Leopard-Skin Pill Box Hat (1966) – Bob Dylan (Live 1966)

Bob Dylan is obsessed with his ‘honey’s’ Leopard-Skin Pill Box Hat. So much so he asks her: Honey, can I jump on it sometime? Yes, I just wanna see If it’s really the expensive kind.
If I had a gal who owned a Leopard-Skin Pill Box Hat (like a dreamy Audrey); I too would be obsessed and fancy jumping on it, to the point where a doctor might suggest Audrey (‘that lass in your dreams‘) is bad for your health. It goes without saying: ‘I wouldn’t act on his advice’.

Leopard-Skin Pill Box Hat is the third song to appear here from from the legendary Manchester Free Trade Hall 1966 concert. I wrote about Edward Norton’s comments of Dylan’s impact on the music scene and the immensity of this concert.

Oh, you like what I’m doing? I’m gone..I’m over here..’enjoy’…You’re not gonna like it because you liked what I just did and now where I’m going you are going to be discombobulated and upset and eventually, you’re going to catch up and when you catch up, I’m going to move onto something else.

How many people do you know, in any of the things we all do, who get a taste of a thing and don’t lean into it for a while? Who don’t think…’well this feels good’. May be I’ll just hang-out right here.

Leopard-Skin Pill Box Hat was first recorded here, one month prior to its official release on the mercurial new-rock record Blonde on Blonde.

[Verse 1]
Well, I see you got your
Brand new leopard-skin pillbox hat
Yes, I see you got your
Brand new leopard-skin pillbox hat
Well, you must tell me, baby
How your head feels under something like that
Under your brand-new leopard-skin pillbox hat

[Verse 2]
Well, you look so pretty in it
Honey, can I jump on it sometime?
Yes, I just wanna see
If it’s really the expensive kind
You know it balances on your head
Just like a mattress balances
On a bottle of wine
Your brand new leopard-skin pillbox hat

Leopard-Skin Pill-Box Hat peaked at number 81 on the American Billboard Top 100 chart.

According to Dylan’s lyrics, Wikipedia states that he affectionately ridicules a female “fashion victim“who wears a leopard-skin pillbox hat. The pillbox hat was a fashionable ladies’ hat in the United States in the early to mid-1960s, most famously worn by Jacqueline Kennedy. Dylan satirically crosses this accessory’s high-fashion image with leopard-skin material, perceived as more downmarket and vulgar. The song was also written and released after pillbox hats had been at the height of fashion.

Some journalists and Dylan biographers have speculated that the song was inspired by Edie Sedgwick, an actress and model associated with Andy Warhol. It has been suggested that Sedgwick was an inspiration for other Dylan songs of the time as well, particularly some from Blonde on Blonde. Following her estrangement from Warhol’s inner circle, Sedgwick began living at the Chelsea Hotel, where she became close to Bob Dylan. Dylan and his friends eventually convinced Sedgwick to sign up with Albert Grossman, Dylan’s manager.

1. Leopard-Skin Pill-Box Hat – Wikipedia

“The more I live, the more I learn. The more I learn, the more I realize, the less I know.”- Michel Legrand

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Posted in Music
15 comments on “Leopard-Skin Pill Box Hat (1966) – Bob Dylan (Live 1966)
  1. I had forgotten about those pill box hats!

  2. Badfinger (Max) says:

    I love anything live with Bob in 1966. Edie Sedgwick has always facsinated me…have you ever seen the movie Ciao Manhattan? It would not win any awards but it shows her decline with her in the lead role.

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