Bob Dylan Blues | 1965, Handwritten Syd Barrett letter with the lyrics to one of his first songs & a self portrait doodle.

A letter to Syd Barrett's first girlfriend, written before his fame with Pink Floyd, containing the handwritten lyrics to his first known song, and a self-portrait doodle. Written the same summer Dylan was recording Highway 61 Revisited.

The Dylan reference is no accident. Barrett wrote "Bob Dylan Blues" after seeing Dylan in London and as a wry response to the prevailing fashion for Dylan imitators on the mid-1960s London scene. The song was recorded in the 1970s after Syd had left Floyd and was then forgotten until David Gilmour unearthed the tape in his personal collection. It was released in 2001 on the Barrett compilation The Best of Syd Barrett: Wouldn't You Miss Me?.

The letter is simultaneously five things: a deeply personal letter, a reference to Dylan by name, the lyrics to his first known song, an original self-portrait, and a window into the surreal mind of a reclusive genius as his creative career began. Nothing comparable has appeared on the open market.

The letter also has a doodle of Syd's head in a puddle. This is a holy grail item for Pink Floyd and Syd Barrett collectors.

Writing to his girlfriend Jenny Spires, later immortalised as “Jennifer Gentle” in “Lucifer Sam”, Barrett declares:

“I have written a song about Bob Dylan. Yeh! Yeh! Soul. God. etc. It starts off:

‘I got the Bob Dylan blues
And the Bob Dylan shoes
And my hair an’ my clothes in a mess,
But you know I just couldn’t care less.’”

He describes the song as “a bit satirical and humorous”, followed by the characteristically playful “Ho! Ha! Hee! Tee!”

The remaining text is equally revealing. Barrett worries that Jenny’s letters make it sound as though she does not “care a bugger” and admits that he has never actually asked whether she wants to go out with him. He then writes:

“Pause while I slip into a large puddle of self pity on the floor.”

Beneath this, Barrett draws a broad puddle containing a small, heavily inked head, identified by an arrow and the caption “My head.”

Provenance: Jenny Spires, the recipient of the letter; from her personal collection.

Autograph letter to Jenny Spires containing the earliest known surviving handwritten text of a Syd Barrett song. Early 1965. Two pages in blue ballpoint, signed “Syd”, with an original self-portrait doodle. Original horizontal folds and light handling creases, otherwise well preserved and entirely legible.