19 wins & 77 nominations
2011 Nominee Grammy- Best Country Vocal Performance - Male
For the song "Cryin' For Me (Wayman's Song)."- 2005 Nominee Grammy
- Best Country Collaboration with Vocals
For the song "Pancho & Lefty"Shared with: Merle Haggard · Willie Nelson - 2004 Nominee Grammy
- Best Country Collaboration with Vocals
For "Beer For My Horses"Shared with: Willie Nelson
- 2012 Nominee Blimp Award
- Favorite Male Singer
- 2014 Nominee People's Choice Award
- Favorite Country Music Icon
- 2013 Nominee ACM Award
- Male Vocalist of the Year
- 2012 Nominee ACM Award
- Single Record of the Year
For "Red Solo Cup"Shared with: Mark Kalbfeld · Michael Salomon
- 2005 Nominee CMA Award
- Entertainer of the Year
- 2007 Nominee American Music Award
- Favorite Country Male Artist
- 2006 Winner American Music Award
- Favorite Country Male Artist
- 2005 Nominee American Music Award
- Artist of the Year
- 2005 Nominee American Music Award
- Favorite Country Male Artist
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