Robert Johnson is the dude I'm most concerned with here because of his place in rock history (stupid Rolling Stone lists aside). He was the third member of Club 27 (after Alexandre Levy and Louis Chauvin) when he died probably of strychnine poisoning in 1938. The legend of his meeting with The Gentleman was around in his lifetime (can you imagine trying to deny something like that?) and has been filmed and written about by Martin Scorcese, Japanese Magna artist Akira Hiramoto and Native American writer Sherman Alexie (Reservation Blues is awesome) among others. The lyrics (the links in the song titles will take you to the lyrics) of "Cross Road Blues" are fearful but the fear is probably of being lynched for breaking the curfew imposed on African-Americans in parts of the South at the time rather than meeting the devil, as discussed here. Robert did sing about feeling chased by something demonic in "Hellhound On My Trail."
While Robert Johnson denied ever meeting Old Scratch, Tommy Johnson ran with it. The Tommy Johnson character in O Brother, Where Art Thou? is based on him. According to wikipedia he "cultivated a sinister persona," and, really, how much more sinister can you get? Tommy was an alcoholic and sang about drinking Sterno in "Canned Heat Blues." It was a common practice during the Prohibition and Depression. My brilliant Chemist husband explained to me that methanol is added to products (including Sterno) containing ethanol (grain alcohol) to make them unpalatable. Trusty wikipedia says that "as little as 10 mL of pure methanol can cause permanent blindness and...30mL is potentially fatal" with "toxic effects tak[ing] hours to start." I can imagine few surer signs that a devil really does have a grip on your soul than trying to get high from filtering Sterno through a sock or cheesecloth and then mixing it with juice. Think about the craving in your body it would take that you'd risk blindness or death to satisfy it. Tommy died in 1956 of a heart attack that was probably related to his alcoholism.
I have to say that while I'd heard "Canned Heat Blues" maybe twice or three times before preparing this post I've listened to it non-stop while writing this. The desperation in his voice is the truest thing I've heard in a long while. Just to let you know, we'll be having another visit with Old Scratch this week so prepare yourself and have a great Monday.
Edit: Because I'm so familiar with this legend I made the assumption that everyone is but I've gotten a couple of messages about it so for clarification it goes like this:
Robert (or Tommy) Johnson wanted to be a great bluesman but practice though he might he wasn't getting any better. He heard about a way to become the greatest ever but it would cost him his soul. He thought about it for a while and one night, fortified by some whiskey, he went to The Crossroads at midnight and waited. In a few minutes The Gentleman (the Devil) stepped out of the tall grass, tuned Johnson's guitar, played a few songs and handed the guitar back and disappeared. Johnson went on the record the music that became the bedrock of blues and rock music. It's related to other Faustian legends but I doubt those legends have giant kitchy memorials marking the spot where they're said to have happened.
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