| Year | Award | Category |
|---|---|---|
| 2007 | CMT Music Awards | Album of the Year - Water & Bridges |
| 2005 | CMT Music Awards | Favorite All Time Country Duet - "Islands In the Stream" (w/ Dolly Parton) |
| 2004 | CMT's 100 Greatest Cheating Songs | "Ruby Don't Take Your Love to Town"- #6 |
| 2003 | International Entertainment Buyers Association | Lifetime Achievement Award |
| 2003 | CMT's 100 Greatest Country Songs | "The Gambler" - #26 |
| 2002 | CMT's 40 Greatest Men of Country Music | Ranking - #19 |
| 2000 | TNN Music Awards | Career Achievement Award |
| 1999 | BBC's Greatest Country Singer | Ranking - #2 |
| 1988 | Grammy Awards | Best Duo Country Vocal Performance - "Make No Mistake She's Mine" (w/ Ronnie Milsap) |
| 1986 | USA Today | Favorite Singer of All Time |
| 1985 | American Music Awards | Favorite Country Album - Eyes That See In the Dark |
| 1985 | American Music Awards | Favorite Male Country Artist |
| 1983 | Academy of Country Music Awards | Single of the Year - "Islands In the Stream" (w/ Dolly Parton) |
| 1983 | Academy of Country Music Awards | Top Vocal Duet - (w/ Dolly Parton) |
| 1983 | American Music Awards | Favorite Pop/Rock Country Artist |
| 1983 | American Music Awards | Favorite Country Single - "Love Will Turn You Around" |
| 1983 | ASAP Awards | Favorite Single - "Islands In the Stream" (w/ Dolly Parton) |
| 1982 | American Music Awards | Favorite Country Album - Greatest Hits |
| 1981 | American Music Awards | Favorite Pop/Rock Male Artist |
| 1981 | American Music Awards | Favorite Country Album - The Gambler |
| 1981 | American Music Awards | Favorite Country Single - "Coward of the County" |
| 1980 | American Music Awards | Favorite Male Country Artist |
| 1980 | American Music Awards | Favorite Country Album - The Gambler |
| 1980 | Music City News Country | Single of the Year |
| 1979 | American Music Awards | Favorite Male Country Artist |
| 1979 | American Music Awards | Favorite Country Album - 10 Years of Gold |
| 1979 | Country Music Association Awards | Male Vocalist of the Year |
| 1979 | Country Music Association Awards | Vocal Duo of the Year - (w/ Dottie West) |
| 1979 | Country Music Association Awards | Album of the Year - The Gambler |
| 1979 | Music City News Country | Male Artist of the Year |
| 1979 | Music City News Country | Single of the Year - "The Gambler" |
| 1979 | Grammy Awards | Best Male Country Vocal Performance - "The Gambler" |
| 1978 | American Music Awards | Favorite Single - "Lucille" |
| 1978 | Country Music Association Awards | Vocal Duo of the Year - (w/ Dottie West) |
| 1978 | Academy of Country Music Awards | Entertainer of the Year |
| 1978 | Academy of Country Music Awards | Top Male Vocalist |
| 1977 | Country Music Association Awards | Single of the Year - "Lucille" |
| 1977 | Academy of Country Music Awards | Top Male Vocalist |
| 1977 | Academy of Country Music Awards | Single of the Year - "Lucille" |
| 1977 | Academy of Country Music Awards | Song of the Year - "Lucille" |
| 1977 | Grammy Awards | Best Male Country Vocal Performance - "Lucille" |
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