100 Greatest Women, #92: Kelly Willis

100 Greatest Women: 10th Anniversary Edition


Kelly Willis

2008 Ranking: New Entry

While the 1990s were a golden era for women in country music, not every artist who emerged during that decade earned the commercial success that their talent and the quality of their music merited. For every Trisha Yearwood, Pam Tillis, and Deana Carter who broke through, there was a Mandy Barnett or a Julie Reeves who didn’t.

But there was no artist who, in retrospect, seems like more of a missed opportunity for Nashville than Kelly Willis.

Honing her craft as the frontwoman for a couple of bands who developed followings in the Austin, Texas, music scene, Willis impressed the likes of Lyle Lovett and Nanci Griffith, who brought her to the attention of Tony Brown at MCA Records. The label heavily promoted Willis’ debut record, Well-Travelled Love, which included the raucous single, “River of Love,” and a cover of John Hiatt’s “Drive South” that predicted Suzy Bogguss’ hit version of the song just a few years later. Despite glowing reviews, the album sold poorly, and none of its three singles charted.

It appeared that Willis’ star continued to rise, as she appeared in cameo roles in the films Thelma & Louise and Bob Roberts, as she prepared for her sophomore album. With compelling originals and some surprising choices of cover tunes, Bang Bang built upon the confident brand of rock-inflected country of her debut, but commercial success remained elusive.

With the release of her third album, a self-titled collection produced by Don Was, Willis finally seemed poised for a breakthrough. The set’s first two singles— “Whatever Way the Wind Blows” and a sultry reading of The Kendalls’ “Heaven’s Just a Sin Away”— finally put her name on the lower-rungs of the country airplay chart, and she scored a Best New Female Vocalist nomination from the Academy of Country Music. The popular press continued to recognize her; People magazine featured her in its “50 Most Beautiful” issue, while Rolling Stone named her the “Queen of Alternative Country” years before No Depression magazine started publication.

Willis, for her part, never seemed comfortable with the way MCA records attempted to market her, emphasizing her appearance over her powerhouse vocals and ear for quality material. She parted ways with the label after her third album, recording only sporadically over the next few years. She re-emerged, singing plaintive background vocals on “Angry All the Time,” a single by her second husband, acclaimed singer-songwriter Bruce Robison.

Robison penned several of the songs that ended up on Willis’ comeback album, 1999’s What I Deserve, which she recorded independently and then shopped around to several independent labels. The move to the indie route proved particularly fruitful for Willis: While she’d always been a critics’ favorite, What I Deserve earned the strongest reviews of her career, and it became her first album to chart on Billboard’s Top Country Albums chart, debuting at #30 on the strength of heavy CMT’s inclusion of her single, “Not Forgotten You,” in heavy rotation.

The album’s arrival during the peak of Shania Twain’s and Faith Hill’s most pop-leaning eras provided a counterpoint to the mainstream country that Willis had once courted. If that “Queen of Alternative Country” honorific seemed premature during her MCA tenure, it was a perfect fit for the second half of her career. Mining the same sonic territory as What I Deserve, Willis’ subsequent albums, Easy and Translated from Love, set the template for the nascent Americana movement with their thoughtful blend of traditional country, rockabilly, and contemporary folk. More than fifteen years into her career, Willis finally found a niche that appreciated her extraordinary talents.

In recent years, Willis has limited her touring and recording schedules to focus on raising her four children with Robison. The couple has released two terrific albums as a duo—2013’s Cheater’s Game and 2014’s Our Year— and Willis remains a fixture of the vibrant country scene in Austin.

Essential Singles

  • “River of Love,” 1990
  • “Baby, Take a Piece of My Heart,” 1991
  • “Whatever Way the Wind Blows,” 1993
  • “Not Forgotten You,” 1999
  • “Don’t Come the Cowboy with Me, Sonny Jim,” 2003
  • “Teddy Boys,” 2007
  • “9,999,999 Tears,” 2013

Essential Albums

  • Well-Travelled Love, 1990
  • Kelly Willis, 1993
  • What I Deserve, 1999
  • Easy, 2003
  • Translated from Love, 2007
  • Cheater’s Game (with Bruce Robison), 2013

100 Greatest Women: 10th Anniversary Edition

Next: #91. Lori McKenna

Previous: #93. Brandy Clark


  1. I felt bad for Kelly. Her voice and talent alone should of made her household name in the 90’s female mainstream country due to the diversity of pop-country, neo-traditional, and pure country that scattered throughout. It’s a shame, but Kelly has carved her own niche by putting out quality albums throughout the years.

  2. It was indeed a problem for Kelly, because it seems to me she would have easily fit in with the plethora of female artists that were so big during the 1990s. But it just might be that she was something of an outsider, from the Texas country scene, which has always been radically different from Nashville; and perhaps that was what kept her from being the big artist she should have been. I’m not saying that this is fair by any means, but it is what it is…unfortunately.

  3. One of the finest artists to emerge during the nineties, her albums have produced a very high quotient of excellent recordings. That she didn’t develop into a huge star is a damning indictment of the music business

  4. One of my favorite artists, dating from her very first album. I found her duets albums great additions to her work.

  5. Alas, I missed Kelly Willis when she arrived on the country scene in the early 90s. One of the benefits of this list though rectifies that – we can discover some great talent, thanks to countryuniverse.net, that does not get center stage. I’ve been listening to Kelly’s music this week, including some duets, with her husband. Her voice and music are stunning. If she is part of the Texas music scene, then she is confirming my judgment that some of our best music is coming out of there. And, maybe it is me, but is there a bit of Patty Loveless’s voice coming through Kelly? I am hearing it. If so, good thing that is!

  6. My dad loves Kelly Willis, but I don’t think I was familiar with her music at all until over a month ago, when I picked up a promotional cassette with three songs from her MCA debut (“Drive South”, “Red Sunset”, “Hole in My Heart”). Love her voice and her version of “Drive South” may be the only one that can hang with Suzy Bogguss’. Gives me high hopes for the quality of the Well-Travelled Love album, if I ever run across it. I think you owe me one for allowing for yet another discovery.

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