Awards
Country Music Association Award for Entertainer of the Year 2013, 1990, 1989
Academy of Country Music Award for Entertainer of the Year 2014, 1990
Kennedy Center Honors 2025
Country Music Association Award for Album of the Year 2008, 2007, 1997, ...
Troubadour, It Just Comes Natural, Carrying Your Love with Me, ...
Billboard Music Award for Top Country Artist 1996
Willie Nelson Lifetime Achievement Award 2024
Grammy Award for Best Contemporary Country Album 2009
Troubadour
Country Music Association Award for Single of the Year 2008, 1996
I Saw God Today, Check Yes or No
Academy of Country Music Award for Album of the Year 1998, 1997, 1986
Carrying Your Love with Me, Blue Clear Sky, Does Fort Worth Ever Cross Your Mind
Academy of Country Music Award for Dick Clark Artist of the Decade 2009
American Music Award for Favorite Country Album 1998, 1997
Carrying Your Love with Me, Blue Clear Sky
Country Music Association Award for Male Vocalist of the Year 1998, 1997, 1996, ...
CMT Music Award for CMT Performance of the Year 2022
Is Anybody Goin’ to San Antone (from CMT GIANTS: Charley Pride)
Country Music Association Award for Musical Event of the Year 2005
Good News, Bad News
Academy of Country Music Award for Male Artist of the Year 1998, 1997, 1989, ...
Academy of Country Music Award for Song of the Year 2007
Give it Away
Academy of Country Music Award for Single of the Year 2007, 1996
Give It Away, Check Yes or No
American Music Award for Favorite Male Artist Country 1998, 1991
Academy of Country Music Awards Cliffie Stone Icon Award 2017
Billboard Music Award for Top Country Tour 2020
Country Music Association Award for Vocal Event of the Year 2000
Murder on Music Row
Academy of Country Music Awards Gene Weed Special Achievement Award 2003
Academy of Country Music Milestone Award for ACM Winner Over Four Decades 2015
