Love Hurts: The 50 Best Country Duets

It takes two to tango, two to fall in (and out of) love, and two to sing songs of heartbreak and loss. Country music has a long and revered history of duets – and what magnificent pairings there have been. George Jones and Tammy Wynette; Jim Reeves and Patsy Cline; Johnny and June Carter Cash; Porter Wagoner and Dolly Parton; and Robert Plant and Alison Krauss. These giants of music are just a few of the wonderful duos in our list of the 50 best country duets.

Listen to the best country duets on Spotify.

50: Loretta Lynn and Conway Twitty – Lead Me On

“Knowing Conway Twitty has been one of the greatest pleasures in life,” said Loretta Lynn. The pair shared an amazing chemistry, showcased on country music duets such as 1970’s “Lead Me On.” They were two-time winners of The American Music Award for Favourite Duo.

49: Dwight Yoakam and Sheryl Crow – Baby Don’t Go

Dwight Yoakam’s 1997 album “Under the Covers” featured songs by the Beatles, the Kinks and Sonny & Cher’s “Baby Don’t Go.” Yoakam teamed up with Sheryl Crow – one of the biggest female stars of the 1990s – to deliver a rousing new version of this 1960s hit.

48: Striking Matches – When the Right One Comes Along

Striking Matches is an American duo consisting of guitarist-songwriters Sarah Zimmermann and Justin Davis. One of their best compositions, “When the Right One Comes Along,” was also a key part of the soundtrack for the hit television show Nashville.

47: Crystal Gayle and Eddie Rabbit – You and I

The versatile Crystal Gayle once did a whole duet album with Tom Waits. In 1982, she had a hit with the late Eddie Rabbitt on the romantic country-pop song “You and I,” penned by the acclaimed Nashville songwriter Frank J Myers.

46: George Strait and Lee Ann Womack – Good News, Bad News

Veteran George Strait’s voice subtly blends with Lee Ann Womack, and Stuart Duncan’s wonderful fiddle playing adds to the appeal of the delicate country love song “Good News, Bad News.” The song appeared on Strait’s 2005 album “Somewhere Down in Texas.”

45: Bobbie Gentry and Glen Campbell – All I Have to Do Is Dream

There have been few better harmony pairings than the Everly Brothers, who made the song “All I Have to Do Is Dream” world famous. In 1968 singer-songwriter Bobbie Gentry and Glen Campbell recorded their own sweet version of the classic written by Boudleaux Bryant.

44: Alan Jackson and George Strait – Murder on Music Row

“Murder on Music Row” was a 1999 song that lamented the death of “real” country music. When Alan Jackson and George Strait sang it at the County Music Association’s awards that year, they were handed the ‘Vocal Event of the Year’ award. Their subsequent studio version was released as a B-side to Strait’s single “Go On” and it became a cult radio hit.

43: Vince Gill and Dolly Parton – I Will Always Love You

Dolly Parton had some strange duet partners over the years – including actors Burt Reynolds and Sylvester Stallone – but one of her best collaborations was with Vince Gill. In 1995 they had a chart hit with an affecting duet version of Parton’s 1973 classic “I Will Always Love You.”

42: Lady A and Stevie Nicks – Golden

Back in the days when Lady A were still called Lady Antebellum, the band recorded a 2014 duet version of their song “Golden” with Fleetwood Mac’s Stevie Nicks. “I love Lady Antebellum, and to me, this song is their “Landslide” because it’s just that spectacular,” Nicks said at the time.

41: The Judds – Love Can Build a Bridge

Naomi Judd co-wrote the sweet ballad “Love Can Build a Bridge” and her duet version with sister Wynonna won a Grammy in 1992 for ‘Best Country Performance by a Duet’.

40: Rodney Crowell and Rosanne Cash – It’s Such a Small World

Tammy Wynette and George Jones are just one example of a husband-and-wife singing partnership who flourished together musically. When Rodney Crowell was married to Rosanne Cash, they recorded the stirring country music duet “It’s Such a Small World,” which was the lead single to Crowell’s hit 1988 album “Diamonds & Dirt.”

39: Kenny Rogers and Kim Carnes – Don’t Fall in Love with a Dreamer

Kim Carnes was a noted backing singer (she appears in the documentary 20 Feet from Stardom) and she co-wrote the sparkling power ballad hit “Don’t Fall in Love with a Dreamer,” which she sang with Kenny Rogers on the 1980 album “Gideon.”

38: Dwight Yoakam and Buck Owens – Streets of Bakersfield

Homer Joy composed “Streets of Bakersfield” after trudging round the California town in new cowboy boots and getting blisters. He offered the song to Buck Owens, who recorded it in 1973. In 1988, 59-year-old Owens revisited the song in a duet with Dwight Yoakam. Their new version was a Grammy-winning No1 hit.

37: Gretchen Peters and Bryan Adams – When You Love Someone

Gretchen Peters has written regularly with Bryan Adams over the years – and they sang together on the impressive Everlys-styled duet “When You Love Someone,” which Adams originally sang solo over the final credits of the Sandra Bullock film Hope Floats.

36: Willie Nelson and Lee Ann Womack – Mendocino County Line

Elton John’s magnificent songwriting partner Bernie Taupin co-wrote the lyrics for “Mendocino County Line,” which was a 2002 duet for Willie Nelson and Lee Ann Womack. Her sweet voice melded well with Nelson’s raspy delivery, and the song won a Grammy for Best Country Collaboration.

35: Shania Twain and Bryan White – From This Moment On

The 1997 hit “From This Moment On” had unusual origins. Twain came up with it while attending a football match in Italy with her husband. “My mind drifted and I started writing,” she said. Although Elton John was initially proposed as her singing partner, Twain picked Bryan White, whom she described as “the best male voice in country music.”

34: Anne Murray and Glen Campbell – I Say a Little Prayer/By the Time I Get to Phoenix

In 1971, Anne Murray and Glen Campbell had the inspired idea of teaming up and recording joint versions of songs that had been hits for them as solo stars. The most successful was their medley of these songs by Burt Bacharach & Hal David and Jimmy Webb respectively.

33: Tim O’Brien and Darrell Scott – House of Gold

The inventive harmonies and subtle phrasings of Tim O’Brien and Darrell Scott gave new life to “House of Gold,” the Hank Williams classic about the evils of greed.

32: Aaron Neville and Linda Ronstadt – Please Remember Me

Bringing together people from different musical genres and backgrounds can work well. This was the case when New Orleans soul and R&B singer Aaron Neville teamed up with country legend Linda Ronstadt, and the pair shine on “Please Remember Me,” a tender love song co-written by Rodney Crowell.

31: John Prine and Iris DeMent – In Spite of Ourselves

The late great John Prine released a 2016 album of duets called “For Better, Or Worse,” which featured Lee Ann Womack, Holly Williams and Kacey Musgraves, among others. Prine had a gravelly voice that worked splendidly linked to the rich, gospel-based tones of Iris DeMent. Prine’s song “In Spite of Ourselves” is one of the most richly comic in country music.

30: Kris Kristofferson and Rita Coolidge – From the Bottle to the Bottom

In 1973, Kris Kristofferson and Rita Coolidge, who were recently married, released a duet album called “Full Moon,” which included his song “From the Bottle to the Bottom.” “Harmony came easily for both of us, and it hadn’t gotten to where we were fighting – yet,” said Kristofferson. The song won a Grammy in 1974. Six years later they were divorced.

29: Alison Krauss and James Taylor – How’s the World Treating You

Chet Atkin’s song “How’s the World Treating You” has been covered by stars such as Elvis Presley and Sarah Vaughan. In 2007 Alison Krauss and the master singer-songwriter James Taylor collaborated on a mellow, yearning version of this 1950s classic.

28: Patty Griffin and Dierks Bentley – Beautiful World

Dierks Bentley co-wrote the uplifting song “Beautiful World” with his songwriting partner Brett Beavers, and had Patty Griffin in mind from the start as his singing partner on this 2009 single. “Her voice is one of a kind. Her voice adds some weight and gravity to the whole song, to kind of keep it rooted,” Bentley said.

27: Robby Hecht and Rose Cousins – Soon We Were Sleeping

Sometimes two voices fit in such a natural way that they bring authenticity to the song they are singing. This is the case with Robby Hecht and Rose Cousins’s moving version of a heartbreak song called “Soon We Were Sleeping.” The video for the song is cool, too.

26: Kenny Rogers and Sheena Easton – We’ve Got Tonight

“We’ve Got Tonite” was written by rock singer Bob Seger in the 1970s. When Kenny Rogers recorded his passionate duet version with Scottish pop singer Sheena Easton in 1983 he changed the spelling to “tonight” for the title of a cover version that shot to No1 on the country charts.

25: Steve Earle and Iris DeMent – I’m Still in Love With You

Iris DeMent has one of the most distinctive female voices in country music. As well as her great duets with Prine, she also collaborated in 1998 with Steve Earle on a fantastic bluegrass version of his song “I’m Still in Love With You,” backed by the brilliant Del McCoury Band.

24: Trisha Yearwood and Garth Brooks – In Another’s Eyes

When Trisha Yearwood and Garth Brooks had a hit with “In Another’s Eyes” in 1997 they were married to other spouses. They grew closer after their first Grammy-winning collaboration and eventually married each other in 2005. Brooks co-wrote “In Another’s Eyes” with Bobby Wood and John Peppard.

23: Nanci Griffith and Mac McAnally – Gulf Coast Highway

Nanci Griffith is a remarkable songwriter and she co-wrote the modern classic “Gulf Coast Highway” for her 1987 album “Little Love Affairs.” Her voice blends well with Mac McAnally, a record producer and successful solo artist in his own right, on this sorrowful masterpiece.

22: Loretta Lynn and Conway Twitty – As Soon as I Hang Up the Phone

“As Soon as I Hang Up the Phone” – a heartstring-tugging song about a woman trying to save a crumbling relationship – was a massive hit in 1974 for Lynn and regular partner Twitty. He performed his spoken word parts in a separate room at Bradley’s Barn studio in Tennessee, while on the phone to Lynn in the recording booth.

21: Rosanne Cash and Johnny Cash – September When It Comes

Rosanne Cash’s haunting song about preparing mentally for her father’s impending death was recorded with her famous father while he was in poor health. The great Man in Black died a few months after the release of the metaphor-filled “September When It Comes” in 1983.

20: Brad Paisley and Alison Krauss – Whiskey Lullaby

Country music is full of songs about the problems of drinking. “Whiskey Lullaby,” a potent duet between Brad Paisley and Alison Krauss, won the 2005 Country Music Association Song of the Year award and went platinum twice.

19: Roy Orbison and k.d. lang – Crying

David and Don Was produced the spine-chilling 1988 hit version of Roy Orbison’s own classic “Crying” that featured the 1960s star and Canadian activist singer k.d. lang. The pair met for the first time at the recording session and Orbison said they immediately struck up a “natural” partnership.

18: Dolly Parton and Porter Wagoner – The Last Thing on My Mind

“The Last Thing on My Mind” is songwriter Tom Paxton’s best known work. In 1967, the song was issued as the debut single from Porter Wagoner and 21-year-old Dolly Parton. It launched an uninterrupted string of top 10 hits for the duo that lasted for the following three years.

17: Loretta Lynn and Conway Twitty – Louisiana Woman, Mississippi Man

Lynn and Twitty provided another fine example of excellent close harmony singing on their 1973 version of “Louisiana Woman, Mississippi Man.” The song was produced by Owen Bradley, one of the creators of what was known as Nashville Sound in the 1950s.

16: Mark Knopfler and Emmylou Harris – Lost on the River

There is an interesting blend of country and folk on “Lost on the River,” a song that Hank Williams wrote and originally recorded as a duet with his wife Audrey. This version by country legend Harris and Dire Straits maestro Mark Knopfler, from the tribute album “Hank Williams Timeless,” contains some lovely mandolin from Mike Henderson.

15: Reba McEntire and Vince Gill – The Heart Won’t Lie

Reba McEntire and Vince Gill have been friends for half a century and their empathy helped make “The Heart Won’t Lie” – a 1992 single from the album “It’s Your Call” – a modern classic. Happenstance played its part in the success, because McEntire initially planned to record it with Kenny Rogers, but the pair couldn’t find a range that suited their voices. Gill, who had originally been down to just sing harmony, stepped up – and the result was special.

14: Don Henley and Dolly Parton – When I Stop Dreaming

Charlie and Ira Louvin, the renowned harmony duo the Louvin Brothers, recorded the scintillating “When I Stop Dreaming” in 1955. This magnificent heartbreak song has been covered hundreds of times, including 60 years later by Don Henley and Dolly Parton on the album “Cass Country.”

13: Tammy Wynette and George Jones – Golden Ring

Alison Krauss, a record-breaking Grammy-winner, was once asked her opinion on the best ever country duo. Unhesitatingly, she replied: “Take Me,” one of a score of awesome songs by George Jones and Tammy Wynette. There were so many classics from a pair who put such passion into their singing, a sound informed and inflamed by their own tempestuous relationship. “Golden Ring,” from 1976, is sublime.

12: Norah Jones and Dolly Parton – Creepin’ In

Dolly Parton has the sort of sweet, adaptable voice that allows her to excel as a duettist, whether she is singing with men (Willie Nelson, Randy Travis, Vince Gill, Don Henley) or with other women (Emmylou Harris, Carrie Underwood, Mindy Smith). In 2004, Parton and the silky-voiced Norah Jones gelled brilliantly on “Creepin’ In” for the album “Feels Like Home.”

11: Gillian Welch and Alison Krauss – I’ll Fly Away

As well as being a superb songwriter, Gillian Welch has popularised tunes from a bygone age, including the 1929 hymn “I’ll Fly Away.” Her scintillating version with Alison Krauss, for the Coen Brothers film O Brother, Where Art Thou?, was produced by the talented T-Bone Burnett.

10: Ray Charles and Willie Nelson – Seven Spanish Angels

Take two giants of modern music in Ray Charles and Willie Nelson, add a rousing song by Troy Seals and Eddie Setser and finish with top session musicians, such as trumpeter Bill McElhiney, and you have all the ingredients for a dazzling triumph. “Seven Spanish Angels” shot to No1 in the Billboard charts in 1984.

9: Johnny Cash and June Carter Cash – Jackson

One of the most celebrated music romances of all time was Johnny Cash and June Carter. The tempestuous lovers had a hit with “Jackson,” which co-writer Billy Ed Wheeler said was partly inspired by the fighting husband-and-wife in Edward Albee’s play Who’s Afraid of Virginia Woolf.

8: Bob Dylan and Johnny Cash – Girl from the North Country

“Johnny Cash was and is the North Star; you could guide your ship by him — the greatest of the greats,” said Bob Dylan. In 1969, Dylan revisited his gorgeous 1963 song “Girl from the North Country” and re-recorded it as a duet with his hero Cash.

7: Kenny Rogers and Dolly Parton – Islands in the Stream

“Islands was originally written by the Bee Gees for Marvin Gaye but then they asked me to do it. Barry Gibb asked Dolly Parton to sing with me. I give her full credit because that song was one of my career-making ones. The Bee Gees were so good at writing on the upbeat.” “Islands in the Stream,” a tear-jerking love song, sold more than two million copies in America.

6: Robert Plant and Alison Krauss – Please Read the Letter

Great country duets are not consigned to a bygone age. One 21st-century example of a masterful collaboration is the unlikely pairing of country great Krauss and former Led Zeppelin singer Robert Plant. On their brilliant 2007 album “Raising Sand,” producer T Bone Burnett recorded Krauss and Plant live to tape and had them sat in a booth, half-facing each other at a 45-degree angle. A number of songs were cut in one take, including “Please Read the Letter.”

5: Waylon Jennings and Willie Nelson – Mama Don’t Let Your Babies Grow Up to Be Cowboys

Willie Nelson and Waylon Jennings seemed so natural as a male singing partnership and their version of Ed Bruce’s song about the “cowboy life” became a popular classic when it was covered on their 1978 duet album. “Mama Don’t Let Your Babies Grow Up to Be Cowboys,” a deft song about loneliness and alienation, won the pair a Grammy for ‘Best Country Performance by a Duo or Group’.

4: George Jones and Tammy Wynette – Cryin’ Time

Some voices flow together like a blend of the finest whiskeys and the George Jones/Tammy Wynette duet version of “Cryin’ Time” – a Buck Owens tune memorably recorded by Ray Charles – is glorious. It was recorded in 1975, during a period when they were about to get divorced.

3: Don Williams and Emmylou Harris – If I Needed You

Sometimes the brilliance of a particular song itself can be the decisive factor in making a country classic. Some compositions just suit a duet interpretation. It would be hard to pick the definitive version of Townes Van Zandt’s gorgeous love song “If I Needed You,” because there have been fine versions by Carrie Rodriguez and Ben Kyle, Jason Isbell and Amanda Shires and Ricky Skaggs and Sharon White, among others. But it’s hard to beat the depth that Emmylou Harris and Don Williams brought to the song in 1981 for the MCA album “Especially for You.”

2: Patsy Cline and Jim Reeves – I Fall to Pieces

“I Fall to Pieces” was written by celebrated songwriters Hank Cochran and Harlan Howard. At first, Patsy Cline hated the sorrowful tale of a woman trying in vain to forget her lost love – and only reluctantly recorded a version that became a sensation. She died in a plane crash two years later. An overdubbed duet version featuring Jim Reeves – who was also killed in a plane crash – was released in 1982, when Chet Atkins mixed versions from both singers.

1: Gram Parsons and Emmylou Harris – Love Hurts

Gram Parsons was only 26 when he died of an overdose in 1973. Earlier that year, Parsons and Emmylou Harris had recorded a stunning version of “Love Hurts,” another magnificent song composed by Boudleaux Bryant, and also one made famous by The Everly Brothers. The Parsons/Harris version, which featured Al Perkins on pedal steel guitar, is an achingly sad country music duet.

Listen to the best country duets on Spotify.