Yeah, I know … John Mellencamp‘s from Indiana, which isn’t one of the Route 66 states.
But he was born and raised in a small town, and his 1985 hit song by the same name (back when he still partly used his John Cougar stage name) captures the humility and pride of small-town people better than any I can think of. He gets the feel right.
And since Route 66 is frequently described as the world’s longest small town,” Mellencamp’s tune seems appropriate here.