Her 1987 debut album of the same name would sell over one million copies and produce three additional hits, including the number one single "Do Ya".

Oslin released This Woman (1988) and Love in a Small Town (1990), which reached the top ten of the Billboard charts.

Oslin's mother had once performed Swing music on local radio and also was offered a job singing in the Les Brown orchestra.

[3] She studied drama at Lon Morris College in Texas, where she also drew a deep appreciation for folk music.

[2][4] While in college, Oslin formed a folk trio with David Jones and singer-songwriter Guy Clark.

[10] Oslin eventually made a demonstration tape of her compositions and brought them to the attention of the performance rights group SESAC.

[10] Only two singles were issued on the label, "Younger Men" and "Clean Your Own Tables", the latter of which became a minor hit on the country chart.

Yet Petty continued advocating for Oslin and her original compositions were recorded by Judy Rodman, Dottie West, Gail Davies and The Judds.

She borrowed seven thousand dollars from her aunt, lost 40 pounds, rented a Nashville nightclub and invited record executives to a one-time music showcase.

Yet, through her connections, Oslin contacted Nashville producer Harold Shedd, who had recently been successful recording Alabama.

Alex Henderson of Allmusic gave it a three-star rating, calling it "a generally appealing release that successfully balances commercial and artistic considerations.

That year, she performed at Carnegie Hall alongside new singer Clint Black,[28] who also served as the opening act of her newly established headlining tour.

However, he found the quality of the writing and sound to be quite high: "This is great pop music, no matter what bin you find it in.

Directed by Peter Bogdanovich, the film's plot focused on Nashville and the main character's dream of becoming a country music songwriter.

Bill Carpenter commented that "The only issue is that this was marketed as a country album when the Nashville element isn't terribly conspicuous.

"[45] Alanna Nash found the album to be "schizophrenic" in its musical diversity, but did praise Oslin's vocal performance throughout.

[47] Its title track was released as the first single and reached a minor chart position on the country songs list.

[13] Its second single, a cover of Rosemary Clooney's "Come on-a My House" would make the Billboard dance music chart.

Examples of pop and "anthemic rock" can be found in her first two RCA albums, as noted by Steve Huey of Allmusic.

[5] When reviewing 1988's This Woman, Allmusic's Alex Henderson also drew similar comparisons, calling her sound "far from a honky tonker.

"[25] Oslin incorporated more dance, traditional pop, Latin and Americana into her musical style after leaving RCA.

[51] Bill Friskics-Warren of The New York Times wrote that Oslin "gave voice to the desires and trials of female baby boomers on the cusp of middle age.

"[2] In Finding Her Voice: The History of Women in Country Music, Oslin "became the beacon of inspiration for every middle-aged woman who felt vibrant yet overlooked.

"[53] Dennis Hunt of The Los Angeles Times called her writing "penetrating, vivid tales of women in turmoil.

"[51] Oslin was largely influenced as a child by traditional pop and country performers, notably Patsy Cline and Kay Starr.

[51] Oslin's success helped give identity to strong, female women in their middle-aged years, according to several publications.

[56] Mary Bufwack and Robert K. Oermann commented on her musical legacy in 2003: "K. T. was part of a 1980s invasion of female songwriting talent into Nashville.

Writers and critics have cited her as an innovator of Nashville's musical shift, along with Steve Earle, k. d. lang and Lyle Lovett.

[51] Bill Friskics-Warren of The New York Times commented that Oslin was "among a distinguished circle of thoughtful, independent female songwriting contemporaries that included Pam Tillis, Gretchen Peters and Matraca Berg.

[63][40] She was interred at Woodlawn Memorial Park in Nashville adjacent to fellow country music star Tammy Wynette.