With his steamy good looks and painted-on jeans, muscley, mulletted country newcomer Billy Ray Cyrus came out of nowhere with a hit that catapulted him to superstardom. But he and his butt also became the butt of many, many jokes. Still, if his 1992 crossover smash, “Achy Breaky Heart,” is widely regarded as one of the cheesiest songs of all time, its music video transformed line dancing into a global sensation, and turned legions of top 40 listeners on to a genre they’d previously dismissed.

In this episode, we delve into Cyrus’ complicated legacy, the lasting influence of his notorious hairstyle, and how he had the last laugh when he returned to the pop charts nearly three decades later to break records and once again flip the world of country upside down.