Country music star Kenny Chesney pretends that wearing a brand-new black cowboy hat is the most normal and natural thing in the world. This was during his performance live on the fall concert series of the TV show Good Morning America in New York City on October 14, 2008. Kenny Chesney was born in 1968, so he turned 40 the year this photo was taken. Did he imagine when he was a child that as he entered his fifth decade, he'd be wearing a cowboy hat in a performative manner? Probably not.