Gray was born James Dixon, in Somerville, Texas. He spent the latter part of his life performing and busking folk, blues and gospel music at Chicago's Maxwell Street flea market and at rapid-transit depots. In the 1960s, he recorded two singles for his own Gray label, including "Freedom Rider" backed with "Freedom Bus."
Gray's only album, The Singing Drifter (1973), was reissued on the Conjuroorecord label in 2005. The reissue was produced by Cary Baker, who wrote the liner notes for the original vinyl LP, released by Birch Records.
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