The songs were written by Earle with musical accompaniment provided by the famous bluegrass band of Del McCoury.
The album was a significant departure from Earle's previous work, being the first wholly bluegrass album he had written. Earle made the album as a tribute to the founder of bluegrass music, Bill Monroe, who had died in 1996.
The album was nominated for a 2000 Grammy Award in the "Best Bluegrass Album" category (Earle's seventh Grammy nomination). Two tracks from the album were released as singles in the UK: "Dixieland" (distributed to radio only) and "The Mountain" (a commercial release).