Gypsy Lou: Dylan’s transition. The meaning of the music and the lyrics.

By Tony Attwood

Dylan’s interest in and involvement with the Beat Generation is well documented, and his experimentation with different forms of writing comes in many parts from those early influences.  Dylan’s use of the blues, folk, pop, and rock formats to take us to all sorts of new destinations combining new style, illicit drugs, the examination and re-examination of all types of religion, attacks on materialism, and an eternal concern with people… it is all the Beat Generation.

And in among this all is that desire for bohemianism and spontaneity as ways of discovering new art forms.  Ginsberg did it was Howl, Burroughs with the Naked Lunch, Kerouac with On the Road, and Dylan with…

Ah that’s the problem.  Dylan, in the early stages, was not a Beat Poet, nor a Beat Musician.  He was nowhere near as radical as Ginsberg, Burroughs and Kerouac.  He was in fact re-working the models of folk music and the blues.  We find the occasional little experiment, like Motorpsycho Nightmare but the real leap comes with Subterranean Homesick Blues – Dylan’s first real Beat Poet piece.

So what we have is Dylan interested in, perhaps fascinated by the Beat movement, friends with the leaders, but not artistically not really able to find his way in.  .

Dylan made little mention of the dilemma at the start – at least until Gypsy Lou – which is, in the fashion of his reportage songs, the abbreviated story of Jon and Gypsy Lou Webb who together in New Orleans were at the heart of the local Beat community.


It was written around 1961/2 (so just before “Bob Dylan” was recorded) and recorded in August 1963 (around the time of Freewheelin).  My point is that it emerged before Dylan had any idea how to balance his interest in the Beat Generation and its poetry, with his own music, which was dominated by old English and American folk songs, and the blues of the 1920s.

Gypsy Lou, the subject of Dylan’s 1961/2 song was the magazine’s typesetter, (and creator and retailer of hand-tinted French Quarter cityscapes and small paintings to tourists on Royal Street).

The French Quarter of New Orleans was very much an artist, beat, creative, free spirit environment where social outcasts existed side by side with the genuinely talent artists – exactly the sort of place Dylan found exciting and intriguing in his early writing career.  Gypsy Lou sold her original works of art on the street, as Jon worked as a freelance writer and editor while together they ran the Loujon Press and its magazine (The Outsider) for what they called “Bohemian fugitives”.  Exactly something we can imagine Dylan being attracted to – after all he was already writing and singing songs about exactly such people – and continued to do so for many years.

Gregory Corso and William Burroughs contributed to the magazine which did two things (apart from having incredibly influential content).  It ran 3000 copies of each edition (unheard of at the time) and the publishers sent free copies to university libraries – which spread the word, even if it didn’t get too many subscriptions.

Jon and Gypsy Lou’s also moved into book publishing and had a hit with Charles Bukowski’s poetry: “It Catches My Heart in Its Hands” which made their name.  They also published two books by Henry Miller, all typeset by Gypsy Lou and printed by Jon, in their own home.

It was at this time that Gypsy Lou gained her reputation.  “Fiery” “flamboyant” and “jagged” were words used, but it was Jon (not Gypsy Lou as Dylan suggests in the song) who bungled the robbery of a jewellery shop and served three years in prison – an experience which he turned into a novel.  That’s the sort of life they lived.  At one stage they sold all their furniture and were living on the edge of survival.  Somehow it seemed to fit the model.

So here we have the bohemians, the eccentrics, the outsiders, the sort of people that Dylan came to write about later.  If you want a source for

The ghost of Belle Starr she hands down her wits
To Jezebel the nun she violently knits
A bald wig for Jack the Ripper who sits
At the head of the chamber of commerce

Mama’s in the fact’ry
She ain’t got no shoes
Daddy’s in the alley
He’s lookin’ for the fuse
I’m in the kitchen
With the tombstone blues

then quite simply it was this setting.  It was Gypsy Lou and her husband and the gang, only it took Dylan a few years to find a way to express it.  At first, it seems (at least from this song) it was all too much to take.

Jon and Gypsy Lou left the town in 1965 (by which time Subterranean Homesick Blues, Tombstone Blues and of course Desolation Row were written and recorded).   Dylan was moving on musically, Jon and Gypsy Lou were moving to Santa Fe, New Mexico, probably to escape debts.  Examples of their work is now housed in museums that celebrate the Beat era.  Jon died in 1971, but Gypsy Lou lived on – at least until her late 90s.

Gypsy Lou probably never heard Dylan’s song about her, and if she had, I guess she would just have shrugged.  But what we have to remember is that it is a sketch written out of frustration – frustration that Dylan has not yet found a way out of his dominant influences to become what he wanted to become (and of course ultimately did become) the first man to take the Beat Generation into its own unique form of music.

Tragically the only review of the song I have sound is derisory in the extreme, dismissing it as a work of no importance, saying it “does little to retain its grip on the listener’s attention.  One doubts the song detained its author long.”

Maybe that final point is right – it was after all a sketch – but enough of a sketch for Dylan to record it.  Gypsy Lou was clearly on his mind and thank goodness the Whitmark recordings exist because they do give us this insight into what Dylan was going through trying to sort out how he felt about the Beat Generation.

Of course in one way Gypsy Lou from volume 2 of the Whitmark albums is a simplistic three chord piece with a three line chorus that tells us nothing.  But listen more closely and Dylan is playing little tricks.  The way the melody subtly changes between the first and second verse, the long unexpected held “hey” and the use of “round the bend”.  Does that mean “crazy” or does it mean (as it would to the Beat Poets) exploring the unexplored, visiting new territory….

If you getcha one girl, better get two
Case you run into Gypsy Lou
She’s a ramblin’ woman with a ramblin’ mind
Always leavin’ somebody behind
Hey, ’round the bend
Gypsy Lou’s gone again
Gypsy Lou’s gone again

Thus Gypsy Lou represents the whole Beat movement in the song – he follows the movement around, until it drives him crazy, rather that specifically following the woman herself.

Well, I seen the whole country through
Just to find Gypsy Lou
Seen it up, seen it down
Followin’ Gypsy Lou around
Hey, ’round the bend
Gypsy Lou’s gone again
Gypsy Lou’s gone again

And isn’t that like the Beat Movement – always on the move.  Which is how Dylan caught up with it when he wrote Subterranean Homesick Blues – that blues that isn’t a blues, symbolising the world that many of the beat poets lived in.  Indeed Kerouac’s novel The Subterraneans about the Beat Generation, is clearly a reference point.

Certainly the world of the Beat Poets was one of late night drinking, fighting, sexual liberation, and from time to time writing stuff, much of which is best ignored, but some of which is occasionally brilliant.

But Dylan is not tied down with facts in his Gypsy Lou song.  There is no suggestion in the records that Jon committed suicide (he died in Nashville in 1971). But Bukowski later wrote a poem about the morning after Jon’s death “the dead are dead, there’s nothing we can do about it. Let’s go to bed…”   Gypsy Lou was reportedly not amused.

After Jon died Gypsy Lou moved back to New Orleans and developed her role as respected eccentric and bohemian

So she was not the character Dylan painted, and this was not the life Dylan painted – although the stories about her abounded, such as the one that said she wore he dead husband’s ashes in a container around her neck.  The story that she ingested some of these over the years is also certainly untrue – but was the sort of story she encouraged.

She continued to work through later life, including being the narrator in the movie, The Outsiders of New Orelans in 2007.

Gypsy Lou Webb with Noel Rockmore, right, and a friend.

This in a real sense Gypsy Lou is a trial run for Tombstone Blues and similar unfathomable stories.  We can see who Gypsy Lou is but we shouldn’t take it seriously.

Well, seen her up in old Cheyenne
Turned my head and away she ran
From Denver Town to Wichita
Last I heard she’s in Arkansas
Hey, ’round the bend
Gypsy Lou’s gone again
Gypsy Lou’s gone again

This is not literal travel – not at all.  Dylan is seeing Gypsy Lou as an artist always exploring new territory – an avant garde artist so dedicated to change that you’ll be hard pushed to catch up.

Well, I tell you what if you want to do
Tell you what, you’ll wear out your shoes
If you want to wear out your shoes
Try and follow Gypsy Lou
Hey, gone again
Gypsy Lou’s ’round the bend
Gypsy Lou’s ’round the bend

The reference to the calaboose (a jail, I should explain, and I had to look it up myself.  It’s not a word we have in English English), and the suicide is as I have said, unrelated to anything in the real Gypsy Lou story.

Well, the last I heard of Gypsy Lou
She’s in a Memphis calaboose
She left one too many a boy behind
He committed suicide
Hey, you can’t win
Gypsy Lou’s gone again
Gypsy Lou’s gone again

So let me come back to my main point.  This is a sketch – playing with an idea.  Dylan is influenced by the Beat Generation, but doesn’t know how to translate this into music and lyrics.  Listen to the rest of the album  and you’ll see that he’s not yet making the break forward.  He’s only a year or two away, and this is a vital document on the road to that break through.  It is fun, but fun that arises out of frustration.

Untold Dylan – an index to all the songs


  1. Is that old Bill Burroughs in that last photo with Gypsy Lou and Noel Rockmore?

  2. It is Robert Paige. In the early 70s, Rockmore took a street person under his wing that happened to be a former business person who was done on his luck and up in age. His name was Robert Paige but Rockmore just called him O.M. (for Old Man) and helped provide a place for him to live and work for him to do. Gypsy Lou Webb was living with Rockmore right after her husband Jon died in the Skyscraper (4 Story building at Royal & St. Peter). Robert and Gypsy Lou often posed for Rockmore who found them interesting characters to be with and to paint. Besides doing prep work on canvases for Rockmore, Rockmore also encouraged Robert to paint works on his own just like he did for Gypsy Lou Webb. We have only seen one Robert Paige (Signed R.P.) but it was quite good. We try and see Gypsy Lou once a month, she is 98 in a great nursing home. About a year ago she told us the story of Bob Dylan and this song. Thanks for doing the article Tony. Well done!

  3. Rich, thank you so, so, much for writing in. My interpretation of the song was of course me just following the logic and the bits and pieces I could put together – I have never seen anyone else go down this route. To think that Gypsy Lou confirmed it is actually overwhelming.

    I really do appreciate your reading the article, and your comments above.

    I’m knocked out.


  4. Enjoyed your article. Lou herself wanted to write music. I don’t know of anything she wrote except LONG DISTANCE BLUES for Punch Miller that went public. She told me that she had a notebook full of lyrics. I have yet to see it. I’m a romantic and I like
    to think that Jon realized his health and lack of funds was going to make it difficult to
    continue publishing. They went to Nashville I believe because after years of chasing his dreams he wanted to give Lou a chance to try and follow hers. There she wanted
    to call on those in the music industry to see if they would be interested in her work.
    Alas Jon died soon after they arrived there.
    Just an aside but indeed it is true that Lou had a small vile of Jon’s ashes
    on a chain around her neck and when I saw her when she first returned to New Orleans and was working in a T-shirt shop in the Quarter she would open the vile and put an ash or two on her tongue. She so loved Jon. To her it was a natural act.
    Ed Blair

  5. It’s interesting to me that Dylan personally refused permission for the use of his song “Gypsy Lou” in my film about her and Jon Webb which you refer to in the piece above. It made me wonder if, in fact, the song is really about her at all, even though she is a wonderful lady still alive at 100 in a nursing home in Slidell, LA. The film can be found at
    Wayne Ewing – Producer/Director “The Outsiders of New Orleans: Loujon Press”

  6. Hi! My dad just fwd’d all us Webbs your wonderful article on Jon & Lou! I only found out I had such amazing relatives in 2007! Jon was my great uncle from my dad’s side and we had never heard ANYTHING about him until my Uncle discovered the documentary about them. After learning about Jon & Lou’s amazing life I decided on a road trip in 2009 to make a stop in New Orleans to find Lou! She was living in Slidell with her sister and I spent the whole day with her – she was in her 90’s -but still a fiery soul, what a hoot! She actually told me about the song & when she that she had never heard it – I just pulled it up on YouTube on my phone and played it for her!!! She said it wasn’t about her, just named after her, and yes – she just laughed and shrugged it off. Just thought it would be fun to share with you that story. Again, it was so great to read your article about Lou and Dylan’s song!

  7. Kirsty – thank you so much for your kind comment. And I can’t tell you how much it means to me to know that not only has my little article been read, but is actually being passed around and used as a reference point.

    I just have an interest in going through the songs and trying to trace them back to their point of origin – and I do have a bit of knowledge of the issues that the song refers to, which helps to make a bit more sense of it all. But I never thought I would be reaching out to people such as yourself. It is Christmas Eve as I write this, and you have really warmed up my Christmas! Thank you.

  8. It’s great to see Lou Webb getting the attention she deserves. If you want to learn more about her and Jon, I invite you to read my book, Bohemian New Orleans: The Story of the Outsider and Loujon Press. Lou told me that she met Dylan in the French Quarter, and she swore his song was about her. I didn’t address it in my book, because I couldn’t verify that she was correct, and really, how could she know for sure? But I fall on the side of believing it’s true. “Gypsy Lou” is a pretty distinctive and rare name, after all, and Lou was a well-known figure in the Quarter in those days.

    I enjoyed your article, but I have a caveat: Unless I’m missing your meaning about Jon’s death, he didn’t commit suicide. Rather, he died in Nashville of complications after surgery to remove an arterial blockage.

    Thanks for putting the spotlight again on the wonderful Webbs.

  9. I have two of her paintings on my wall framed in really nice frames and then I started doing research and I really like the story of John and her so then I bought another drawing and the lady I asked her to send me the matting because it’s signed by her and there is a mark a stamp.. and the question I was researching right now is the value of those and I can’t find it.. I have the second Outsider I have the DVD and they all Belong Together and I know if I sell them separately I could get more but I have to move and I want somebody that will cherish them to have them it’s not really about the money.. but I’m pretty poor and I could use the money to move don’t ask your landlord to fix something if you’re on Section 8.. Richard Seibert will throw you out on your ass oh wait terminate your lease say he’s selling the house whatever but that’s where I’m at I’ve been trying to write a song is there any music when Dylan’s gone.. Dylan’s gone is there any music when we’re all gone.. they got Ai and Auto-Tune they can take that crap and to the Moon LOL I wonder if he uses it I think it’s like raping your art and even if you suck you don’t want to do that.. although I have heard songs but it sounds good from c h e r and others that was her Comeback song I forgot what it was I’m 62 I can remember s*** from the ’60s but I can’t remember what the hell I want to get in the kitchen.. I honestly wanted to give them to Dylan but I won’t get to even though he’s coming here I’m not rich to meet people well I don’t know if they have a meet and greet but it’s probably $2,000.. at Darien Six Flags people can afford to go can’t afford to eat or drink beer.. it was really hot out we were watching Crosby Stills and Nash they opened for Tom Petty and I had one of those big beers I don’t know 20 oz was $13 that was years ago.. I like people not to be behind me so I’m up by the fence and I dumped my beer oh man and I picked it up and it fell just the right way so I didn’t spill any thank you LOL you answered my question the question is the song by Dylan about Gypsy Lou Webb I think you may have answered it but only Dylan would really know.. and I don’t have a way to contact him.. I am a local artist in Batavia New York I do photography and I get frowned upon because other artists think it’s not art but if you do it the right way it is.. I think I sold about 10 images in my life. You don’t do art to get paid you can ask the local musicians.. man I really want to see Dylan but I’m moving to Rochester so I doubt it.. thanks for the information I really don’t want to pay money to find out the value but I got two of them for $3 at the Salvation Army where I don’t go anymore cuz I I’m a reformed hoarder and after I watched the show I quit but I never collected garbage like they do but it did affect my children there was stuff of mine in their room.. yeah this is a really good story.. if you go through the internet you can find images of her anybody want to buy a gypsy l o u web collection?? I can’t sell it on eBay because I’m disabled we’re not allowed to have money if you make more than $80 they take half of it isn’t that nice?? We still have to fight for our rights being physically challenged you surely notice when you can’t get in the bathroom and you have to hop in there on one leg cuz you’re in one of those carts and some people use them when they don’t need to so some people that need them can’t.. man I wish I could meet Dylan Someday I bet he’s so cool like really mellow totally the opposite of me.. you know it’s a good song when it paints an image on your mind.. that is why he should paint pictures of a song he’d be rich oh wait he already is.. I hope he didn’t sell his music but I guess he can’t take it with you.. I don’t know if I would if I was in that situation which I’ll never be.. it seems like castrating yourself.. no it won’t let me copy it and now I lost it oh well

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