Leopard skin pill-box hat

By Tony Attwood

Some 45 years on, working through the first LP of the original Blonde on Blonde album is a bemusing and confusing affair.  There’s the knock about Rainy Day Women as an opening track – a scene setter, a statement about Dylan’s adoption of electric rock as a way of expressing himself.  Then the confused love blues of Pledging my Time, before the atmospheric brilliance of visions of Johanna, and the disdain of One of Us Must Know.

We turn the LP over and get the bubblegum effect of I want you, the absolute confusion of Memphis Blues Again, and then, the strange world of Leopard Skin pill box hat.

Leopard Skin is amusing, first time around, and somewhat surreal with the doctor and the new boyfriend wearing the woman’s hat.  OK, but so what?

This seems to be a song of disdain, certainly of sarcasm – making the hat the most important object in the woman’s life.  Well, yes, there are both men and women like that, but surely it doesn’t need a Dylan song to point it out.

So what are we to make of this song, and indeed of an album, whose first LP contains such a strange mixture?  With anyone else we might say that some of the songs are nothing more than throw aways, there to make up the number because the singer hadn’t written enough worthwhile pieces to fill up the album.  But surely not with Dylan, for as the subsequent release of some of the many unused recordings of the era shows, Dylan has always had more than enough music to put together in an LP.  And besides, if this was a real problem of writer’s block, why not put out a single album, as Dylan did for the rest of the LP era.

Looking at the opening lines of Pill-box hat there really is nothing here to show us why this song is here…

Well, I see you got your brand new leopard-skin pill-box hat
Yes, I see you got your brand new leopard-skin pill-box hat
Well, you must tell me, baby
How your head feels under somethin’ like that
Under your brand new leopard-skin pill-box hat

And that’s the problem.  It is not a distinguished song, it is not insightful, it is not atmospheric.  It is a jangly bumpy blues, and unlike all the other songs of distain it is just rather ordinary.

What it does show is that the old blues format can be used for anything, from the original “I woke up this morning” to a song about a woman’s hat.   Well, yes, but do we really need to know?

Some of the imagery is quite amusing as with

You know it balances on your head
Just like a mattress balances
On a bottle of wine

But really, from the man who gave us Desolation Row, and Rolling Stone, what is the point of it all?

In the last review I wrote, I considered Stuck inside of Mobile with the Memphis Blues again, and was able to find a connection between the town of Mobile with the writer of the Memphis Blues.  Here I can find nothing, no redeeming feature nothing.  Maybe it is there, but if so, at the moment it is beyond me.



  1. “Leopardskin Pill-Box Hat” was written in the era when birth-control pills first became readily available. That’s why the doctor is there, and the boyfriend as well. No one was wearing pill-box hats in the early sixties, so that alone suggests the song isn’t about the hat.
    As for the leopardskin aspect, I’ve always connected it with Leporello (whose name means little leopard) in Mozart’s opera Don Giovanni, specifically the scene where Leporello unrolls a long scroll on which are listed the thousand and one names of Don Giovanni’s conquests – all the spots he’s hit.
    So the question of “how does your head feel” while knowing you’re under the protection of a particular pill and for the first time as a woman can make your own list of conquests is a good one.

  2. Hi. I like what you have done with this site. This is quite funny – reading so many different interpretations of songs – and I mean that in a nice way. I appreciate that millions of Bob Dylan fans have an opinion on this and that
    and that and this (the above is typical of that.)

    This is a mocking song.
    Dylan was very cruel towards her.
    Making fun of her shopping habits and new purchases – which
    were totally unbelievable for New York in 1964 and 1965 – in this case her hat. But it was not just the hat.
    The point ?
    This song is about Edie Sedgwick.


  3. balances on head like a mattress balances on a bottle of wine
    drunken sex by a pin head, u cant balance a mattress on a bottle of wine
    she is criticized for like of thinking and being sexually indulgent. a drunk to boot

  4. The song is genius and it is about attachments and the fetishism they give rise to

  5. i have heard that dylan had a brief affair with jackie kennedy and we all know her love of pill box hats. but im not sure if that could be the meaning because of the timing of release and the presidency.

  6. You guys! This is just a fun witty romp that you can dance to! The Bob has a great sense of humor, God bless him!!!

  7. But I do love the theory of Bob having an affair with Jackie! Can’t you just see them, arm in arm in their big sunglasses (Jackie in her leopard skin pillbox hat), aka that album cover (the Free Wheeling Bob Dylan)?

  8. Hello Tony, thank you for another interesting analysis of a song from Bob Dylan’s Music Box. Lift the lid and join us inside to listen to every version of every song composed, recorded or performed by Bob Dylan, plus all the great covers and so much more.

  9. I’m with you. Jackie was mom in law’s customer at Ben Kahn Furs. Old Man Kahn cut the leopard skin for THAT hat and Lenore Marshall made it. I got married in 1969 and Lenore made my headpiece which was a small pillbox hat with the tulle attached to it. I always thought the song was about Jackie too!

  10. Yes, Hazard you r right: Edie sadly had difficulty with drugs, but she and Bob were lovers. Finally her preoccupation with her difficult life-though she came from a wealthy family-eventually broke them up.

  11. Jackie Kennedy wore pill-box hats in the early 1960s, and made them popular. So that’s that part.

    It’s 100 percent atmospheric, especially if you’ve heard Dylan play it over the past 10 years. Rockin’, opening-number blues.

  12. This is a blues song. Blues songs are about sex mainly and a little about drinking and less about the man.

    The metaphor is about the female sex bodily part, aka “box”. Of course
    , to use that word is not subtle and would be not in keeping with the blues pattern of using sly metaphors.


    Every verse is about sex, her sex, his desire for sex with her, after coital bliss, a friend (the doctor) cheating with her, and finally he catches her at it and her wants to her to know her new partner only cares about her leopard skin pillbox hat. That is either a compliment to her sexual skills or a mean spirited slur.

    By the way, like all blues songs we can enjoy it on many levels. I learned that performing LSPBH made people laugh, probably at the joke last verse.

    One day I was busking downtown. A good looking woman walked by wearing a leopard skin jacket and matching pillbox hat. True. She gave me a sly wink and kept on walking. I will never forget that day.

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