Best Duets in Country Music History

By: Brian Zwerner

Sep 11, 2025

Some of country music’s most unforgettable moments have come when two legends joined forces. These collaborations not only topped the charts but also created timeless memories for fans.

At number three is Willie Nelson and Waylon Jennings with “Mamas Don’t Let Your Babies Grow Up to Be Cowboys.” The song was first recorded by Ed Bruce in 1975, but it became a cultural anthem when Nelson and Jennings included it on their 1978 album Waylon & Willie. Their version hit number one, earned a Grammy, and cemented the duo as outlaw icons.

Coming in at number two is “Jackson,” the fiery duet between Johnny Cash and June Carter. The track had been recorded before, but when Cash and Carter released their version in 1967, it was unforgettable. The chemistry between the couple was undeniable, and the song became a number two hit while also winning them a Grammy. Fans still consider it one of the greatest showcases of their partnership both on and off stage.

The top spot goes to Kenny Rogers and Dolly Parton with “Islands in the Stream.” Written by the Bee Gees, this crossover hit dominated the charts, reaching number one in country, pop, and adult contemporary. More than just a song, it became a defining moment in both artists’ careers and a staple of American music history.

Country music duets may come and go, but these three remain untouchable.

© Country Bios 2025

© Country Bios 2025

© Country Bios 2025