| Award | Category | Year |
| CMA | Entertainer of the Year | 1998 |
| Academy of Country Music | Entertainer of the Year | 1998 |
| Grammy | Best Country Collaboration With Vocals | 1997 |
| CMA | Entertainer of the Year | 1997 |
| American Music Awards | Favorite Male Artist | 1997 |
| Academy of Country Music | Entertainer of the Year | 1997 |
| Academy of Country Music | Special Achievement Award | 1997 |
| American Music Awards | Favorite Album | 1996 |
| American Music Awards | Favorite Male Artist | 1996 |
| American Music Awards | Favorite Male Artist | 1995 |
| American Music Awards | Favorite Male Artist | 1994 |
| Academy of Country Music | Jim Reeves Memorial Award | 1994 |
| Academy of Country Music | Video of the Year | 1994 |
| ASCAP | Songwriter of the Year | 1994 |
| CMA | Vocal Event of the Year | 1993 |
| American Music Awards | Favorite Male Artist | 1993 |
| Academy of Country Music | Entertainer of the Year | 1993 |
| Academy of Country Music | Video of the Year | 1993 |
| ASCAP | Songwriter of the Year | 1993 |
| TNN/Music City News | Entertainer of the Year | 1992 |
| CMA | Album of the Year | 1992 |
| CMA | Entertainer of the Year | 1992 |
| American Music Awards | Favorite Album | 1992 |
| American Music Awards | Favorite Male Artist | 1992 |
| American Music Awards | Favorite Single | 1992 |
| Academy of Country Music | Entertainer of the Year | 1992 |
| TNN/Music City News | Video of the Year | 1991 |
| Grammy | Best Male Country Vocal Performance | 1991 |
| CMA | Album of the Year | 1991 |
| CMA | Entertainer of the Year | 1991 |
| CMA | Music Video of the Year | 1991 |
| CMA | Single of the Year | 1991 |
| American Music Awards | Favorite Single | 1991 |
| Academy of Country Music | Entertainer of the Year | 1991 |
| Academy of Country Music | Top Male Vocalist | 1991 |
| CMA | Horizon Award | 1990 |
| CMA | Music Video of the Year | 1990 |
| Academy of Country Music | Album of the Year | 1990 |
| Academy of Country Music | Entertainer of the Year | 1990 |
| Academy of Country Music | Single of the Year | 1990 |
| Academy of Country Music | Song of the Year | 1990 |
| Academy of Country Music | Top Male Vocalist | 1990 |
| Academy of Country Music | Video of the Year | 1990 |
