[[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) [[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) ]]
Gaztaroan hasi zen kantak idazten, eta musika-talde bat sortu zuen arreba Bobbierekin. 1959an, kanta bat argitaratu zion diskoetxe batek. Horren ondoren, musikagile eta baxu-jotzaile gisa kontratatu zuen Ray Pricek, Honky-Tonk delako mugimenduko izarra zenak. Country musikaren barruan, Patsy Clineren ahotsean lehen postuetara iritsi zen Crazy kanta idatzi zuen. Roy Orbison eta Faron Youngen kanta arrakastatsu asko ere berak konposatu zituen.
1970ean, hainbat artistarekin hasi zen lanean, besteak beste, Waylon Jennings, Jessie Colter eta Kris Kristoffersonekin, eta outlaws delako mugimendua sortu zuten elkarrekin. Lan ospetsuenen artean ditu: Shotgun Willie (1973), The Troublemaker (1976), City of New Orleans (1984) eta The Promised Land (1986).