| Year | Awards |
|---|---|
| 1999 | American Music Awards Favorite Male Artist American Music Awards Favorite Album Country Music Awards Artist of the Decade |
| 1998 | American Music Awards Favorite Country Male Artist American Music Awards Favorite Country Album Academy of Country Music Special Achievement Award Academy of Country Music Entertainer of the Year Blockbuster Favorite Male Country Artist Grammy Best Country Vocal Collaboration Peoples Choice Award |
| 1997 | American Music Awards Favorite Male Artist CMA Entertainer of the Year |
| 1996 | American Music Awards Favorite Album American Music Awards Favorite Male Artist |
| 1995 | American Music Awards Favorite Male Artist |
| 1994 | ASCAP Songwriter of the Year Academy of Country Music Jim Reeves Memorial Award Academy of Country Music Video of the Year American Music Awards Favorite Male Artist |
| 1993 | ASCAP Songwriter of the Year Academy of Country Music Entertainer of the Year Academy of Country Music Video of the Year American Music Awards Favorite Male Artist CMA Vocal Event of the Year |
| 1992 | Academy of Country Music Entertainer of the Year American Music Awards Favorite Album American Music Awards Favorite Male Artist American Music Awards Favorite Single CMA Album of the Year CMA Entertainer of the Year TNN/Music City News Entertainer of the Year |
| 1991 | Academy of Country Music Entertainer of the Year Academy of Country Music Top Male Vocalist American Music Awards Favorite Single CMA Album of the Year CMA Entertainer of the Year CMA Music Video of the Year CMA Single of the Year Grammy Best Male Country Vocal Performance TNN/Music City News Video of the Year |
| 1990 | Academy of Country Music Album of the Year Academy of Country Music Entertainer of the Year Academy of Country Music Single of the Year Academy of Country Music Song of the Year Academy of Country Music Top Male Vocalist Academy of Country Music Video of the Year CMA Horizon Award |
