80s Country Songs: 10 Greatest Hits, Ranked

The 80s gave us more than just big hair and huge shoulder pads. It was a phenomenal decade for country music. From the smooth pop-oriented style of the late Kenny Rogers to the legendary Randy Travis ushering in a new era of country music traditionalism, 80s country songs are some of the best of the genre and define a decade.

It was also a wonderful era for women in country music as Dolly Parton, The Judds and the late K.T. Oslin served up memorable hits such as “9 to 5”, “Grandpa (Tell Me ‘Bout the Good Old Days)” and “Hold Me,” respectively.

“The Red Headed Stranger” Willie Nelson dominated the charts and awards show during the decade. Willie’s hits demonstrated the diversity of his artistry as he was recognized for up tempo romps like “On the Road Again” and deeply poignant ballads like “You Were Always on My Mind.” Previously recorded by Elvis Presley, Willie put his signature spin on the song and took home a Grammy for Best Male Country Vocal Performance while the songwriters — Wayne Carson, Mark James and Johnny Christopher — earned the trophy for Best Country Song.

Here we take a look at the classic songs that dominated country radio airwaves in the 80s — each of which earned the Grammy Award for Best Country Song!

Top 80s country songs, ranked

Take a listen, feel transported back in time and see if you agree with our list — choosing the best was like choosing a favorite star in the sky.

10. “Hold Me” by K.T. Oslin (1989)

Country music is known for its storytelling and the late K.T. Oslin was one of the masters of the genre. Her gift really shines on this poignant song which chronicles an honest conversation between a married couple as the husband and wife each voice their challenges and in the end become closer for sharing. Released as the second single from Oslin’s This Woman album, it became her third No. 1 hit on the country chart and earned her the Best Country Song Grammy Award.

9. “You Decorated My Life” by Kenny Rogers (1980)

Released as the first single from Rogers’ album titled Kenny, this beautiful love song was written by Debbie Hupp and Bob Morrison. It became a No. hit on the country charts and peaked at No. 7 on Billboard’s all-genre Hot 100 chart. It won the Grammy for Best Country Song and was always a favorite in Kenny’s live shows.

8. “City of New Orleans” by Willie Nelson (1985)

This folksy anthem was written by legendary songwriter Steve Goodman, who won a posthumous Grammy for Best Country Song (in this category the trophy goes to the songwriter). Goodman died at 36 from leukemia but this song, describing a train ride from Chicago to New Orleans on the Illinois Central Railroad, has long been one of his most beloved compositions. Goodman originally recorded it and then it became a pop hit for Arlo Guthrie in 1972 before Willie took it to the top of the country chart in 1984.

7. “Highwayman” by The Highwaymen (1986) 80s country songs

Inspired by a particularly vivid dream, the song was written by legendary songwriter Jimmy Webb, and was recorded by the country music supergroup known as the Highwaymen —Willie Nelson, Waylon Jennings, Kris Kristofferson and Johnny Cash. The lyric is about a soul who is reincarnated and comes back as a highwayman (a thief who preyed on travelers in the old days), a sailor, a construction worker building a dam and lastly as the captain of a starship. The song went to No. 1 on the country chart and earned Webb a Grammy for writing the hit.

6. “Stranger in my House” by Ronnie Milsap (1984)

This piano-driven hit was written by former NFL standout Mike Reid, who played football for the Cincinnati Bengals before moving to Nashville and becoming a hit songwriter (he also co-wrote Bonnie Raitt’s “I Can’t Make You Love Me”) and also became a chart-topping artist in his own right.

But it was Ronnie Milsap who took this up-tempo tune to No. 5 on the country charts and made it one of his signature songs. It also became a crossover hit for Milsap, peaking at No. 23 on the pop chart and No. 8 on the adult contemporary chart. It beat out stiff competition from Deborah Allen’s “Baby I Lied,” Lee Greenwood’s “I.O.U.,” Alabama’s “Lady Down on Love” and Anne Murray’s “A Little Good News” to win the 1984 Grammy for Best Country Song.

5. “Grandpa (Tell Me ‘Bout the Good Ole Days)” by The Judds (1987)

Wynonna and Naomi Judd recorded this song on their Rockin’ with the Rhythm album. It became the mother/daughter duo’s sixth No. 1 hit on the Hot Country Singles chart and earned the Best Country Song Grammy for songwriter Jamie O’Hara. The Judds won the Grammy for Best Country Duo/Vocal Group Performance. (Click through to read about how Ashley and Wynonna Judd reunite after losing Naomi)

4. “On the Road Again” by Willie Nelson (1981) 80s country songs

Synonymous with the nomadic lifestyle of country singers, this song is an upbeat tribute to living life on a tour bus going from city to city to entertain fans. Willie wrote the song for the soundtrack of the 1980 film Honeysuckle Rose where he starred as a traveling musician juggling fame and family. Dyan Cannon starred as his wife and Amy Irving as the young musician that nearly wrecks his marriage. The song topped the country chart and won Willie the Grammy for Best Country Song. It was also nominated for an Oscar for Best Original Song during the 53rd Academy Awards. It has also been inducted into the Grammy Hall of Fame.

(You can also find Willie Nelson on our list of country songs about gratitude!)

3. “Forever and Ever Amen” by Randy Travis (1988)

Written by hit country songwriters Paul Overstreet and Don Schlitz, this well-crafted love song became Randy Travis third No. 1 single and remained at the top of the country chart for three weeks. In addition to winning Best Country Song at the 30^th annual Grammy Awards, “Forever and Ever Amen” also won Song of the Year honors from both the Country Music Association and the Academy of Country Music.

2. “9 to 5” by Dolly Parton (1982) 80s country songs

Dolly wrote this upbeat anthem about the rigors of working for a living for the film 9 to 5, in which she starred with Jane Fonda and Lily Tomlin. “9 to 5” topped three charts—country, adult contemporary and the all-genre Billboard Hot 100. It also earned an Academy Award nomination and won Dolly two Grammy Awards—Best Country Song and Best Country Vocal Performance, Female. (Click through to read the top 10 Dolly Parton movies, ranked)

1. “Always on My Mind” by Willie Nelson (1983)

Topping our list of 80s country songs is a ballad written by Wayne Carson, Mark James and Johnny Christopher, which has been recorded by several artists including Brenda Lee, John Wesley Ryles, Pet Shop Boys and Elvis Presley. But it’s Willie’s version that dominated the 25^th annual Grammy Awards. The song spent two weeks at No. 1 on the country chart and reached No. 5 on the Billboard Hot 100 for three weeks. It won three Grammy Awards — Best Male Country Vocal Performance, Best Country Song and the top honor, Song of the Year. The song also won multiple honors from the Country Music Association — Song of the Year in both 1982 and 1983, Single of the Year in 1982 and Willie’s album, Always on My Mind, won CMA Album of the Year in 1982.