“HE KEPT RIDING… EVEN WHEN HIS HEART BEGGED HIM TO STOP.”Waylon Jennings had a way of singing that felt like he was letting you peek behind a tough man’s curtain. “All Around Cowboy” is one of those songs. You can almost see him — dust on his jacket, hands still shaking after a long ride — trying to convince the world he’s fine. But the truth sits quietly in his voice. A man can chase one more town, one more arena, one more win… and still feel the empty seat beside him. Waylon sings that kind of honesty — the kind you only share when the lights go out and the road gets quiet.
“HE KEPT RIDING… EVEN WHEN HIS HEART BEGGED HIM TO STOP.” Waylon Jennings had a gift most singers spend a…