Public interest in the song was renewed after the release of the 2000 film '' O Brother , Where Art Thou ? '' , where it plays a central role in the plot . The song , with lead vocal by Dan Tyminski , was also included in the film 's highly successful , multiple-platinum-selling soundtrack . This recording won a Grammy for Best Country Collaboration at the 44th Annual Grammy Awards in 2002
44th Annual Grammy Awards
44th Annual Grammy Awards
Man of Constant Sorrow