[[Grammy Award for Best Male Country Vocal Performance(en) ]] (1975) [[Country Music Association Award for Entertainer of the Year(en) ]] (1976) [[Favorite Country Single(en) ]] (1977) : [[Blue Eyes Crying in the Rain(en) ]] [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1978) [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1978) [[Country Music Association Award for Entertainer of the Year(en) ]] (1979) [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1979) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1979) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1980) [[Grammy Award for Best Country Song(en) ]] (1980) : [[On the Road Again(en) ]] [[Favorite Country Male Artist(en) ]] (1980) [[Country Music Association Award for Entertainer of the Year(en) ]] (1980) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1981) : [[Somewhere Over the Rainbow(en) ]] [[Favorite Country Male Artist(en) ]] (1981) [[Country Music Association Award for Entertainer of the Year(en) ]] (1982) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1982) [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1982) [[Grammy Award for Record of the Year(en) ]] (1982) [[Favorite Country Male Artist(en) ]] (1982) [[Favorite Country Single(en) ]] (1982) : [[On the Road Again(en) ]] [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1983) : [[Take It to the Limit(en) ]] [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1983) : [[Pancho & Lefty(en) ]] [[People's Choice Award for Favorite Country Artist(en) ]] (1983) [[American Music Award for Favorite Pop/Rock Album(en) ]] (1983) : [[Always on My Mind(en) ]] [[Country Music Association Award for Entertainer of the Year(en) ]] (1983) [[American Music Award for Favorite Country Album(en) ]] (1983) : [[Always on My Mind(en) ]] [[Favorite Country Male Artist(en) ]] (1984) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1984) [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1984) [[People's Choice Award for Favorite Country Artist(en) ]] (1984) [[Grammy Award for Best Country Performance by a Duo or Group with Vocal(en) ]] (1985) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1985) [[Country Music Association Award for Entertainer of the Year(en) ]] (1986) [[Favorite Country Single(en) ]] (1986) : [[Forgiving You Was Easy(en) ]] [[American Music Award for Favorite Country Album(en) ]] (1986) : [[City of New Orleans(en) ]] [[Favorite Country Male Artist(en) ]] (1986) [[Favorite Country Male Artist(en) ]] (1987) [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (1990) : [[Highwayman 2(en) ]] [[People's Choice Award for Favorite Country Artist(en) ]] (1990) [[Grammy Award for Best Traditional Pop Vocal Album(en) ]] (1994) : [[Moonlight Becomes You(en) ]] [[Grammy Award for Best Male Country Vocal Performance(en) ]] (1997) [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (1999) [[Grammy Award for Best Pop Instrumental Performance(en) ]] (1999) : [[Night and Day(en) ]] [[Grammy Award for Best Music Film(en) ]] (2000) [[Grammy Award for Best Country Album(en) ]] (2001) : [[Rainbow Connection(en) ]] [[Grammy Award for Best Male Country Vocal Performance(en) ]] (2001) [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (2002) [[Grammy Award for Best Country Album(en) ]] (2002) : [[The Great Divide(en) ]] [[Grammy Award for Best Country Album(en) ]] (2003) : [[Live and Kickin'(en) ]] [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (2003) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (2004) [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (2004) [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (2005) [[Grammy Award for Best Male Country Vocal Performance(en) ]] (2005) [[Grammy Award for Best Country Album(en) ]] (2006) : [[You Don't Know Me: The Songs of Cindy Walker(en) ]] [[Grammy Award for Best Country Collaboration with Vocals(en) ]] (2007) [[Grammy Award for Best Traditional Pop Vocal Album(en) ]] (2009) : [[American Classic(en) ]] [[Grammy Award for Best Americana Album(en) ]] (2009) : [[Willie and the Wheel(en) ]] [[Grammy Award for Best Pop Collaboration with Vocals(en) ]] (2009) [[Grammy Award for Best Americana Album(en) ]] (2010) : [[Country Music(en) ]]