Keith Urban is one of the biggest country stars of his generation, but things weren't always so rosy when he first came to Nashville.

Urban moved to Music City in 1992, after releasing one album in his native Australia. He got several cuts as a writer, and in 1997 he formed the Ranch, a rock-influenced country group. They released one album for Capitol Records and charted two singles; "Walkin' the Country" and "Just Some Love."

Despite their minor chart successes, the period when he was in the Ranch marked a tough time for Urban.

“The Ranch was a mess, period, because we were in a s--t van going all over the country playing to three people. It was soul sucking to the ultimate degree,” he recalls.

Though they didn't score any lasting success, their songs live on. The Dixie Chicks recorded "Some Days You Gotta Dance" for their Fly album (with Urban guesting on lead guitar), and Steel Magnolia revived "Homespun Love" in 2011. David Nail recorded "Desiree" in 2011, and Scotty McCreery covered "Walkin' the Country" on his 2012 debut album.

Urban stayed signed to Capitol when the Ranch came to an end, and he released his self-titled stateside debut album in 1999, scoring four hits, including his first No. 1 hit, "But for the Grace of God." He took home Top New Male Vocalist honors at the 2001 Academy of Country Music Awards and won the 2001 CMA Horizon Award, setting him on the road to a career as one of the best-selling and most awarded country singers of his generation.

You've Never Seen "Up Down" Singer Morgan Wallen Like This: 

See Country Stars' Yearbook Photos

More From Taste of Country