A look back at Dylan’s songs about gambling: and one of Bob’s favourites

By Jack Beam

It’s quite a while since we did a review of Bob Dylan’s compositions over time on the subject of gambling, but I am always willing to oblige when the subject comes up, (as indeed it did in the Untold Dylan office this week), because I’m instantly drawn, not to a Bob Dylan song, but to one of the songs he put in his own personal top ten of songs written by other people.  But more on that in a moment.

The subject came up from UK BTC casino and I was rather pleased about that as it led me onto the question: what was that song about gambling that Dylan liked so much?

Just in case you don’t know what song that eventually led me on to is I’ll keep you waiting til the end of this little piece, with a promise that all will be reevealed, along with a reminder to pay more attention in future!   But in the interim, it’s not a bad idea to go over one of two of Bob’s songs in the genre, and pick out one or two recordings that perhaps you might have missed.

The earliest data we have on Bob writing a song about gambling is “Rambling, Gambling Willie” which appeared on the Whitmark demo of 1962.

Interestingly (to me if no one else) for this live recording, they’ve changed key from the recording.  And I do love the way an extra bar is added in places.   In fact I love all of it.   Especially the notion of going through all this and claiming to be an innocent by-stander.  Fabulous.

I first knew of Warren Zevon, because of “Werewolves of London”, but nothing more, so it was learning of Dylan’s admiration, took me further into his music.  He was, it seems, born in the same year as me but died of cancer 20 years ago.   (And that is quite an unsettling thought: how come I, just a regular guy who enjoys all this music, managed to survive?  Beats me.)

I’ve featured the song before, but here’s a live version recorded for TV that I don’t think I’ve put up previously.  Of course, certainly in the UK at least, today you don’t have to go to Havana to have a flutter which makes life easier.   And I do so love this song.

As ever, I hope you found something in this piece that you enjoyed.

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