The 5 Most Meant-to-Be Country Duets and Collaborations

When great minds come together, they produce great things, or so the saying goes. It holds true for these great country collaborations, which brought together some of the greatest musicians of their time. From romantic duets to genre-bending viral hits, these country collaborations have gone down in history. 

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1. “Jackson” — Johnny Cash and June Carter

Choosing the best collaboration between country greats (and real-life married couple) Johnny Cash and June Carter is hard. They sang many duets together both before and after they got married. One of the most iconic is “Jackson,” an upbeat, playful song about a couple going on a road trip hoping to fix their marriage. Cash and Carter shine in their performance because of their musical talents and their knack for humor, which comes out in their playful rendition. The couple had other great duets, such as “It Ain’t Me Babe” and “Long-Legged Guitar-Pickin’ Man,” but “Jackson” ranks toward the very top. 

2. “Islands in the Stream” — Dolly Parton and Kenny Rogers

One of the most famous country duets ever, “Islands in the Stream” wasn’t originally written as a country song. In fact, it wasn’t even written by either of the great singers who popularized it. Written by the Bee Gees, “Islands in the Stream” was supposed to be an R&B song, ideally performed by Diana Ross or Marvin Gaye. There is still some argument about whether Parton’s and Rogers’ version is technically country. Many times it seems to be classified as simply soft rock. Still, it topped the country charts after its release, and is regularly named on lists of the top country duets ever. With two country giants like Parton and Rogers at its helm, it’s safe to say that “Islands in the Stream” belongs on pretty much every list. 

3. “Mammas, Don’t Let Your Babies Grow Up to Be Cowboys” — Willie Nelson and Waylon Jennings

In the 1970s, Willie Nelson was stepping out into the new genre of outlaw country, characterized by disdain for the law and authority. In 1978, he teamed up with Waylon Jennings to record the album Waylon & Willie, an exploration of the genre. One of the album’s standouts was their cover of “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” first recorded by Ed Bruce. Nelson’s and Jennings’ version perfectly encapsulates the sorrow of the outlaw, with both men providing a yearning vocal performance that earned the song a place in country music history. The cover earned a Grammy Award, too, on the way to the rendition becoming the best-known version of the track. 

4. “Louisiana Woman, Mississippi Man” — Loretta Lynn and Conway Twitty

Loretta Lynn and Conway Twitty were both massively successful artists on the country scene of the 1960s and 1970s. They collaborated on 11 albums between 1971 and 1988. One of the most revered is Louisiana Woman, Mississippi Man. The album’s title track was their third hit to reach No. 1 on the country charts, and it became one of their signature songs as a duo. Its popularity was driven by their distinctive vocal harmonies and the song’s colorful Cajun feel, making it a favorite classic country duet. 

[RELATED: We Asked AI to Write a Modern Duet Between Loretta Lynn and Conway Twitty]

5. “Old Town Road” — Lil Nas X and Billy Ray Cyrus

Don’t roll your eyes at this one, because it is iconic! The 2019 remix of “Old Town Road” features Billy Ray Cyrus collaborating with then-new hip-hop artist Lil Nas X. The collab has been widely credited with making country-rap an even more widespread sensation. It also included a tongue-in-cheek depiction of modern country stars,who might not be very “country” at all: My life is a movie / Bull riding and boobies / Cowboy hat from Gucci / Wrangler on my booty. “Old Town Road” sparked a viral challenge and made Lil Nas X a star after the unlikely collaboration with one of the biggest country stars of the 1990s.

Photo by Michael Ochs Archives/Getty Images

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