3. Billy Ray Cyrus, 'Achy Breaky Heart'
Billy Ray Cyrus was just 20 years old when "Achy Breaky Heart" turned him into a country superstar. The song was a huge crossover hit that introduced line-dancing to people all across the globe. A hit like that should have forever destroyed Billy Ray's career, but he started acting in the early 2000s – and in 2005 his daughter Miley landed the role of Hannah Montana and Billy Ray was cast as her father. He's now a TV icon to teenagers all across the country, most of whom have probably never heard "Achy Breaky Heart."