As one of the biggest country singers of the 90s, John Michael Montgomery's sophomore album Kickin' It Up just might be his best. Or is it? We debate that and many other things this episode including which artist today would be best suited to cover one of his songs? Names like Michael Ray and Jon Pardi were suggested including another 90s country artist.

The album featured his biggest hit to date with "I Swear." Top hits "Be My Baby Tonight" and "If You've Got Love" reached the #1 spot on the charts while another Montgomery staple "Rope the Moon" went all the way to #4.