Before the new set of lucky winners will be presented on Feb. 10, let’s recall some of the classic records that have been awarded Best Country Song by the program since it first aired in 1959. To clarify, we define ‘classic songs’ here as those that have been awarded up to the year 1999. Winners in 2000 and the years onward were not covered in our story.
The Best Country Song Award is presented to the writer(s) or composer(s) of a single song. Hence, it is also known as Country Songwriter’s Award. While the prestigious awarding program started in 1959, it was only in 1965 when they began awarding this category. The years reflect the period when Grammy presented the award for the music released in the previous year.
Here are the 35 classic hits that won Grammy’s Best Country Song title.
#1. Dang Me (1965)
We know this song to have been made popular by Roger Miller. As he is also the songwriter of the hit, the award went to him. That makes him the first county artist to win Grammy’s Best Country Song award. “Dang Me” was Miller’s first top country single and first Top 10 crossover hit.
#2. King of the Road (1966)
The following year, Miller garnered his second consecutive win for the award for the song “King of the Road.” Penned by himself, the song reached No. 1 not only in the U.S. but also in other countries, including the U.K. and Norway. It became one of the best-known records of his career.
#3. Almost Persuaded (1967)
Songwriters Glenn Sutton and Billy Sherrill collaborated for the writing of this song. Hence they received the Song of the Year award for it. David Houston first recorded it in 1966. In August that year, the song reached No. 1 on the country chart and stayed there for nine weeks.
#4. Gentle on My Mind (1968)
The Best County Song Accolade was given to John Hartford at the 10th Annual Grammy Award for his composition “Gentle on My Mind.” The song also won three more awards from Grammy’s that same year. Many notable artists covered his song such as Glen Campbell, Dean Martin, Elvis Presley, among others. Glen Campbell’s version was considered the most successful of all. It garnered one of the three other Grammy awards bestowed to this song namely, Best Country & Western Recording.
#5. Little Green Apples (1969)
This song was a composition of Bobby Russell and originally recorded by Roger Miller. His version became a Top 40 pop hit. In addition to the Best Country Song title, “Little Green Apples” also won the Song of the Year award. Aside from Miller, Patty Smith, and O.C. Smith were among the other artists who covered the song.
#6. A Boy Named Sue (1970)
Humorist and poet Shel Silverstein wrote this song and Johnny Cash propelled it to fame. He sang it at his concert at California’s San Quentin State Prison in February 1969. The live version appeared on his album, At San Quentin, and became his biggest hit on the pop chart. It also topped both the Hot Country Songs and Hot Adult Contemporary Tracks charts.
#7. My Woman, My Wife (1971)
Marty Robbins was awarded the Best Country Song title at the 13th Annual Grammy Award for this song. He wrote and recorded the song. He released it as the first single and title track of his album of the same name in January 1970. Subsequently, the song topped the country chart, earning him his 14th No. 1 single.
#8. Help Me Make It Through the Night (1972)
This country ballad was a composition of Kris Kristofferson. He also recorded a version which he included on his 1970 eponymous album. Later that same year, Sammi Smith covered the song and released it on her album Help Me Make It Through the Night. It became No. 1 on the country chart and No. 8 on the pop chart. Her recording remains the best-selling and most famous version in the U.S. It went on to become her signature song. Many renowned artists also recorded the song including Loretta Lynn, Elvis Presley, and Willie Nelson.
#9. Kiss an Angel Good Morning (1973)
Charley Pride earned his eighth top country hit as well as his first major crossover single with this song. It also entered other music charts and became one of Pride’s signature songs. While many would often associate the song with Pride, let’s also not forget the man who wrote it. He is no other than Ben Peters and he received the Best Country Song award for this hit at the 15th Annual Grammy Awards.
#10. Behind Closed Doors (1974)
Charlie Rich was the first to record this song which was written by Kenny O’Dell. Rich earned his first No. 1 country record and won several awards for the song. Aside from garnering the Best Country Song accolade at the 16th Annual Grammy Award, its artist also bagged the Best Male Country Vocal Performance trophy. The Country Music Television ranked the song No. 1 in its 100 Greatest Songs in Country Music in 2003.
#11. A Very Special Love (1975)
This song was made famous by Charlie Rich. Billy Sherrill and Norro Wilson penned the lyrics and they won a Best Country Song award for it from the Grammy’s. “A Very Special Love” reached No. 1 on both the country music chart and adult contemporary chart. The song was a follow-up to Rich’s “The Most Beautiful Girl in the World.”
#12. (Hey Won’t You Play) Another Somebody Done Somebody Wrong Song (1976)
Larry Butler and Chips Moman wrote this pop country song and earned them a Grammy Award for Best Country Song. B.J. Thomas made it famous in 1975. Thomas scored his second No. 1 single with this lengthy-titled hit. The song also had a significant impact on the singer’s career, propelling his future success as a mainstream country artist. Kenny Rogers and Dottie West recorded a duet version in 1981.
#13 Broken Lady (1977)
Larry Gatlin wrote and recorded this song. It was released as the first single from his 1975 album High Time. The song entered the country chart’s Top 5, giving Gatlin his second big hit. It also won him Grammy’s Best Country Song award in 1977. Dottie West also covered this song.
#14. Don’t It Make My Brown Eyes Blue (1978)
This Crystal Gayle record was penned by Richard Leigh. It’s one of the three songs he wrote that became part of the Top 10 hits for the singer. Released in March 1977, the song was the first single on her album We Must Believe in Magic. The song reached worldwide popularity, appearing in several music charts in different countries. Apart from giving Leigh a Best Country Song award, it also won Gayle the Best Female Country Vocal Performance title.
#15. The Gambler (1979)
This song is one of Kenny Rogers’ well-known hits. Don Schlitz wrote it in 1976 at the age of 23. While Roger made it famous, several singers attempted to record it ahead of him. It was Bobby Bare who first recorded the song. Schlitz recorded a version as well but was only a minor hit on the country chart. In 1978, Johnny Cash included his cover on his Gone Girl album. Later that year, the song finally reached a breakthrough with Rogers taking it atop the country chart. He also won the Best Male Country Vocal Performance from Grammy’s in 1980.
#16. You Decorated My Life (1980)
Debbie Hupp and Bob Morrison teamed up for the writing of this song. Kenny Rogers recorded it and became Kenny album’s lead single. It reached the top of the country chart while peaking at No. 7 on the pop chart.
#17. On the Road Again (1981)
The country music outlaw singer Willie Nelson wrote and recorded this song. As its title suggests, the song narrates life on tour. With it, he scored his 9th top country song as a solo performer. He began writing the song after the executive producer of the film Honeysuckle Rose approached him. The song then became the soundtrack to the movie which Nelson also starred in.
#18. 9 to 5 (1982)
This song was the flagship of Dolly Parton’s 9 to 5 and Odd Jobs album. She wrote and originally recorded the song. It was created as a soundtrack to the 1980 comedy film with the same. Parton won two Grammy Awards for the song namely, Best Country Song and Best Country Female Vocal Performance.
#19. Always on My Mind (1983)
Written by Johnny Christopher, Mark James, and Wayne Carson, this song appealed to several artists. B.J. Thomas, Brenda Lee, and Elvis Presley were among those who recorded it. However, Willie Nelson’s version became the most remarkable. It did not only top the country music chart, but also won three trophies at the 25th Grammy Awards. Its songwriters brought home the Song of the Year and Best Country Song awards while Nelson bagged the Best Male Country Vocal Performance accolade.
#20. Stranger in My House (1984)
Country music artist and composer Mie Reid wrote this song which would give Ronnie Milsap a Top 10 hit on the country and adult contemporary charts. In Canada, the song was more popular at it reached the highest spot of the Canadian RPM Country Tracks chart. The song dropped in 1983 and appeared as the first single on Milsap’s Keyed Up album.
#21. City of New Orleans (1985)
Willie Nelson was back on our list for recording singles that won Grammy’s Best Country Song award. His version of “City of New Orleans” earned its writer, Steve Goodman,the said title in 1985 posthumously. Moreover, Nelson’s cover was a top country hit both in the U.S. and Canada.
#22. Highwayman (1986)
Jimmy Webb wrote this song and he recorded it first in 1977. After him, several other singers recorded the song, including Glen Campbell and The Highwaymen. The latter comprising of Johnny Cash, Willie Nelson, Kris Kristofferson, and Waylon Jennings took the song to the top of the country chart which run for twenty weeks. Thanks to their cover, Webb won Grammy’s Best Country Song award in 1986. Meanwhile, their album where the song appeared became a No. 1 platinum-selling album.
#23. Grandpa (Tell Me ‘Bout the Good Ol’ Days) (1987)
This song was written by Jamie O’Hara. The music duo The Judds recorded it in 1986 and earned them their sixth No. 1 on the country chart. The song became a well-known hit in the U.S. and Canada. The second single on their Rockin’ with the Rhythm album. Moreover, the song was chosen as one of the Top 100 Western songs of all time.
#24. Forever and Ever, Amen (1988)
Randy Travis earned his third country hit with this song which Paul Overstreet and Don Schlitz wrote. It was the first single on his Always & Forever album released in March 1987. “Forever and Ever, Amen” topped the country charts in the U.S. and Canada. The song was also Travis’ first single as a solo artist to receive a gold certification from RIAA.
#25. Hold Me (1989)
This song was penned and recorded by K.T. Oslin. It was the second single on her album This Woman. Released in September 1988, “Hold Me” gave the singer her third No. 1 country single. It was a chart-topper both in the U.S. and Canada.
#26. After All This Time (1990)
Rodney Crowell wrote and recorded this song which earned him a Grammy Award in 1990. Crowell scored his seventh No. 1 with the song which was released in January 1989. It was the fourth single from his Diamonds & Dirt album.
#27. Where’ve You Been (1991)
Kathy Mattea recorded this song written by Don Henry and John Vezner. The songwriters won the Best Country Song award from Grammy for the song. While the single failed to reach the top of the chart, it gave Mattea a Top 10 hit. Moreover, it won her the Best Country Performance, Female title from Grammy. “Where’ve You Been” is a song about two lovers, Edwin and Clair. It was released in November 1989 and appeared as the third single from Mattea’s album Willow in the Wind.
#28. Love Can Build a Bridge (1992)
This is the second record of The Judds that won Grammy’s Best Country Song award. “Love Can Build a Bridge” was under the authorship of John Barlow Jarvis, Paul Overstreet, and one half of the duo, Naomi Judd. This was the second single from their album of the same name and became a Top 5 country hit.
#29. I Still Believe in You (1993)
Vince Gill co-wrote this song with John Barlow Jarvis. It won the Best Country Song award at the 35th Annual Grammy Awards. This gives the song’s co-writer Jarvis his second consecutive win for the said title from the same awarding body. It also gave Gill the first of his five No. 1 country singles.
#30. Passionate Kisses (1994)
This Lucinda Williams’ composition was a Grammy Award winner, thanks to Mary Chapin Carpenter who recorded it. While Williams also recorded the song, it was Carpenter’s version that made her win the said title. On the other hand, the song earned Carpenter another Top 5 country hit and won her the Best Female Country Vocal Performance trophy from Grammy.
#31. I Swear (1995)
Gary Baker and J. Myers penned this song which became a big hit for John Michael Montgomery in 1994. His record reached the country chart’s summit and its reign atop lasted for four weeks. It was also a minor crossover hit peaking at No. 42 on Billboard Hot 100. Two months after, the song dominated the country chart’s highest spot, the R&B group All-4-One covered it and their version reached worldwide success.
#32. Go Rest High on that Mountain (1996)
Vince Gill earned his second Best Country Song award for this eulogy ballad. After the death of country music icon Keith Whitley in 1989, Gill was inspired to write this song. However, the singer was able to complete the song only after his brother’s death in 1993. He also recorded a version of his self-penned tune which was released in 1995. In 2013, Gill performed the song at the funeral of George Jones.
#33. Blue (1997)
This song was written by Bill Mack. He first recorded it in 1956 and was released as a single two years later. Since then, many artists had covered the song. The most notable version of it was probably that of LeAnn Rimes. It won Mack the Best Country Song at the 1996 Grammy Awards. Additionally, Rimes garnered the Best Female Country Vocal Performance accolade for her rendition of the song.
#34. Butterfly Kisses (1998)
Bob Carlisle co-wrote this song with Randy Thomas and it made him win a Best Country Song award from Grammy. Carlisle penned the tune for her daughter Brooke on the occasion of her 16th birthday. His record was released in 1997 on his Butterfly Kisses (Shades of Grace) album. The song reached No. 1 on the adult contemporary charts both in the U.S. and Canada.
#35. You’re Still the One (1999)
This single of the Canadian singer Shania Twain was the first to be released to pop and international markets. The song never reached No. 1 on any music chart but it was Twain’s most successful pop hit. The song was also one of the singer’s most successful country records. In fact, it won her two Grammy awards in 1999. These were the Best Country Song and Best Female Country Vocal Performance accolades.