Bob Dylan’s Rambling Gambling Willie: three versions including one masterpiece.

By Tony Attwood

This is the version of Rambling Gambling Willie that you might know from its revivals…

but stay with us, because there is another Rambling Gambling Willie which we’ll come to later.

The outsider, the outlaw, the loner, death.  Four concepts that dominated Bob Dylan’s thinking about songs, as he moved away from the first experimental compositions of 1961 into the total flowering of his talent in the following year.

And what appears to be the first two songs that Dylan wrote in 1962 take us through the two musical genres that attracted Dylan so much – the ballads from the Scottish and Irish tradition and the blues of Robert Johnson.

Dylan had already produced a blues so utterly perfect in Ballad for a friend , it was perhaps not surprising that he instantly turned to his other muse – the Scottish and Irish ballads, and the concept of the outsider.  Not the outsider as a down and out dying on the street as in Man on the street but a hero of the olden days, outside the law, but with the heart of gold.  In effect the myth of Robin Hood, as everyone brought up in England knows it.   (Incidentally Sherwood Forest is a real place, and less than an hour’s drive from where I live in the East Midlands.  The forest is still there and you can go and see the old oak tree under which Robin and his men supposedly gathered.)

Dylan’s composition comes from Brennan on the Moor – a song which I’ve known for much of my life, and which indeed I taught to my daughters as they were inducted into the array of song books and musical instruments that littered the house in their younger days.    There is a version of it by the Clancy Brothers online.   Brennan was an Irish Highwayman who was hanged in the early 19th century and whose exploits became romanticised.

The lyrics of this song vary enormously of course – here’s one version

Oh it’s of a brave young highway man this story I do tell
His name was Willie Brennan and from Ireland he did dwell
It was from the Kilworth Mountains he commenced his wild career
And many a wealthy nobleman before him shook with fear
Oh it’s Brennan on the Moor, Brennan on the Moor
Oh brave and undaunted was young Brennan on the Moor

Which we can compare with Dylan’s

Come around you rovin’ gamblers and a story I will tell
About the greatest gambler, you all should know him well
His name was Will O’Conley and he gambled all his life
He had twenty-seven children, yet he never had a wife
And it’s ride, Willie, ride, Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

The music is very similar indeed, and there is a strong connection in the lyrics too – not least by the fact that in both songs we have “Willie” although they were of course totally different characters.

Dylan’s character is based on Wild Bill Hickock (known as “Willie O’Conley” in the song) and it was intended to be part of his second album.  Interestingly, that album that we have always known as Freewheelin, was originally called Bob Dylan’s Blues, at least until late July 1962, when Dylan recorded “Rambling, Gambling Willie”.

The version in this video is really worth comparing with the version on Bootleg 1-3 and the Whitmark Version.  I guess it is an early version and came before either of the two recordings that are in the Bootleg series.  Perhaps someone can put me right on what this version is.

Returning to the version of the lyrics that is used in the two Bootleg series recordings, Dylan goes to some length to tell us what a great guy Willie was…

He gambled in the White House and in the railroad yards
Wherever there was people, there was Willie and his cards
He had the reputation as the gamblin’est man around
Wives would keep their husbands home when Willie came to town
And it’s ride, Willie, ride Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

It is in fact a romantic conception of the man – we are led to admire his gambling, not have any sympathy with the people from whom he took money…

Sailin’ down the Mississippi to a town called New Orleans
They’re still talkin’ about their card game on that Jackson River Queen
“I’ve come to win some money,” Gamblin’ Willie says
When the game finally ended up, the whole damn boat was his
And it’s ride, Willie, ride Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

Indeed even when Willie is taking money from regular working folk whose families would then presumably have no food for their children, we are asked to admire Willie…

Up in the Rocky Mountains in a town called Cripple Creek
There was an all-night poker game, lasted about a week
Nine hundred miners had laid their money down
When Willie finally left the room, he owned the whole damn town
And it’s ride, Willie, ride Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

And finally we do get to hear about why we should feel so good about him…

But Willie had a heart of gold and this I know is true
He supported all his children and all their mothers too
He wore no rings or fancy things, like other gamblers wore
He spread his money far and wide, to help the sick and the poor
And it’s ride, Willie, ride Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

Eventually Willie gets shot by a man who accuses him of cheating and he has the traditional dead man’s cards in his hands, the aces and eights.  And so the last verse tells us that when your time has come, that’s it, there is no escaping the cards, or death.

So all you rovin’ gamblers, wherever you might be
The moral of the story is very plain to see
Make your money while you can, before you have to stop
For when you pull that dead man’s hand, your gamblin’ days are up
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gamblin’ now, nobody really knows

That’s the song, but I would like to finish by focusing for a moment on the guitar work on the version that appears on Bootleg Series 1-3 (track 8) and the way Dylan’s singing works around it.

The guitar work is not exactly repeated verse by verse, and Dylan’s singing changes to, with very subtle rhythmic and accent changes.  Just listen to what Dylan does with “noBody knows” in the penultimate verse. In just listen to how Dylan sings those two words throughout the whole song.  That’s not the only way Dylan is varying the music as he goes, but it is an easy to hear example.

What’s more the chords that Dylan uses are not the obvious ones to accompany the melody, if you really want to hear just how Dylan makes this song develop, play it on the CD and then immediately flip back to the start and play it again – you’ll hear just how far Dylan has upped the intensity.

In short Dylan squeezes much, much more out of the music of this song than any lesser performer ever would both in terms of his guitar performance and his singing.

Had the Bootleg 1-3 version been released on Freewheelin it would have added another dimension to the appreciation of his work that accompanied the album as it was released.  It’s a fine adaptation of a classic song, but more than that it is an example of just how much Dylan could do with the guitar and lyrics this early in his career.

The Discussion Group

We now have a discussion group “Untold Dylan” on Facebook.  Just type the phrase in, on your Facebook page or go to  It is also a simple way of staying in touch with the latest reviews on this site.

The Chronology Files

There are reviews of Dylan’s compositions from all parts of his life, up to the most recent writings, but of late I have been trying to put these into chronological order, and fill in the gaps as I work.

All the songs reviewed on this site are also listed on the home page in alphabetical order – just scroll down a bit once you get there




  1. You ever hear Townes Van Zandt’s version? On You Tube it’s listed as Little Willie the Gambler.

  2. I’m not utterly convinced that’s Bob Dylan singing in this video. Sources?

  3. This is NOT Bob Dylan, it is not his voice, and he does not play guitar like that!!!

  4. Positively NOT Dylan singing or playing in the video. Sounds like it was recorded MUCH later than any extant Dylan version, too.

    I’d be curious to hear why you think even could possibly be Dylan…
    It’s not even a bad imitation. (Not that there is anything wrong with this attempt…it’s not bad…unless it was INTENDED to sound like Dylan!)

  5. Listening to the early recordings of Dylan what has always struck me is that way that he could change both his voice and his guitar technique. To my mind there is no Dylan vocal approach at this time, any more than there is a Dylan guitar technique. He is listening, imitating and experimenting throughout.

Leave a Reply

Your email address will not be published. Required fields are marked *