One of Drake's very few linear lyrics, in this one he basically chides himself for his own indomitable despair. Much of the Bryter Layter album follows a similar theme, including probably the best known song from it, "One of These Things First."
South African jazz musician, Chris McGregor, recorded his incredible piano for this track in just one take. McGregor is perhaps best-known for founding and leading the South African sextet, The Blue Notes.
The producer, Joe Boyd, seized upon the jazzy song's cloaking of self-pity in self-mockery in an arrangement that featured a Greek chorus sung by PP Arnold and Doris Troy. Nick Drake wasn't very happy with the way his song had turned out. Boyd recalled to Mojo: "On his original demo of 'Poor Boy,' Nick sang the line, 'Oh poor boy. So sorry for himself,' mocking himself. The minute I heard that I thought of emulating the mocking female voices on Leonard Cohen's 'So Long, Marianne.' Nick said, 'Do you think so?' and in retrospect I think that may have been him saying, 'I don't think so.'"
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