There was another thread on this several months ago, I will find and refresh it. Also an article on the Mudcat homepage, check there.

My two cents worth: It was Tommy Johnson, who may or may not have been related to Robert, who bragged that he sold his soul to the devil in exchange for guitar talents. More likely, he just went from Jackson up to Dockery's Plantation, spent some time learning songs from Charlie Patton, Willie Brown, and Son House, and when he returned he repeated a local folk belief to titillate his fans.

Robert's song "Crossroad Blues" which many say is an account of the soul-selling, if taken at face value has nothing more ominous than failure at hitch-hiking in it. Actually it's probably his most religious song because at least he prays for salvation in it.

His "Me and the Devil Blues" adds wife-beating to his list of sins, but was probably written to get a rise out of the local preacher. That song, and "Hellhound on my Trail", seem to me to be the work of a man who must have had a religious upbringing, then rejected it, and was suffering from a lot of guilt as a result.

How good was he? He certainly seems to have had an emotional life and he puts that emotion through pretty well on his records. He was blessed with a high pitched but still very masculine voice that is hard to equal or even mimic. As a guitarist, he was as good as anyone on the Delta I suppose, but there were others from other areas who I would judge to be superior - Blind Blake, Blind Willie McTell, Rev. Blind Willie Johnson for instance (although it's hard to judge because of the difference in style). Certainly there are modern guitarists such as John Hammond who can play rings around him technically--but still, I'd rather listen to "Poor Bob", if you please.