6 wins & 40 nominations
- 1999 Winner Grammy
- Best Country Collaboration with Vocals
for "Same Old Train"Shared with: Dwight Yoakam · Randy Travis · Pam Tillis · Marty Stuart · Ricky Skaggs · Earl Scruggs · Patty Loveless · Alison Krauss · Emmylou Harris · Merle Haggard · Joe Diffie · Clint Black - 1997 Nominee Grammy
- Best Country Collaboration with Vocals
For "Hope: Country Music's Quest For A Cure" - 1997 Nominee Grammy
- Best Country Collaboration with Vocals
For "Honky Tonkin's What I Do Best"Shared with: Marty Stuart - 1995 Nominee Grammy
- Best Country Vocal Collaboration
For "The Devil Comes Back To Georgia"Shared with: Johnny Cash · Marty Stuart - 1994 Nominee Grammy
- Best Music Video, Long Form
For "A Celebration - A Musical Tribute To The Spirit Of The Disabled American Veteran"
- 2002 Nominee ACM Award
- Top Male Vocalist
- 2002 Nominee ACM Award
- Single Record of the Year
For "It's a Great Day to Be Alive"Shared with: Billy Joe Walker Jr. - 2002 Nominee ACM Award
- Vocal Event of the Year
For "Out of Control Raging Fire"Shared with: Emory Gordy Jr. · Patty Loveless - 1997 Nominee ACM Award
- Top Vocal Duet
- 1999 Nominee CMA Award
- Vocal Event of the Year
For "Same Old Train"Shared with: Earl Scruggs · Ricky Skaggs · Marty Stuart · Pam Tillis · Randy Travis · Dwight Yoakam · Clint Black · Joe Diffie · Alison Krauss · Patty Loveless · Merle Haggard · Emmylou Harris - 1996 Nominee CMA Award
- Vocal Event of the Year
For "Honky Tonkin's What I Do Best"Shared with: Marty Stuart - 1994 Winner CMA Award
- Album of the Year
For "Common Thread: The Songs of the Eagles"Shared with: Vince Gill · Alan Jackson · Little Texas · Lorrie Morgan · Tanya Tucker · Trisha Yearwood · John Anderson · Clint Black · Suzy Bogguss · Brooks & Dunn · Billy Dean · Diamond Rio · Tony Brown · Don Cook · Jerry Crutchfield · Christy DiNapoli · Garth Fundis Jonathan · Doug Grau · Scott Hendricks · Richard Landis · Lynn Peterzell · Monty Powell · Keith Stegall · James Stroud - 1994 Nominee CMA Award
- Album of the Year
For "Rhythm, Country & Blues"Shared with: The Staple Singers · Chet Atkins · Marty Stuart · Allen Toussaint · Tanya Tucker · Conway Twitty · Vince Gill · Clint Black · Reba McEntire · Sam Moore · George Jones · B.B. King · Gladys Knight · Patti LaBelle · Al Green · The Pointer Sisters · Aaron Neville · Lyle Lovett · Trisha Yearwood · Natalie Cole · Don Was
- 2002 Nominee American Music Award
- Favorite Country Male Artist
- 1992 Nominee American Music Award
- Favorite Country Song
For the song "Here's a Quarter (Call Someone Who Cares)" - 1991 Nominee American Music Award
- Favorite Country New Artist
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