Bob Dylan: the gambler

By Tony Attwood

I’ve not seen any articles about Bob Dylan and gambling as such, so I can’t say if Bob likes the odd flutter, but I can say that Bob does, from time to time sing about gambling.  And that of course is not surprising since it is one of the traditional themes of folk and contemporary music.

So I thought it might be interesting to compare the songs that he has written, arranged and performed, which take in this theme.   And as ever, if I have missed some songs from the list, do let me know.

One early and famous reference comes from “House of the Rising Sun” which of course is not a Dylan composition, but comes from a traditional source often known as “Rising Sun Blues”.  It’s the classic tale of the gambler who spends too much time at a night club with the ladies and the gambling tables.

If you know the version popularised by the Animals as performed by Bob sung on Freewheelin’ this version should come as an interesting surprise…

Now we move onto Rambling Gambling Willie which is a particularly confusing song as it turns up in several different versions by Bob.  I’m going to start with this one immediately because I think it is the stand out edition, but of course each to his/her own taste.

The original piece originated from the traditional song “Brennan on the Moor” and as the song has mutated over the years so the lyrics have wandered around all over the place.

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 the 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 (sorry about the video, but I can’t find another version of the recording on line).

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…

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

Willie is presented as a positive figure throughout…

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.

Now I am going to go on to a couple more Dylan songs which also include gambling themes, but it is of course possible that if you do fancy a little time playing blackjack, you’ll want some musical background – while keeping your Bob favourites for other occasions.  So being a helpful sort of chap, I’ve got a list of the best music other than Dylan to play while spending a little time on blackjack, which should help pass the time of day before you return to your Dylan tracks.

Which takes us on to Huck’s tune.

This was written for the movie Lucky You and is a song about poker, money and relationships.  If you haven’t played your copy of Tell Tale Signs for a while do go back and play it, and particularly this extraordinary piece.

And this takes us on to the final piece in my list, “Lily, Rosemary and the Jack of Hearts” about which I think we have published more articles than any other song.   Lily is the poker player of course and the theme of playing cards turns up all the way through the song.

And since all the songs in this little piece have been Dylan performances, here’s an alternative.  After all you’ll know the original so well, you don’t need me to offer it again.

One comment

  1. I suppose Frankie Lee (“The Ballad Of Frankie Lee And Judas Priest”) would deserve a prominent place in the line-up of Dylan’s Down-on-their-Luck Gamblers.
    As either decor or as a metaphor ‘to gamble’ or ‘card-playing’ does occur quite frequently (“Down the Highway”, “Bob Dylan’s Dream”, “It’s All Over Now, Baby Blue”, “Shelter From The Storm”, “Joey”, “Black Diamond Bay”, “Series Of Dreams”, “Standing On The Highway”, the list goes on), so I’d say you’re on to something.

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