The 10 Best K.T. Oslin Songs of All Time

K.T. Oslin

Kay Toinette Oslin, better known by her stage name, K.T. Oslin, is a country music singer and songwriter. She began her career in 1966, although she did not release her first studio album until 1987. It was only after releasing her debut album that she achieved recognition and commercial success. The singer was at the height of her fame in the late 80s and early 90s. Sadly, K.T. Oslin died on December 21, 2020. She had had Parkinson’s disease for five years prior to her death, although it was not this condition that caused this demise. Oslin died a week after being diagnosed with COVID-19. During her career, K.T. Oslin has won three Grammy Awards. She is also inducted into the Nashville Songwriters Hall of Fame. The singer has released six studio albums, six compilation albums, one video album, seven music videos, and 25 singles. Here are the 10 best K.T. Oslin songs of all time.

10. Mary and Willie (1991)


The second single Oslin released from her third album, ‘Love in a Small Town,’ was ‘Mary and Willie.’ In the United States, it peaked at number 28, but it was more successful in Canada, where it reached number 20. K.T. Oslin was the sole writer of this track.

9. Didn’t Expect It to Go Down This Way (1989)


The final single Oslin released from the album ‘This Woman’ was ‘Didn’t Expect It to Go Down This Way.’ In the United States, it reached number 23 on the country chart, while it peaked at number 27 in Canada. K.T. Oslin wrote this song, which was produced by Harold Shedd. The B-Side to the song was #Round the Clock Lovin’.’

8. Money (1988)


The first single Oslin released from the album ‘This Woman’ was ‘Money,’ which reached number 13 on the country charts in the United States and number 11 in Canada. The message in this song was so strong that it influenced the film ‘Quiz Show’. Charles Van Doren was a quiz show contestant who was involved in a ‘fix’ scandal during the 1950s. The 1994 film, which starred Robert Redford, was based on the scandal, and Van Doren was invited to be a consultant on the film. However, he declined after listening to the message in the lyrics of ‘Money.’

7. 80’S Ladies (1987)


‘80’s Ladies’ is the title track from her 1987 debut album of the same name. It was K.T. Oslin’s first single to reach the top ten, as it peaked at number seven on the US Country chart. Country Thang Daily describes ‘80’s Ladies’ as the song that really kick-started K.T. Oslin’s career. For this song, Oslin won Grammy Awards for Best Female Country Vocal Performance and Song of the Year.

6. This Woman (1989)


‘This Woman’ is the title track and the fourth single released from the 1989 album of the same name. It reached number five in the United States and was more successful in Canada, where it peaked at number two. The single’s B-Side was ‘Younger Men.’ Like most of K.T. Oslin’s songs, it was produced by Harold Shedd.

5. Hey Bobby (1989)


‘Hey Bobby’ was a huge success in Canada, as it reached number one on the county charts. In the United States, the single peaked at number two. It was the third single from the album ‘This Woman.’ The B-Side to the single was ‘Where Is a Woman to Go.’

4. Hold Me (1988)


‘Hold Me’ was the second single released from the album ‘This Woman,’ and it was the second time that one of Oslin’s singles topped the country charts in Canada and the United States. The song differed from other country songs released at the time, as it has large sections of recitation. Oslin won Grammy Awards for Best Country Song and Best Country Vocal Performance by a Female. Although Oslin has never walked down the aisle, the theme of this song is marriage. She used the experiences of her friends to write the lyrics as though they were from a personal perspective.

3. Do Ya (1987)


K.T. Oslin’s first country chart-topping single was ‘Do Ya,’ which featured on her debut album, ‘80’s Ladies.’ While it topped the US Hot Country Songs chart, it reached number three on the Canadian country charts. By the time this song was released, K.T. Oslin was 45 years old, which is significantly older than most solo artists are when they achieve their first chart-topping hit.

2. Come Next Monday (1990)


‘Come Next Monday’ was Oslin’s third single to top the country charts in both the United States and Canada. It was the second single released from Oslin’s third album, ‘Love in a Small Town.’ K.T. Oslin co-wrote the song with Charlie Black and Rory Bourke. However, it was written for Judy Rodman, who released the original version in 1986. Oslin released her version of the song four years later.

1. I’ll Always Come Back (1987)


Oslin’s most commercially successful song was ‘I’ll Always Come Back.’ It was her second single to top the US Country charts and her first to top the country chart in Canada. The song featured on Oslin’s debut album. The song won Oslin Academy of Country Music Awards for Single Record of the Year and Video of the Year. It had been a long road for the talented singer and songwriter to get to this point, as she had begun her career in the music industry 21 years earlier.

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