Nobody writes spiteful songs as well as Bob Dylan. One of his better ones is “Leopard-Skin Pill-Box Hat”, a rare pop song with two hyphenated words in its title. Recorded in 1966 for Blonde on Blonde, the song was released as a single in March 1967, a few weeks before the release of his first Greatest Hits album (which doesn’t include this song – strange marketing, that).
The song combines an interest in the already then out-of-style pill-box hat made famous by Jackie Kennedy, with leopard-skin, which was no more classy in 1967 than it is today. It’s a classic Dylan put down song:
Well, I see you got a new boyfriend
You know, I never seen him before
Well, I saw him
Makin’ love to you
You forgot to close the garage door
You might think he loves you for your money
But I know what he really loves you for
It’s your brand new leopard-skin pill-box hat
Wikipedia and other sources claim that the song is about Edie Sedgwick. Could be – I couldn’t tell you. That claim is part of a larger concern among Dylanologists to determine what every reference in every lyric could possibly mean. I have to say, these concerns are not generally mine. I don’t really care who Dylan was singing about – I don’t even care if it was a single person that inspired a song like this one. For me it’s much more the fact of the vitriol, and even if this song is a pale shade of something like “Positively 4th Street”, I am still amused by the bitterness that Dylan enabled to fill the pop charts.
This was Dylan’s only single released in the US in 1967. John Wesley Harding came out in the last week of December, and its singles (“Drifter’s Escape” and “All Along the Watchtower” came out in 1968). It’s a pretty minor effort all things considered.
Here’s a good version from London at the end of the 1966 tour: