As country music entered a new millennium, multiple stars of the 1990s added to their legacies. Indeed, some of 2000's better songs come to mind whenever anyone brings up Sara Evans, Jo Dee Messina, John Michael Montgomery, Travis Tritt and Lee Ann Womack.

Beyond defining moments for established names, the year introduced potential new stars ranging from a pre-teen Billy Gilman to Australian songwriter Jamie O'Neal. On the folksier side of the spectrum, Americana got arguably its biggest boost to date with an Emmylou Harris masterpiece and the most important country-related soundtrack since Urban Cowboy.

For perspective on how country music transitioned from one of its biggest decades to a new century, revisit these 10 albums that are turning 20 years old in 2020.