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My favourite hit single of all time is probably Pink Floyd's 'See Emily Play', written by Syd Barrett.
The song is named after Emily Young, at one time a close friend of Syd's. Speaking on the recent BBC documentary 'Psychedelic Britannia', she offered the opinion that the girl described in the lyrics was Syd himself. Given that so many of his other compositions are rooted in memories of his childhood, it seems possible that Syd may have been expressing more than just his feminine side.
Put on a gown that touches the ground...