| Year | Awards | Award | Outcome |
|---|---|---|---|
| 1995 | Academy of Country Music | Top New Female Vocalist | Won |
| 1996 | TNN/Music City News Awards | Star of Tomorrow | Nominated |
| Jukebox Awards | Best New Artist | Nominated | |
| 1999 | Academy of Country Music | Top Female Vocalist | Nominated |
| Best Music Video — "Single White Female" | Nominated | ||
| Country Music Television | Female Video of the Year — "Single White Female" | Nominated | |
| Country Weekly Awards | Fast Track Artist | Nominated | |
| Country Music Association Awards | Horizon Award | Nominated | |
| 2000 | Horizon Award | Nominated | |
| 2001 | Country Weekly Awards | Vocal Collaboration — "Hard to Be a Husband, Hard to Be a Wife" | Nominated |
| MENC | Stand Up for Music Award | Won | |
| Country Music Association Awards | Vocal Event of the Year — "Hard to Be a Husband, Hard to Be a Wife" | Nominated | |
| 2002 | CMT Flameworthy Awards | Video Fashion Plate — "Jezebel" | Won |
| People Magazine | 50 Most Beautiful People | Won | |
| International Bluegrass Music Association | Recorded Event of the Year — Clinch Mountain Sweethearts | Won | |
| MENC | FAME Award | Won | |
| 2005 | Country Weekly Awards | Star with Biggest Heart | Nominated |
| Best Patriotic Song — "The Bumper of My SUV" | Nominated | ||
| 2006 | Star with Biggest Heart | Nominated | |
| 2010 | Black Tie Dinner | Media Award | Won |
| OUTmusic Awards | Vanguard Award | Won | |
| 2011 | Kansas Music Hall of Fame | Inducted | Won |
| GLAAD Media Awards | Outstanding Musical Artist | Nominated | |
| Lambda Literary Awards | Best Biography-Like Me | Nominated | |
| Documentary Channel Audience Award-Nashville Film Festival | Best Documentary-Wish Me Away | Won | |
| Los Angeles Film Festival | Best Documentary-Wish Me Away | Won |
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