"Man of Constant Sorrow" is certainly the most unexpected hit of the 21st century. The fictional Soggy Bottom Boys gave country fans and country radio this gift. During O Brother Where Art Thou? they perform it twice, including the film’s dramatic, comedic conclusion that you really need to re-watch if it’s been a few years.

No, George Clooney did not sing on this song or during the movie. Singer and Alison Krauss bandmate Dan Tyminski is the real man behind the song, a Top 40 radio hit and CMA and Grammy winner. As a soundtrack, the O Brother Where Art Thou? album sold over eight million copies and is regularly ranked as one of the best or most important albums of the decade, century or of all time.

“It was released in the middle of a very non-bluegrass part of country music, era of country music, and it cut right through like a knife,” Joe Nichols recalls of the 2001 hit. “It sounded old, but it sounded new and I think it just grabbed everybody.”

Song No. 21 on our Top Country Songs of the Century list is the only bluegrass song, the only non-radio hit and the only song from a soundtrack. It’s also the only song from a fictional group. Fans and country music experts wasted no time in nominating this song through to the list during round one of discussions.

About this list: Taste of Country’s Top Country Songs of the Century were decided by a panel of country music experts and fans using sales and chart data, a song’s social and musical impact and lyrical integrity. Select artists were also surveyed. You’ll hear from several throughout the list.

Joe Nichols Explains the Importance of "Man of Constant Sorrow"