering, but it works well. The low vocals are a great touch, and I love the guitar fills on the track.

Skeets McDonald – Fort Worth Jail

The guitar picking on this is the best part for me. Beyond that, it’s a pretty basic country leaning tune. It does also have some cool piano work.

Curley Money – Chain Gang Charlie

An old-time rock and roller, this is classy stuff, but not really a standout.

Jimmie Skinner –One Dead Man Ago

More country based and stripped back, this has some great guitar fills.

Stonewall Jackson – Run

More of an acoustic country romp, this is solid stuff.

Bobby Sykes– The Guard On The North Wall

More of a vintage pop sound is on the agenda on this track. It has some hints of country, but is more mainstream than that. The backing vocals really add to that.

Bobby Darin – Jailer Bring Me Water

There is a gospel meets rock and roll groove to this track.

Reb Allen – Folsom Prison Blues

Here we get a different version of the track that opened the set. The other one was closer to the Johnny Cash rendition. This one feels more pop meets rock and roll in style.

Johnny Starr – Lewisburg Prison

This number feels a little like Johnny Cash. It’s alright, but not one of the standouts by any means.

Ron And Joe And The Crew – Riot In Cell Block No. 9

I dig the old-time rock and roll sound on this tune. The guitar has a classic sound, and the whole tune works so well.

Jimmy Young – Chain Gang

Rock and roll, jazz and more merge on this tune.

Johnny Rebb And His Rebels – Hey Sherriff

A playful 50s rock and roll thing is on the menu here. This is a fun one.

Bill Carter With The Cooper Brothers – Jailer Man

Country and folk seem to be merged on this piece. It has some Elvis like rock roll, too.

Jimmy Minor – Death Row

This slow dirge feels a lot like Johnny Cash.

Bill Monroe And His Bluegrass Boys – Prisoner's Song

There s a real down-home bluegrass vibe to this cut. It’s not really my kind of thing, but it does have some good energy and brings some variety.

Bill Flagg – Doin' My Time

This is more of a bluegrass meets country and folk sort of piece. It has good energy, but it’s not really a big winner for me.

Marty Robbins – The Hanging Tree

Bouncy, country leaning contemporary pop music is on the menu here. This is entertaining, but pretty vanilla.

George Champion – My Hanging Day

This groove has a lot of Johnny Cash type sound in the mix.

Bennie Hess – Walking That Last Mile
From the spoken introduction to the stripped back musical arrangement and vocals, this feels really downhome and amateurish. It also feels pained. I suppose folk music is the best description in terms of genre. If there is a song here I don’t like, this is it. That said, it certainly fits the theme.
 
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