Awards
| Year | Association | Category | Result |
|---|---|---|---|
| 1990 | Billboard | Top New Male Artist | Won |
| Country Music Association | Horizon Award | Nominated | |
| 1991 | Won | ||
| 1992 | Vocal Event of the Year "This One's Gonna Hurt You" (with Marty Stuart) |
Won | |
| Grammy Awards | Best Country Collaboration with Vocals "The Whiskey Ain't Workin'" (with Marty Stuart) |
Won | |
| 1993 | Country Music Association | Vocal Event of the Year "I Don't Need Your Rockin' Chair" (with George Jones et al.) |
Won |
| 1996 | Vocal Event of the Year "Honky Tonkin's What I Do Best" (with Marty Stuart) |
Won | |
| 1999 | Grammy Awards | Best Country Collaboration with Vocals "Same Old Train" (with Marty Stuart et al.) |
Won |
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