John D. Loudermilk wrote this song and originally recorded it in 1960. He was born and raised in the old tobacco warehouse city of Durham, North Carolina, and this is a somewhat autobiographical song about the city. Loudermilk was a prolific composer of many styles, and his songs ("Then You Can Tell Me Goodbye," "Big Daddy," "Paper Tiger," "Break My Mind," "Indian Reservation") have been covered by many different artists.
Loudermilk (from American Songwriter Magazine January/February 1988): "I got the idea for writing that song from a road in our town that was called Tobacco Road because it was where they rolled the hogsheads full of Tobacco down to the river to be loaded onto barges. Along that road were a lot of real tough, seedy-type people, and your folks would have just died if they thought you ever went down there."
The Nashville Teens were most certainly not from Nashville: they were part of the British Invasion and gave themselves an American name so it would be less obvious that they were from England. It worked, at least for this song, as they had a hit with it four years after Loudermilk originally recorded it. One member of The Nashville Teens, Michael Dunford, became a mainstay with the classical rock band Renaissance as a guitarist and primary songwriter. Dunford died from a cerebral hemorrhage in 2012 at age 68.
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