5 wins & 16 nominations
- 2019 Winner Grammy
- Best Country Song
For song "Space Cowboy" artist: Kacey MusgravesShared with: Shane McAnally · Kacey Musgraves - 2015 Nominee Grammy
- Best Country Song
For the song "American Kids."Shared with: Rodney Clawson · Shane McAnally - 2015 Nominee Grammy
- Best Country Song
For the song "Give Me Back My Hometown."Shared with: Eric Church - 2014 Winner Grammy
- Best Country Album
For the album "Same Trailer Different Park."Shared with: Kacey Musgraves
- 2019 Nominee ACM Award
- Song of the Year
For "Space Cowboy"Shared with: Kacey Musgraves · Shane McAnally - 2017 Nominee ACM Award
- Songwriter of the Year
- 2016 Winner ACM Award
- Vocal Event of the Year
For event "Smokin' and Drinkin'Shared with: Miranda Lambert · Little Big Town · Natalie Hemby · Shane McAnally · Frank Liddell · Chuck Ainlay · Glenn Worf - 2015 Winner ACM Award
- Songwriter of the Year
- 2015 Nominee CMA Award
- Album of the Year
For "Pageant Material"Shared with: Shane McAnally · Kacey Musgraves - 2015 Nominee CMA Award
- Song of the Year
For "American Kids"Shared with: Rodney Clawson · Shane McAnally - 2013 Nominee CMA Award
- Album of the Year
For "Same Trailer Different Park"Shared with: Kacey Musgraves · Shane McAnally - 2013 Nominee CMA Award
- Single of the Year
For "Merry Go 'Round"Shared with: Kacey Musgraves · Shane McAnally
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