Throughout centuries of European mythology, crossroads were viewed as gathering places for evil demons and witches.
As a general literary symbol, crossroads often represent challenge and transition. To be "at a crossroads" is to be at a difficult point where you need to make a decision.
Because they mark a transition, crossroads in many cultures have been convenient places for communication between this world and other worlds. In the Christian tradition, this kind of communication meant something dangerous: ghosts, witches and demons might stop you at a crossroads. But in some African and South American traditions, crossroads were sites for a more positive kind of communication: a person could go to the crossroads to commune with the spirits or deities, or connect with the afterlife. In the Haitian Voodoo tradition (a melding of indigenous African traditions with the Catholic beliefs forced on them by French slave owners), crossroads have their own deity, Papa Legba. In every case, the crossroads are a place where the veil between this world and the next is especially thin.
"Cross Road Blues" is frequently represented as Johnson's own record of meeting Satan at a crossroad, but the only figure Johnson seems to meet at that imagined Mississippi intersection is God.
As the story goes, Johnson goes to a crossroads at midnight. There he meet a large man, the devil, who taps on his shoulder. Without turning around, Johnson hands over his guitar and waits in a dark silence. The devil tunes Robert's guitar for him in exchange for a small token—his soul. From then on Johnson can play the blues like no one else, but he is pursued by hellhounds and haunted with nightmares. His tragic young death is the devil's way of showing who's boss without breaking the agreement.
But in this key line in the song that is so central to the story, Johnson doesn't seem to be talking to the devil. Completely contradicting the whole story, Johnson is talking to God, asking for mercy and advice about a way to go forward—presumably from a difficult time in his life. It lends itself to a different interpretation than the wisdom of folklore suggests.
Willie Brown was a blues guitarist who mentored Johnson—before Johnson went to the crossroads, that is. Who needs a mentor if you have a satanic pact?
Around 1930, when Willie Brown and great guitarist Son House were in Robinsonville, Mississippi, trying to make a name for themselves, a very young Johnson used to hang around playing their guitars in between sets and irritating audiences with his mediocrity. In 1965, House called Johnson a "little boy" who hung around the bluesmen trying to get a piece of the action. At least according to House, the teenage Johnson was a nuisance at best. It apparently wasn't until he disappeared off the scene for a while that the "little boy" Robert Johnson became an unbelievably capable guitar player, able to imitate almost anything he heard on the radio and perform musical styles ranging from swing to Irish folk. This mysterious and quick transition observed by those around him later added to the apparent legitimacy of the devil legend. Without satanic support (so the logic goes), how could Johnson have gone from nuisance to genius seemingly overnight?