Why does Bob Dylan like “Stone Walls and Steel Bars”

By Tony Attwood

Stone Walls and Steel Bars was written by Ray Pennington and Roy Marcum and was originally recorded by The Stanley Brothers in 1963.  Bob Dylan first played it on 23 August 1997 and played it a total of 37 times between then and 18 August 2002 when it got its final run out.

Here is a recording from a performance in California in 1998.


In terms of the song lyrics, I take it that the singer not only stole the other man’s wife but also murdered the husband, and is now about to go to the gas chamber.   That is, of course, reading quite a lot into this, although it is the only way I can explain that he is a “three times loser”: he murdered husband and wife (that’s two) and now is being killed by the state (three).

But I am known for totally misreading lyrics, so if there is a simple and clear explanation other than this, do let me know.  Although it could also be that the lyricist actually found two phrases he really liked: “Stone walls and steel bars” first and “three time loser” second, and simply melded them together.

Even if that second explanation is true and the song doesn’t really mean too much, it doesn’t stop it being a great piece of music.  Here are the lyrics in full…

Stone walls and steel bars, a love on my mind
I’m a three time loser, I’m long gone this time.

Jealousy has took my young life,
All for the love of another man’s wife.
I’ve had it coming, I’ve known all the time,
No more stone walls and steel bars and you on my mind.

Gray-haired warden, deep Frisco Bay,
Guards all around me leading my way.
I’ve had it coming, I’m at the end of the line,
No more stone walls and steel bars and you on my mind.

Stone walls and steel bars, a love on my mind,
I’m a three time loser, I’m long gone this time.

The first recording of the song that was released came in 1963 from the Stanley Brothers, and I’ve put a copy of that below these notes.

Ray Pennington, one of the co-composers of the song was a western swing performer, record producer and artists and repertoire manager with a record label – and indeed he produced of some Stanley Brothers records, as well as being an occasional drummer.

But although he clearly had a variety of talents, Pennington seemingly did not always have the success needed to keep the wolf from the door and there were times when (according to the histories I have found) he also worked in a record shop.

However in the 1960s he signed with Capitol Records and later Monument Records, recording a number of records himself, gaining some chart success, as well as finding that his compositions were now in demand.  Ultimately he had the much sought after number 1 hit with “I’m a rambling man” recorded by Waylon Jennings.

From 1984 onwards, Ray Pennington worked for his own record company Step One Records recording many successful songs and albums over the next four years.  After that he slowed down, and eventually took retirement – but as far as I know he is still with us, now aged 85.

As for his co-composer Roy Marcum, I regret I know very little except that apart from writing for the Stanley Brothers he also wrote for Ricky Scaggs.

Here is the first release on Stone Walls and Steel Bars from 1963.

And another version from Bob – rather different this time.

So to the question, why does Bob like this track?

First it has a great opportunity for those opening harmonies.  And the chord changes are unusual.   The chorus with which the song opens (and let us note that opening with the chorus is itself unusual) really sets the scene, and has an iconic feel because of those harmonies and the lyrics.

Then the verse opens not on the tonic – the basic chord of the song, but the dominant.  I can’t think of too many other songs that does this – Dylan does it in “Baby Blue” but not too many other times.   In fact, although only using the chords that we find in 95% of pop and rock songs, the whole of this song has a completely different feel from anything we might expect or anticipate.

And that I think is what makes the song so attractive to any musician looking for something different.  Plus then when combined with a couple of really good simple lyrical phrases, it is an absolute winner.

Finally, the lyrics, although short, have three really cracking lines within them.

Stone walls and steel bars
I’m a three time loser, I’m long gone this time.

I’ve had it coming, I’ve known all the time

These are all dead simple but really very effective and unusual lines.   Yes, there is a mawkishness in the whole piece, but we can maybe forget the meaning and listen to the overall effect!

Oh yes, and how many times do we hear Bob say “Oh you’re so kind” as the audience cheers?

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  1. “Stone walls do not a prion make
    Nor iron bars a cage”
    (Richard Lovelace: To Althea, From Prison)

    At least on this side of the pond, “Three time loser’ is an idiom for having a lot of bad luck…..perhaps related to three strikes in baseball??

  2. A third timer was given life in prison in some States …Alcatraz in Frisco Bay did not execute prisoners

  3. Two corrections — Ricky’s name is Skaggs with a “k.” Also, Ray Pennington passed away Oct. 7, 2020 at the age of 86. In addition to the song you profiled in this essay, he also wrote or co-wrote songs recorded by Waylon Jennings, Willie Nelson, Ray Price and other members of the Country Music Hall of Fame. Pennington was working at Ralph & Carter’s label, King Records, at the time the legendary brother duo covered the song.

    Ralph continued to perform “Stone Walls and Steel Bars” throughout his career. In 1997 he re-cut the song with Junior Brown in Nashville for “Clinch Mountain Country,” which also included Ralph’s duet with Dylan on “Lonesome River.”

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