Special Report

Best Country Music Duets of All Time

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What’s better than a country song sung by your favorite performer? How about one sung by two of them, in perfect harmony? Country music has produced a number of memorable duets pairing husbands and wives, fathers and sons, fathers and daughters, and combinations of artists from other genres. (Sometimes the pairings push the envelope. Here are 25 bizarre musical collaborations.)

To assemble a list of the best duets in country music history, 24/7 Tempo reviewed listings of Grammys and Country Music Awards and nominations in pertinent categories, as well as lists of best country duets on sites including Wide Open Country, Country Thang Daily, Everything Nash, Spin Ditty, Yardbarker and Ranker, then curated the list to represent key figures and hit songs in traditional, modern mainstream, and alt.country categories from the past 71 years.

Duets that have paired some of country music’s finest performers – from Patsy Cline to Dolly Parton to Kenny Chesney – have been a staple of the genre. Keeping it in the family, the husband-and-wife team Chris and Morgane Stapleton turned “You Are My Sunshine” – the state song of Louisiana – into an affirmation of family and partnership. Through the use of technology, the late Hank Williams and his son, Hank Jr., were reunited in a music video, singing “There’s a Tear in My Beer.” (These are the greatest country music stars of all time.)

While many country songs are about poverty, love lost, personal demons, and redemption, others have addressed broader issues. Alan Jackson and George Strait used the song “Murder on Music Row” to decry the commercialization of country music and how that has disconnected it from its roots. Eric Church and country and blues singer Rhiannon Giddens teamed up to perform  “Kill a Word” following messages of hate and intolerance during the 2016 presidential election.

Click here to see the best duets in country music history

Country music is known for its various sub-genres, and the country rap theme burst onto the music scene in a big way in 2019 when “Old Town Road,” performed by country singer Billy Ray Cyrus and rapper Lil Nas X, set chart records.

No list of duets would be complete without a mention of notable performers crooning about drinking. Among is Travis Tritt and Marty Stuart’s “The Whiskey Ain’t Workin’ .’’ Jackson and Jimmy Buffett’s “It’s Five O’Clock Somewhere” is as much a working-class lament as it is about happy-hour nirvana. 

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

Patsy Cline & Bobby Lord
> Song: (Remember Me) I’m The One Who Loves You
> Year of release: 1950

Patsy Cline, whose career was tragically cut short in a plane crash, performed “(Remember Me) I’m The One Who Loves You” with country crooner Bobby Lord at the Grand Ole Opry.

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Source: David Redfern / Getty Images

Hank Williams & Hank Williams Jr.
> Song: There’s a Tear in My Beer
> Year of release: 1950/1988

The father/son duet is represented on this list by Hank Williams and Hank Willliams Jr. The elder Williams recorded “There’s a Tear in My Beer” originally around 1950 but did not release it. It came out only in 1989, 36 years after he died. The younger Williams got the demo to the unreleased song and added his vocals. In the official music video, Hank Jr. is recording the song in the studio, and he’s interrupted by his dad’s voice. The silhouette of the elder Williams is behind a closed door and the two sing together.

Source: Michael Ochs Archives / Getty Images

Johnny Cash & June Carter
> Song: Jackson
> Year of release: 1967

What many consider country music’s First Couple, Johnny Cash and June Carter collaborated on “Jackson.” It was co-written by Billy Ed Wheeler, who said he was partly inspired by the fighting of the husband and wife in Edward Albee’s play “Who’s Afraid of Virginia Woolf.” The song won a Grammy award for Best Country and Western Performance, the first of Cash’s 13 Grammy wins.

Source: David Redfern / Redferns via Getty Images

Loretta Lynn & Conway Twitty
> Song: Louisiana Woman, Mississippi Man
> Year of release: 1973

Loretta Lynn and Conway Twitty had great chemistry and recorded several duets. One of them was “Louisiana Woman, Mississippi Man,” which went to No. 1 on the Hot Country Song chart on Billboard. They were two-time winners of The American Music Award for Favorite Duo.

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Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

Kris Kristofferson & Rita Coolidge
> Song: Lover Please
> Year of release: 1974

A year after they were married, Kris Kristofferson and Rita Coolidge released “Lover Please” – a country take on the 1962 R&B hit sung by Clyde McPhatter. They made three duet albums together and they won the Grammy Award for Best Country Vocal Performance by a Duo or Group in 1974.

Dolly Parton & Porter Wagoner
> Song: Please Don’t Stop Loving Me
> Year of release: 1974

Dolly Parton and Porter Wagoner collaborated on 20 songs, but “Please Don’t Stop Loving Me” was their lone No. 1 on the Hot Country Songs list. The duet would be one of four country chart-toppers for Parton in 1974. She’s had 25 overall.

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Source: Michael Ochs Archives / Getty Images

Waylon Jennings & Willie Nelson
> Song: Mamas, Don’t Let Your Babies Grow Up to Be Cowboys
> Year of release: 1975

Frequent collaborators Waylon Jennings and Willie Nelson were a big part of the outlaw country music trend in the mid-1970s. They got together for the song “Mamas, Don’t Let Your Babies Grow Up to Be Cowboys” that would top the Hot Country song chart in 1978 for four weeks. They shared a Grammy for Best Country Performance by a Duo or Group with Vocal.

Source: Andrew Putler / Getty Images

Tammy Wynette & George Jones
> Song: Golden Ring
> Year of release: 1976

Tammy Wynette and George Jones, who were married from 1969 to 1975, recorded many duets and the passion in their relationship infused many of their collaborations. Among them was “Golden Ring,” one of three duet efforts that topped the Hot Country Songs chart on Billboard.

Source: Hulton Archive / Getty Images

Emmylou Harris & Roy Orbison
> Song: That Lovin’ You Feelin’ Again
> Year of release: 1980

Emmylou Harris paired with Roy Orbison in 1980 for the single “That Lovin’ You Feelin’ Again” that climbed to No. 6 on the Hot Country Songs chart on Billboard and was a crossover hit on Billboard’s Adult Contemporary list. Harris has had seven chart-toppers on the country chart.

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Source: Rick Diamond / Getty Images

Dolly Parton & Kenny Rogers
> Song: Islands in the Stream
> Year of release: 1983

Two of the biggest country stars of all time, Dolly Parton and Kenny Rogers, combined for memorable duets. None surpassed their first collaboration, “Islands in the Stream,” which reached No. 1 on Billboard’s Hot Country and Adult Contemporary charts. It was written by the Bee Gees and intended for Marvin Gaye. The song succeeded not only because of how Rogers’ gruff voice complemented Parton’s sweet vocals, but because of their obvious chemistry.

Source: Michael Ochs Archives / Getty Images

Willie Nelson & Merle Haggard
> Song: Pancho and Lefty
> Year of release: 1983

“Pancho and Lefty” has been covered by various artists. Willie Nelson and Merle Haggard’s version topped the Hot Country Songs chart on Billboard in 1983 and they adopted it for the title of their collaborative album. The song is about Pancho, a Mexican bandit, and his associate, Lefty, who betrayed him to the Mexican police.

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Source: Michael Ochs Archives / Getty Images

Dwight Yoakum & Buck Owens
> Song: Streets of Bakersfield
> Year of release: 1988

“Streets of Bakersfield” was recorded by Buck Owens in 1973 and 15 years later, he collaborated with Dwight Yoakam to make it a hit. It was one of 21 Hot Country Songs No. 1’s for Owens. The song became Yoakam’s first Hot Country Song chart-topper. Bakersfield, Calif., is famous as the location for the first subgenre of country music influenced by rock and roll, and Owens was one of its pioneers.

Travis Tritt & Marty Stuart
> Song: The Whiskey Ain’t Workin’
> Year of release: 1991

Travis Tritt and Marty Stuart combined for three duets in the 1990s and their most successful was “The Whiskey Ain’t Workin’ ,’, which reached No. 2 on the Hot Country Songs chart on Billboard.

Source: Paul Natkin / Getty Images

Reba McEntire & Vince Gill
> Song: The Heart Won’t Lie
> Year of release: 1993

Longtime friends Reba McEntire and Vince Gill ended up collaborating on “The Heart Won’t Lie” after Kenny Rogers and McEntire could not find the right range for their voices on the song. The McEntire/Gill version spent two weeks atop the Hot Country Songs chart on Billboard in 1993. Gill, who was supposed to sing harmony, stepped up and helped make the song a hit.

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Source: Rick Diamond / Getty Images

Tanya Tucker & Delbert McClinton
> Song: Tell Me About It
> Year of release: 1993

In 1993, Tanya Tucker and Delbert McClinton combined to record “Tell Me About It,” which reached No. 4 on Billboard’s Hot Country Songs chart.

Source: Jim Steinfeldt / Michael Ochs Archives via Getty Images

Garth Brooks & Trisha Yearwood
> Song: In Another’s Eyes
> Year of release: 1997

Country hit machine Garth Brooks – he’s had 19 Hot Country No.1s on Billboard – got to No. 2 with Trisha Yearwood with “In Another’s Eyes” in 1997. The song won Grammys for Best Country Collaboration with Vocals and Best Country Song. The song was one of six of their collaborations and they eventually got married in 2005.

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Source: Jason Kempin / Getty Images

Faith Hill & Tim McGraw
> Song: It’s Your Love
> Year of release: 1997

Speaking of married singing collaborations, Faith Hill and Tim McGraw have combined for memorable musical moments, such as “It’s Your Love.” The ballad topped the Hot Country Songs chart on Billboard for six weeks, and was one of five of their collaborations to land in the Hot Country top 10.

Source: Frazer Harrison / Getty Images

John Prine & Iris DeMent
> Song: In Spite of Ourselves
> Year of release: 1999

John Prine and folk/country singer Iris DeMent combined for an unfiltered, no-nonsense love song titled “In Spite of Ourselves.” It reached No. 5 on Billboard’s Hot Rock and Alternative Songs chart in April 2020, the month Prine died from Covid-19.

Source: William Campbell / Sygma via Getty Images

Vince Gill & Patty Loveless
> Song: My Kind of Woman / My Kind of Man
> Year of release: 1999

Vince Gill, who also appears on this list with Reba McEntire, was paired with Patty Loveless on “My Kind of Woman / My Kind of Man.” The song got to No. 27 on the Hot Country Songs chart in 1999.

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Source: Tim Mosenfelder / Archive Photos via Getty Images

Alan Jackson & George Strait
> Song: Murder on Music Row
> Year of release: 2000

“Murder on Music Row,” sung by Alan Jackson and George Strait, bemoaned the end of authentic country music, sacrificed in the quest for worldwide fame. The song only reached No. 38 on Billboard’s Hot Country chart. However, its performance at the County Music Association’s awards won it the Vocal Event of the Year award.

Source: David Redfern / Getty Images

Mel Tillis & Pam Tillis
> Song: Waiting on the Wind
> Year of release: 2001

The father/daughter combo performed “Waiting on the Wind,” a song about what a father and daughter mean to each other. It was the last track on Pam’s seventh studio album, “Thunder and Roses,” which climbed to No. 24 on U.S. Billboard Top Country Albums.

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Source: R. Diamond / WireImage via Getty Images

Alan Jackson & Jimmy Buffett
> Song: It’s Five O’Clock Somewhere
> Year of release: 2003

Jimmy Buffett, no stranger to drinking songs (“Margaritaville”), joined Alan Jackson on this one, “It’s Five O’Clock Somewhere.” The song was a huge hit, topping the Hot Country Songs chart on Billboard for eight weeks.

Source: Paul Hawthorne / Getty Images

Brad Paisley & Alison Krauss
> Song: Whiskey Lullaby
> Year of release: 2004

On the subject of drinking songs, Brad Paisley and Alison Krauss’s “Whiskey Lullaby” rose to No. 3 on the Billboard Hot Country Songs chart. It also won the 2005 Country Music Association Song of the Year award and went platinum two times.

Source: Michael Ochs Archives / Michael Ochs Archives via Getty Images

George Jones & Dolly Parton
> Song: The Blues Man
> Year of release: 2005

Another collaboration between George Jones and Dolly Parton resulted in “The Blues Man.” It was written by Hank Williams Jr., and tells the story about a singer who has been through some tough times. He admits his mistakes and says he’s turned his life around.

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Source: Christopher Polk / Getty Images Entertainment via Getty Images

Kenny Chesney & Grace Potter
> Song: You and Tequila
> Year of release: 2011

Grammy-nominated Kenny Chesney, who has nine chart-topping albums on the Billboard 200, collaborated with Grace Potter about the song likening how tequila gets into your bloodstream like a lover gets into your soul. The song reached No. 3 on the Hot Country chart on Billboard.

Source: Hulton Archive / Getty Images

Don Williams & Alison Krauss
> Song: I Just Come Here for the Music
> Year of release: 2012

Alison Krauss, already on this list for pairing with Brad Paisley, provided backing vocals and fiddle music for the ballad “I Just Come Here for the Music” on Don Williams’ LP “And So It Goes.” The rich-voiced Williams, known as “the Gentle Giant,” was one of country music’s most venerable performers.

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Source: Rick Diamond / Getty Images

Miranda Lambert & Carrie Underwood
> Song: Somethin’ Bad
> Year of release: 2014

Two of country top music’s female vocalists combined in 2014 for the duet “Somethin’ Bad.” It topped the Hot Country Songs chart on Billboard and appeared on Lambert’s top-selling album “Platinum.” The song was originally intended as a duet between a man and a woman.

Linda Ronstadt & Joe Ely
> Song: Where Is My Love
> Year of release: 2014

During her long and well-regarded career Linda Ronstadt has had collaborations with Dolly Parton, Emmylou Harris, the Nelson Riddle Orchestra, and Aaron Neville among others. Joe Ely, the acclaimed Texas songwriter and singer, has crossed into other genres, too, performing with Bruce Springsteen, Uncle Tupelo, Los Super Seven, The Chieftains, and The Clash. Ronstadt and Ely teamed up for “Where is My Love” in 2014.

Source: Christopher Polk / Getty Images Entertainment via Getty Images

Eric Church & Rhiannon Giddens
> Song: Kill a Word
> Year of release: 2016

Eric Church decided to release “Kill a Word,” featuring Rhiannon Giddens, as a single to address messages of hate and intolerance during the 2016 presidential election. In an interview with Rolling Stone, the singer said it was time to get out the message. The song was performed on the 2016 Country Music Association Awards and the “Tonight Show with Jimmy Fallon.” Giddens is a founding member of the Grammy-winning country and blues group the Carolina Chocolate Drops.

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Source: Debra L Rothenberg / FilmMagic via Getty Images

Kenny Chesney & Pink
> Song: Setting the World on Fire
> Year of release: 2016

“Setting the World on Fire” is a country rock song by Kenny Chesney and edgy rocker Pink. It topped the Hot Country Songs chart in August 2016.

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Chris Stapleton & Morgane Stapleton
> Song: You Are My Sunshine
> Year of release: 2016

Husband-and-wife team Chris Stapleton and Morgane Stapleton reimagined the song written in 1939 often sung as a children’s lullaby and turned it into a forceful affirmation of family. The song appeared on the compilation album “Southern Family.”

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Source: Rachel Murray / Getty Images

Maren Morris & Vince Gill
> Song: Dear Hate
> Year of release: 2017

Country music singer-songwriter Maren Morris released “Dear Hate,” featuring country music legend Vince Gill, in response to the tragedy at the Route 91 Harvest Festival in Las Vegas where 60 people were slain in the largest mass shooting in U.S. history. Maren, who performed at the event, had written the song three years before the incident, but made it available to digital-service providers for purchase and/or streaming within 24 hours of the shooting. Maren said all of her proceeds from “Dear Hate” would be donated to Las Vegas nonprofits for the needs of victims.

Source: John Shearer/Country Rising / Getty Images

Keith Urban & Carrie Underwood
> Song: The Fighter
> Year of release: 2017

Keith Urban, the Australian-born country singer, has amassed 16 country chart-toppers. He didn’t get to the summit with Carrie Underwood, but he was close with “The Fighter,” which topped out at No. 2 on the Hot Country Songs chart of Billboard. The single was certified double platinum in August 2019 by the Recording Industry Association of America, with combined sales and streaming units of over 2 million units in the US.

Source: Kevin Winter / Getty Images Entertainment via Getty Images

Lil Nas X & Billy Ray Cyrus
> Song: Old Town Road
> Year of release: 2019

With country singer Billy Ray Cyrus and rapper Lil Nas X on vocals, “Old Town Road” shook up music genres in 2019. In September 2021, the song set the record as the highest-certified song ever by the Recording Industry Association of America with 15-times platinum status in the US, meaning it sold 15 million units. It has sold over 18 million records worldwide and is one of the best-selling singles ever.

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Source: Michael Buckner / Getty Images

Rodney Crowell & Lyle Lovett
> Song: What You Gonna Do Now
> Year of release: 2021

Texas compatriots and fellow Grammy winners Rodney Crowell and Lyle Lovett combined to perform “What You Gonna Do,” a cut from Crowell’s album “Texas,” an LP about all things, well, Texas. The album cracked Billboard’s top-50 in top album sales.

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