Dan Tyminski

From Discogs:

Dan provided the singing voice for George Clooney in the Coen Brothers film O Brother, Where Art Thou? He is a guitarist and vocalist as part of the Bluegrass band Union Station, which he became a member of in 1994. He is a former member of the Lonesome River Band, for which he was also vocalist as well as playing the mandolin. As well as playing with Alison Krauss & Union Station, Dan is a solo artist in his own right, having released his first album in 2000, as well as being an in-demand session player.

From Lastfm:

Dan Tyminski (b. June 20, 1967) is a bluegrass composer, vocalist, and instrumentalist. He is a member of the band Alison Krauss and Union Station and has released a solo album entitled Carry Me Across the Mountain (2000) on the Doobie Shea Records label. He is likely best known for the song "Man of Constant Sorrow," which was featured in the movie O Brother, Where Art Thou? and won the 2001 CMA award for best single as well as a Grammy Award for best Country Collaboration with Vocals (along with Harley Allen and Pat Enright, filling out the vocals for the movie's Soggy Bottom Boys).

Read more about Dan Tyminski on Last.fm.

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From Wikipedia:

Daniel "Dan" Tyminski (born June 20, 1967 in Rutland, Vermont) is a bluegrass composer, vocalist, and instrumentalist. He is a member of the band Alison Krauss and Union Station and has released a solo album entitled Carry Me Across the Mountain (2000) on the Doobie Shea Records label.

He is best known for his updated version of the song "Man of Constant Sorrow," which was featured in the movie O Brother, Where Art Thou? and won the 2001 CMA award for best single as well as a Grammy Award for best Country Collaboration with Vocals (along with Harley Allen and Pat Enright, filling out the vocals for the movie's Soggy Bottom Boys). In total, he has won 10 Grammy awards for solo and collaborative projects.