The best known and, possibly, the most over-analyzed song in Syd Barrett's entire catalog, "Octopus" can be absorbed upon a multitude of different levels. Not only did it lend plausibly pertinent lyrics to the titles of both Barrett's first solo album (The Madcap Laughs and his best biography (Julian Palaicos' Lost In The Woods, its tongue-twisting wordplay and helter-skelter imagery have also been interpreted as everything from an echo of the carnival backdrop to the Beatles' Sgt Pepper, to a self-diagnosis of the psychiatric malaise that eventually drove Barrett from the public eye.
Work on "Octopus" commenced on July 20 1968, when Barrett and producer Dave Gilmour made the first stab at what was then titled "Clowns And Jugglers". The first take is included in the Opel portion of the Crazy Diamond box set, and is rudimentary in the extreme, Barrett's voice a rough yowl and the lone electric guitar a dark mélange of haunted chords, jagged clangs and spacey effects - isolate the instrumentation alone and you could be listening to a formative "Interstellar Overdrive".
The ten months that separated these sessions from Barrett's next studio sojourn saw the song undergo considerable revision, although only after an attempt to flesh out the earlier performance with military drum and piping organ overdubs was abandoned. (Applied to the original second take from July, this version was featured on the original Opel out-takes collection). Finally, on June 13, opening the penultimate sessions for the LP, the familiar version of "Octopus" began to take shape, spread over eleven takes (including several false starts). The first two of these appear within the Madcap portion of the Crazy Diamond box set, the last - fulsomely overdubbed - was retained for the LP itself, and also made it out as a UK single in December 1969.