From a Brooks and Dunn song "Hillbilly Deluxe". Coon Smile refers to a raccoon smile. When a raccoon smiles it looks a little cute, but a little devious at the same time. No racial references are applied to "Coon Smile"
Couple Kids, Sweet thing driving a fastback
Shoot em Coon smile
Hoping that they smile back.
a smile a black person gives to try to catch the attention of the "ladiez"
"i flash her a coon smile and hope she smiles back"- brooks and dunn