Conversation so far:
How can the lyrics of Cross Road Blues be interpreted?
In the simplest reading, Johnson describes his grief at being unable to catch a ride at an intersection before the sun sets.
Why would Johnson grieve over being unable to catch a ride?
He expresses apprehension at being stranded as darkness approaches.

Question: Did he at some point want to be picked up?
Self-contained rewrite: Did Johnson at some point want to be picked up in the cross road blues?