3 wins & 11 nominations
- 2019 Nominee Oscar
- Best Achievement in Music Written for Motion Pictures (Original Song)
For song "When a Cowboy Trades His Spurs for Wings"Shared with: David Rawlings
- 2018 Nominee Grammy
- Best American Roots Song
For the song "Cumberland Gap" artist: David RawlingsShared with: David Rawlings - 2012 Nominee Grammy
- Best Folk Album
For the album "The Harrow & The Harvest."Shared with: David Rawlings - 2002 Winner Grammy
- Album of the Year
Shared with: Alison Krauss · Union Station · Tim Blake Nelson · Chris Thomas King · Emmylou Harris · Harley Allen · John Hartford · Norman Blake · Pat Enright · Hannah Peasall · Leah Peasall · Sarah Peasall · Ralph Stanley · Sam Bush · Stuart Duncan · The Cox Family · The Fairfield Four · The Whites · T Bone Burnett · Peter F. Kurland · Mike Piersante · Gavin Lurssen · Jerry Douglas · Barry Bales · Ron Block · Dan Tyminski · Cheryl White · Sharon White - 2002 Nominee Grammy
- Best Country Collaboration with Vocals
For "Didn't Leave Nobody But The Baby"Shared with: Alison Krauss · Emmylou Harris
- 2019 Nominee World Soundtrack Award
- Best Original Song Written for a Film
for the song "When a Cowboy Trades His Spurs for Wings"
- 2019 Nominee Gold Derby Film Award
- Original Song
for "When a Cowboy Trades His Spurs for Wings"Shared with: David Rawlings
- 2001 Winner CMA Award
- Album of the Year
For "O Brother, Where Art Thou?"Shared with: The Whites · Norman Blake · The Fairfield Four · Emmylou Harris · John Hartford · James Carter and the Prisoners · Chris Thomas King · Alison Krauss · Harry McClintock · Hannah Peasall · Leah Peasall · Sarah Peasall · The Soggy Bottom Boys · The Stanley Brothers · Ralph Stanley · T Bone Burnett - 2001 Nominee CMA Award
- Vocal Event of the Year
For "Didn’t Leave Nobody But the Baby"Shared with: Emmylou Harris · Alison Krauss
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