The 20 best duets in country music history

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The 20 best duets in country music history

Amy McCarthy

Posted: July 15, 2023 | Last updated: April 13, 2024

<p>Bringing together the genre's finest talents has always been a country music staple. From the legendary duets between Conway Twitty and Loretta Lynn to more modern collaborations between husband-and-wife duo Faith Hill and Tim McGraw, there's no denying that country music produces a ton of really great duets. </p><p>Looking for the finest? Flip through the gallery below for a look at 20 of the finest duets in country music history. </p>

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The 20 best duets in country music history

Bringing together the genre's finest talents has always been a country music staple. From the legendary duets between Conway Twitty and Loretta Lynn to more modern collaborations between husband-and-wife duo Faith Hill and Tim McGraw, there's no denying that country music produces a ton of really great duets.

Looking for the finest? Flip through the gallery below for a look at 20 of the finest duets in country music history.

<p>Bringing together three '90s country powerhouses, "If You See Her/If You See Him," is a quintessential break-up song. Released in 1998, the song was an instant hit, reaching #1 on what is now the Billboard Hot Country Songs chart. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/the_best_fictional_films_from_real_films/s1__33080750'>The best fictional films from real films</a></p>

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"If You See Him/If You See Her," Reba McEntire with Brooks & Dunn

Bringing together three '90s country powerhouses, "If You See Her/If You See Him," is a quintessential break-up song. Released in 1998, the song was an instant hit, reaching #1 on what is now the Billboard Hot Country Songs chart.

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<p>A #2 hit for Johnny Cash and June Carter in 1967, "Jackson" has been recorded by multiple artists, including Nancy Sinatra and Lee Hazlewood, INXS, and the Carolina Chocolate Drops. But it's definitely most associated with country music's most legendary couple, who won a Grammy Award for their recording of Jackson the following year for Best Country Western Performance by a Duet, Trio, or Group. </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

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"Jackson," Johnny Cash and June Carter Cash

A #2 hit for Johnny Cash and June Carter in 1967, "Jackson" has been recorded by multiple artists, including Nancy Sinatra and Lee Hazlewood, INXS, and the Carolina Chocolate Drops. But it's definitely most associated with country music's most legendary couple, who won a Grammy Award for their recording of Jackson the following year for Best Country Western Performance by a Duet, Trio, or Group.

<p>Arguably the most iconic country music duet, this collaboration between Dolly Parton and Kenny Rogers was a massive crossover hit in 1983. The song was #1 on the all-genre Billboard Hot 100 and was originally intended for soul singer Marvin Gaye before it was reworked to be a country classic. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/steven_spielbergs_20_best_movies_ranked/s1__38134707'>Steven Spielberg's 20 best movies, ranked</a></p>

Beth Gwinn/Redferns

"Islands In The Stream," Dolly Parton and Kenny Rogers

Arguably the most iconic country music duet, this collaboration between Dolly Parton and Kenny Rogers was a massive crossover hit in 1983. The song was #1 on the all-genre Billboard Hot 100 and was originally intended for soul singer Marvin Gaye before it was reworked to be a country classic.

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<p>This tragic tune was a sleeper hit for Brad Paisley and Alison Krauss in 2004. Despite its morose subject matter -- "Whiskey Lullaby" runs the gamut from alcoholism to love and loss -- the song was a commercial and critical hit, winning Song of the Year at the 2005 CMA Awards. </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

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"Whiskey Lullaby," Brad Paisley and Alison Krauss

This tragic tune was a sleeper hit for Brad Paisley and Alison Krauss in 2004. Despite its morose subject matter -- "Whiskey Lullaby" runs the gamut from alcoholism to love and loss -- the song was a commercial and critical hit, winning Song of the Year at the 2005 CMA Awards.

<p>This classic Loretta Lynn and Conway Twitty duet marked the duo's third #1 on the Billboard charts and was the title track of their 1973 album. With its characteristic country twang, Cajun influences, and upbeat vocals from these two country legends, "Louisiana Woman, Mississippi Man" remains a favorite among fans of traditional country. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/the_20_best_bad_movies_of_all_time/s1__30206336'>The 20 best bad movies of all time</a></p>

Richard E. Aaron/Redferns

"Louisiana Woman, Mississippi Man," Loretta Lynn and Conway Twitty

This classic Loretta Lynn and Conway Twitty duet marked the duo's third #1 on the Billboard charts and was the title track of their 1973 album. With its characteristic country twang, Cajun influences, and upbeat vocals from these two country legends, "Louisiana Woman, Mississippi Man" remains a favorite among fans of traditional country.

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<p>This legendary duet between then-couple Tammy Wynette and George Jones was a #1 hit in 1976 and remains one of the genre's finest vocal duets. It also offered a bit of a peek inside the duo's tumultuous marriage, which ended one year prior. </p>

Beth Gwinn/Redferns

"Golden Ring," Tammy Wynette and George Jones

This legendary duet between then-couple Tammy Wynette and George Jones was a #1 hit in 1976 and remains one of the genre's finest vocal duets. It also offered a bit of a peek inside the duo's tumultuous marriage, which ended one year prior.

<p>Reba McEntire enlisted back-up singer and incredible vocal talent Linda Davis for "Does He Love You," a dueling duet about two women arguing over the same man, in 1993. Later, Liza Minelli released her own version of the song as a duet with Patti LaBelle. </p>

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"Does He Love You," Reba McEntire and Linda Davis

Reba McEntire enlisted back-up singer and incredible vocal talent Linda Davis for "Does He Love You," a dueling duet about two women arguing over the same man, in 1993. Later, Liza Minelli released her own version of the song as a duet with Patti LaBelle.

<p>The first single from Tim McGraw's 1997 album "Everywhere," "It's Your Love" is a seriously compelling love ballad performed by one of country's most famous couples. McGraw's wife Faith Hill joins him here on the chorus, making for incredible harmonies and the kind of chemistry that can only come from two people who are legitimately in love. </p>

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"It's Your Love," Tim McGraw and Faith Hill

The first single from Tim McGraw's 1997 album "Everywhere," "It's Your Love" is a seriously compelling love ballad performed by one of country's most famous couples. McGraw's wife Faith Hill joins him here on the chorus, making for incredible harmonies and the kind of chemistry that can only come from two people who are legitimately in love.

<p>Waylon Jennings and Willie Nelson offer some solid parenting advice in "Mammas Don't Let Your Babies Grow Up To Be Cowboys," a catchy tune about the rough-and-tumble lives of cowboys everywhere. The classic track was a #1 hit and earned the duo a Grammy Award for Best Country Performance by a Duo or Group With Vocal in 1979. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/the_30_most_influential_drummers/s1__38466391'>The 30 most influential drummers</a></p>

Richard E. Aaron/Redferns

"Mamas Don't Let Your Babies Grow Up To Be Cowboys," Willie Nelson and Waylon Jennings

Waylon Jennings and Willie Nelson offer some solid parenting advice in "Mammas Don't Let Your Babies Grow Up To Be Cowboys," a catchy tune about the rough-and-tumble lives of cowboys everywhere. The classic track was a #1 hit and earned the duo a Grammy Award for Best Country Performance by a Duo or Group With Vocal in 1979.

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<p>Despite the decades-long collaboration between Dolly Parton and Porter Wagoner, "Please Don't Stop Loving Me" is the legendary duo's sole #1 hit. It was released in 1974 on "Porter n' Dolly," and remains a fan favorite. </p>

GAB Archive/Redferns

"Please Don't Stop Loving Me," Dolly Parton and Porter Wagoner

Despite the decades-long collaboration between Dolly Parton and Porter Wagoner, "Please Don't Stop Loving Me" is the legendary duo's sole #1 hit. It was released in 1974 on "Porter n' Dolly," and remains a fan favorite.

<p>Written by Bob Dylan, Johnny Cash and June Carter weren't yet married when they recorded "It Ain't Me Babe" in 1965. The song was an immediate hit and offered a peek into the couple's romantic future. They would be married just three years later, and go on to build one of the genre's most enduring legacies. </p>

Gijsbert Hanekroot/Redferns

"It Ain't Me Babe," Johnny Cash and June Carter

Written by Bob Dylan, Johnny Cash and June Carter weren't yet married when they recorded "It Ain't Me Babe" in 1965. The song was an immediate hit and offered a peek into the couple's romantic future. They would be married just three years later, and go on to build one of the genre's most enduring legacies.

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<p>This lament about the creeping influence of pop music on traditional country, originally recorded by bluegrass outfit Larry Cordle & Lonesome Standard Time in 1999, shot to fame that same year when Alan Jackson and George Strait performed "Murder on Music Row" on the CMA Awards. Even though it was never actually released as a single, Strait and Jackson's version hit #38 on the charts and later earned the duo two CMA Awards — one for Vocal Event of the Year, and another for Song of the Year. </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

Rick Diamond/Getty Images for George Strait

"Murder on Music Row," Alan Jackson and George Strait

This lament about the creeping influence of pop music on traditional country, originally recorded by bluegrass outfit Larry Cordle & Lonesome Standard Time in 1999, shot to fame that same year when Alan Jackson and George Strait performed "Murder on Music Row" on the CMA Awards. Even though it was never actually released as a single, Strait and Jackson's version hit #38 on the charts and later earned the duo two CMA Awards — one for Vocal Event of the Year, and another for Song of the Year.

<p>In 1994, powerhouse vocalist Pam Tillis teamed up with her father and country legend in his own right Mel Tillis for "Til All The Lonely's Gone." Part ode to Hank Williams, part hymn, the song is classic country at its finest. </p>

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"Til All The Lonely's Gone," Mel Tillis and Pam Tillis

In 1994, powerhouse vocalist Pam Tillis teamed up with her father and country legend in his own right Mel Tillis for "Til All The Lonely's Gone." Part ode to Hank Williams, part hymn, the song is classic country at its finest.

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<p>Despite its overtly racy title and country music's general sense of conservatism, Faith Hill and Tim McGraw found crossover success with "Let's Make Love" in 2000. It wasn't a #1 hit but did earn the duo a Grammy Award for Best Country Collaboration with Vocals. </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

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"Let's Make Love," Tim McGraw and Faith Hill

Despite its overtly racy title and country music's general sense of conservatism, Faith Hill and Tim McGraw found crossover success with "Let's Make Love" in 2000. It wasn't a #1 hit but did earn the duo a Grammy Award for Best Country Collaboration with Vocals.

<p>This 1993 chart-topper brought together Reba McEntire and Vince Gill, two of the most powerful vocalists in country music history. Originally, the plan was for McEntire to record "The Heart Won't Lie" with Kenny Rogers, but that fell through. Eventually, Gill was called in to record the other half, and the rest is history. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/every_razzie_worst_picture_winner_by_year/s1__31243484'>Every Razzie Worst Picture winner by year</a></p>

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"The Heart Won't Lie," Reba McEntire and Vince Gill

This 1993 chart-topper brought together Reba McEntire and Vince Gill, two of the most powerful vocalists in country music history. Originally, the plan was for McEntire to record "The Heart Won't Lie" with Kenny Rogers, but that fell through. Eventually, Gill was called in to record the other half, and the rest is history.

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<p>Written and recorded originally by Townes Van Zandt, Merle Haggard and Willie Nelson scored a #1 hit with "Pancho and Lefty" in 1983. It remains one of the genre's finest story songs and still inspires debate among fans about which story actually inspired Van Zandt to write the lyrics. Was it the life of Pancho Villa, or something more philosophical? </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

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"Pancho and Lefty," Willie Nelson and Merle Haggard

Written and recorded originally by Townes Van Zandt, Merle Haggard and Willie Nelson scored a #1 hit with "Pancho and Lefty" in 1983. It remains one of the genre's finest story songs and still inspires debate among fans about which story actually inspired Van Zandt to write the lyrics. Was it the life of Pancho Villa, or something more philosophical?

<p>Margaritaville mogul Jimmy Buffett and Alan Jackson teamed up in 2003 to record this legendary, island-inspired ode to day drinking. It was a massive crossover success for Jackson, charting at #17 on the all-genre Billboard Hot 100, and won the CMA Award that same year for Vocal Event of the Year. </p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/20_songs_that_should_have_won_a_grammy/s1__25413923'>20 songs that should have won a Grammy</a></p>

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"It's 5 O'Clock Somewhere," Alan Jackson and Jimmy Buffett

Margaritaville mogul Jimmy Buffett and Alan Jackson teamed up in 2003 to record this legendary, island-inspired ode to day drinking. It was a massive crossover success for Jackson, charting at #17 on the all-genre Billboard Hot 100, and won the CMA Award that same year for Vocal Event of the Year.

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<p>At the 2016 CMA Awards, R&B legend Beyonce teamed up with The Chicks to create what may be one of the finest live music performances in CMA history. This mash-up of Beyonce's "Daddy Lessons" and the Chicks's "Long Time Gone," the latter of which was a pointed reminder of the Chicks' lengthy absence from the country music charts, was the definition of entertaining. It was later released to streaming services. </p><p><a href='https://www.msn.com/en-us/community/channel/vid-cj9pqbr0vn9in2b6ddcd8sfgpfq6x6utp44fssrv6mc2gtybw0us'>Follow us on MSN to see more of our exclusive entertainment content.</a></p>

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"Daddy Lessons," The Chicks and Beyonce Knowles-Carter

At the 2016 CMA Awards, R&B legend Beyonce teamed up with The Chicks to create what may be one of the finest live music performances in CMA history. This mash-up of Beyonce's "Daddy Lessons" and the Chicks's "Long Time Gone," the latter of which was a pointed reminder of the Chicks' lengthy absence from the country music charts, was the definition of entertaining. It was later released to streaming services.

<p>There are few duos in country music more iconic than Loretta Lynn and Conway Twitty, and there are none cheekier than "You're The Reason Our Kids Are Ugly." "You're the reason our kids are ugly, little darling," the duo sings. "Ah, but looks ain't everything, and money ain't everything, but I love you just the same."</p><p>You may also like: <a href='https://www.yardbarker.com/entertainment/articles/the_20_most_iconic_episodes_of_spongebob_squarepants/s1__38867003'>The 20 most iconic episodes of ‘SpongeBob SquarePants’</a></p>

Michael Ochs Archives/Getty Images

"You're The Reason Our Kids Are Ugly," Loretta Lynn and Conway Twitty

There are few duos in country music more iconic than Loretta Lynn and Conway Twitty, and there are none cheekier than "You're The Reason Our Kids Are Ugly." "You're the reason our kids are ugly, little darling," the duo sings. "Ah, but looks ain't everything, and money ain't everything, but I love you just the same."

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<p>Even though Shania's solo version of "From This Moment On" is likely the best-known, the duet with Bryan White made this tune a classic wedding track following its release in 1998. A was a top-ten hit in the U.S., Australia, Canada, and the U.K, it's still likely that you'll hear it at an occasional wedding every once in a while. </p>

Beth Gwinn/Redferns

"From This Moment On," Shania Twain with Bryan White

Even though Shania's solo version of "From This Moment On" is likely the best-known, the duet with Bryan White made this tune a classic wedding track following its release in 1998. A was a top-ten hit in the U.S., Australia, Canada, and the U.K, it's still likely that you'll hear it at an occasional wedding every once in a while.

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