Fifty Favorite Country Duets of All-Time

When your reader base consists of about twenty people, you can honor their requests fairly easily. An anonymous person commented that they would like to see me do a countdown of the best country duets of all-time. As I replied in the comments, all-time countdowns make me a little nervous. I started listening to country music in 1991, so I’m sure there are a lot of great, obscure duets that I never heard from before that time. So I’m being cautious and just calling this my Favorite Country Duets list.

In the interest of clarity and consistency, I have limited the list to collaborations between individual artists, so music by established duos such as Brooks & Dunn or Big & Rich are not eligible. Additionally, there must be legitimate lead vocals by both artists. If one artist is simply providing harmony, it doesn’t count as a duet in my book; there must be at least one line in the song sung by each artist. Finally, it’s a duet list, so any collaborations of three or more, no matter how stellar they may be (Sorry, Trio) are not eligible.

I also avoided checking out CMT’s list on the same topic to ensure my choices were free of outside influence. Hopefully, anonymous and everybody else will enjoy this latest list…

Fifty Favorite Country Duets
of All-Time

#50
“In Another’s Eyes”
Trisha Yearwood & Garth Brooks

Two cheating spouses remorse over the fact that the trusting spouses they are cheating on would never suspect they’re running around. The irony that this was released when the currently engaged Yearwood & Brooks were still in their former marriages is delicious.

#49
“Down From Dover”
Nancy Sinatra & Lee Hazlewood

When she sings, it’s campy; when he sings, it’s creepy. This half-hilarious, half-disturbing cover of the Dolly Parton classic “Down From Dover” has to be heard to be believed.

#48
“Pancho and Lefty”
Willie Nelson & Merle Haggard

It originally appeared on the classic Luxury Liner set from Emmylou Harris, but the Nelson & Haggard cover is a classic unto itself. The two men get into the psyche of a renegade and the lawmaker who finally tracks him down, with glorious results.

#47
“Somewhere In The Vicinity Of The Heart”
Shenandoah & Alison Krauss

Shenandoah always kept one toe in bluegrass, so it made perfect sense for them to pair up with then-unknown Alison Krauss for this sweet ballad of two jaded souls finding new love at a downtrodden cafe. This was Krauss’ breakthrough and Shenandoah’s last big hit.

#46
“Keep Walkin’ On”
Faith Hill & Shelby Lynne

A damn near Pentecostal gospel rave-up, the girls praise the Lord with sass and style.

#45
“I Walk The Line (Revisited)”
Rodney Crowell & Johnny Cash

Crowell recounts his childhood discovery of the music that would define his life, taking us back to the beat-up car in which he first heard Johnny Cash sing “I Walk The Line.” The Man in Black himself provides the chorus, which alters the melody of his signature hit.

#44
“Hopelessly Yours”
Lee Greenwood & Suzy Bogguss

Another case of an established star’s last hit and a rising star’s breakthrough, Bogguss steals the show in this simple ballad of hopeless love.

#43
“You’re The Reason Our Kids Are Ugly”
Conway Twitty & Loretta Lynn

One of the funniest records in country music history, the chemistry between these two was never more playful on record.

#42
“I Don’t Care”
Bobbie Cryner & Dwight Yoakam

You wanna hear some hillbilly? The muddy twang by these two traditional singers will make city-dwellers cringe if they don’t already have a taste for such unfiltered southern drawl.

#41
“Good News, Bad News”
George Strait & Lee Ann Womack

George has some good news; he’s worked through his issues and is ready to take Lee Ann back. Lee Ann has some bad news; she’s already moved on to someone new. This brought both of them good news at this year’s CMA awards, winning them the trophy for Musical Event of the Year.

#40
“Rockin’ Years”
Dolly Parton & Ricky Van Shelton

Ever the opportunist, Parton has always found time to record with the biggest stars of any given time. In 1991, that was Ricky Van Shelton. This sentimental declaration of eternal love was her last #1 hit.

#39
“If You Don’t Wanna Love Me”
Cowboy Troy & Sarah Buxton

This record works because of Buxton’s hauntingly sweet vocal, which gives the gravity and emotional subtext necessary to sell the listener on Troy’s storytelling.

#38
“The Way We Make A Broken Heart”
John Haitt & Rosanne Cash

This was left unreleased until ten years after being recorded, long after Cash had already recorded the song again as a solo number and scored a #1 hit with it. As a duet, the song is darker and more calculated, as the guilt-ridden one-sided conversation of Cash’s hit is instead a two-sided conversation of two plotting adulterers almost reveling in the pain they are causing the man sitting at home, wondering where his wife is.

#37
“Who Says You Can’t Go Home”
Bon Jovi & Jennifer Nettles

It’s barely been sent to radio, but this collaboration between the Sugarland lead vocalist and Bon Jovi absolutely soars. Nettles not only stands her ground against a legendary band, she actually takes control of the record, her soulful vocals providing the high points of a very entertaining performance.

#36
“Louisiana Woman, Mississippi Man”
Conway Twitty & Loretta Lynn

Fun, silly, and a bit of a tongue-twister, two lovers won’t let the Mississippi river keep them from each other. Twitty’s even willing to wrestle an alligator to get to Loretta. If I were him, I’d be more worried about Mooney.

#35
“Something Up My Sleeve”
Suzy Bogguss & Billy Dean

Using a surprisingly effective magician metaphor, Bogguss & Dean lament that there are no tricks, spells or surprises that can keep the two of them together anymore.

#34
“It’s Five O’Clock Somewhere”
Alan Jackson & Jimmy Buffett

Jackson is a legend partly because his drinking anthems are as good as his deep and meaningful ballads. Despite a concept of time zones that doesn’t quite work (if it’s half past twelve, it’s not five o’clock anywhere), this hit got everybody drinking in the afternoon with a little less guilt. Okay, maybe just me.

#33
“Brotherly Love”
Keith Whitley & Earl Thomas Conley

I don’t know if I’ve ever heard another song this beautiful about the bond between two siblings. What “Calico Plains” is for sisters, this is for brothers.

#32
“Shelter From The Storm”
Rodney Crowell & Emmylou Harris

Rodney had the brilliant idea to make a Bob Dylan classic a duet with a few lyric changes, and bring in Emmylou Harris to sing it with him. The result is a fascinating, rambling collaboration that is chill-inducingly beautiful.

#31
“Party For Two”
Shania Twain & Billy Currington

You can keep “From This Moment On” – everybody knows that record was much better once she ditched Bryan White and sang it solo. But here, Twain and Currington provide an irresistably catchy and sexy flirtation that radiates off of the record.

#30
“Squeeze Me In”
Garth Brooks & Trisha Yearwood

Recorded previously by Lee Roy Parnell and its writer Delbert McClinton, Brooks & Yearwood have the good wisdom to make it a duet that brings out a ferocious performance from both.

#29
“‘Til All The Lonely’s Gone”
Pam Tillis & Mel Tillis

Pam Tillis was so well-established by the time she recorded Sweetheart’s Dance that she could have her dad sing a few lines of her gospel closing track without having to worry about standing in his shadow. Mel helps out respectably, giving the family-themed song a little boost, but even he knows to stay out of the way once it’s time for those big notes; Pam tears the roof off as Daddy watches.

#28
“Don’t Cry Joni”
Conway Twitty & Joni Lee

Speaking of Dad and daughter duets, Twitty had his daughter Joni Lee sing on one of his records. Radio found it buried on the album and started playing it. If you can ignore the fact that it’s dad and daughter singing, you’ll be deeply touched by this tale of an older man breaking the heart of the young girl who adores him, then realizing he loves her once it’s too late.

#27
“Please Remember Me”
Aaron Neville & Linda Ronstadt

Somewhere between writer Rodney Crowell releasing this and Tim McGraw making a smash of it, Neville & Ronstadt got together to make a duet out of one of the greatest country songs ever written. Now, you know the song is great; it’s being sung by two of the most talented vocalists in the history of recorded music. Do I have to tell you it’s a classic performance?

#26
“Mendocino County Line”
Willie Nelson & Lee Ann Womack
1991
Peak: #7

I still don’t really understand what the hell they’re talking about in this song, but Nelson & Womack make beautiful music together.

#25
“Does He Love You”
Reba McEntire & Linda Davis

Two of the wimpiest women ever to appear in a country song wonder who he really loves – his wife or his mistress. Why they don’t just talk about why they’re even dealing with such an asshole is beyond me, but who can deny the power of the performances of these two ladies?

#24
“Don’t Go Out”
Tanya Tucker & T. Graham Brown

Two friends try to talk each other out of the dates they’ve planned independently, since they secretly are in love with each other. It’s a raw back and forth by two equally gritty vocalists.

#23
“Baby Don’t Go”
Dwight Yoakam & Sheryl Crow

Yoakam & Crow cover Sonny & Cher and put the beatnik legends to shame in the process.

#22
“Keep Your Eyes On Jesus”
Pam Tillis & Johnny Cash

The voice of God meets the voice of an angel. Tillis sings the gorgeous lyrics and melody of this Louvin Brothers classic in her sweet soprano as Cash reads the bible verses that inspired the song.

#21
“Mamas Don’t Let Your Babies Grow Up To Be Cowboys”
Waylon Jennings & Willie Nelson

An indisputable classic cowboy anthem, the reluctant Outlaws essentially counsel against mothers raising their boys to end up like them.

#20
“Not Too Much To Ask”
Mary Chapin Carpenter & Joe Diffie

One would think the label must have forced a collaboration between such distinctly different artists, but with a fantastic song, courtesy of Miss Carpenter, there was no going wrong. Diffie sounds fantastic, even though he’s removed from his usual honky-tonk setting, and Carpenter is downright wistful as she sings her cautiously optimistic lyrics.

#19
“Two Story House”
George Jones & Tammy Wynette

Recorded years after their marriage split up, Jones & Wynette lament that they focused on fame and fortune, working to make the money to afford the two-story house of their dreams, and now are in a beautiful home, but there’s no love to be found there.

#18
“The Last Thing On My Mind”
Porter Wagoner & Dolly Parton

They released tons of duets, but this first single release from Porter & Dolly remains their most interesting pairing. The thinly veiled indifference to his feelings as she’s leaving is surprisingly harsh – “I could’ve loved you better, didn’t mean to be unkind”, Parton says in a sing-song voice that lacks any hint of remorse.

#17
“Baby Ride Easy”
Carlene Carter & Dave Edmunds

The duo try on different fantasies ranging from truck stop chef and waitress to president and first lady, and commit to stay with each other if his loving is good and her cookin’ ain’t greasy.

#16
“Crying”
Roy Orbison & k.d. lang

The original solo recording of Orbison’s was a classic, but he took the song to a new level when he recorded it again with the assistance of then-new singer k.d. lang. Her soaring vocals give the song a new intensity.

#15
“After The Fire Is Gone”
Conway Twitty & Loretta Lynn

Their first collaboration is one of their best, a somber and honest assessment of why people cheat – “Love is where you find it when you find no love at home, and there’s nothing cold as ashes after the fire is gone.”

#14
“It’s Such A Small World”
Rodney Crowell & Rosanne Cash

A very modern one-night stand, this is something of an up-tempo “I May Hate Myself In The Morning” minus the guilt, a hooking up with an old lover – “You and me will always be looking for something that already happened”, they sigh. But for one night, all is new again, as a chance run-in in New York City becomes a night of passion between a man who has lived alone for a while and woman who feels like she’s gone out of style.

#13
“By My Side”
Lorrie Morgan & Jon Randall

Morgan and Randall observe that there are so many people who put up walls that keep them from falling in love because they’re too scared they’ll get hurt, but vow to each other that “I’m not gonna be afraid to give up my heart that way, cause I need you by my side. I’m not gonna say I’m strong out here in this world alone, cause I need you by my side.” One of those records that makes you want to fearlessly fall in love for the three minutes it plays.

#12
“The Battle Hymn Of Love”
Kathy Mattea & Tim O’Brien

It sounds much more like an Irish wedding song than a country hit. This list of heartfelt vows to stay together for better or worse is what you’d expect from any record involving Mattea: tasteful, sentimental and the honest truth.

#11
“Helping Me Get Over You”
Travis Tritt & Lari White

Tritt and White acknowledge that their new lovers are just there to fill a void. They haven’t gotten over each other, and their new man/woman are serving the purpose of getting past a love that kicked them in the ass.

#10
“A Bad Goodbye”
Clint Black & Wynonna

Black wonders how he can leave the woman that they both know he’s been bound to leave, if he can’t do it with a smile. He cares enough about her that he doesn’t want to leave her with “a bad goodbye.” By the time they both sing, “How can we be so far between where we are and one more try?”, even the listener suspects that goodbye isn’t the answer.

#9
“The Heart Won’t Lie”
Reba McEntire & Vince Gill

Two of country music’s most distinctive vocalists absolutely bare their souls on this power ballad. All the lies they tell to the world and themselves won’t stop the fact that the heart won’t lie, and their hearts are telling them they belong together.

#8
“Whiskey Lullaby”
Brad Paisley & Alison Krauss

This dark and harrowing tale of a double suicide via Jack Daniels is already a standard. Paisley has never sounded better, but it’s Krauss’ ghostly vocals that lift this into a spiritual experience.

#7
“The Sweetest Gift”
Linda Ronstadt & Emmylou Harris

A mother visits her son in prison, giving him the sweetest gift of all – a mother’s unconditional love. It’s a song as old as the ages, but Ronstadt & Harris recorded the definitive version, their intertwining vocals conjuring up a long-gone era of mountain soul.

#6
“Portland, Oregon”
Loretta Lynn & Jack White

Dripping with sexual tension and cheap beer, the worlds of traditional country and alternative rock collide, producing a dead-on portrait of alcohol-induced lust on the west coast.

#5
“Islands In The Stream”
Kenny Rogers & Dolly Parton

This song makes absolutely no sense. Having acknowledged that, this duet is a legendary meeting of two country superstars at the peak of their pop crossover fame. That lovers across the country felt like islands in the stream just listening to them is a testament to their on-record charisma and innate ability to turn a confusing lyric into an anthem of love.

#4
“Golden Ring”
George Jones & Tammy Wynette

A tale of a wedding ring that by itself is “just a cold metallic thing”, this golden ring travels from the pawn shop to the wedding chapel, becoming the symbol of a couple’s love. As things fall apart, and “they fight their final round”, she declares “one thing’s for certain, I don’t love you anymore,” and throws the ring off of her finger. By the time the ring finds its way back to the pawn shop, its adventure has left the listener wondering if love can ever be for all eternity.

#3
“Streets of Bakersfield”
Dwight Yoakam & Buck Owens

A brilliant collaboration between mentor and student, Yoakam revisits a song by his idol and invites him to sing on the new recording. The Bakersfield sound is given its finest tribute by being granted new vitality. It’s one of the finest achievements of both men, no small feat given their respective accomplishments. Now that they are both legends, the value of this pairing is ever higher in retrospect.

#2
“September When It Comes”
Rosanne Cash & Johnny Cash

This was the audio documentary of Johnny Cash’s final days on earth, not “Hurt.” Rosanne writes and sings a fascinating reflection on preparing for a parent’s impending death. She writes a near-eulogy for her father to sing that feels unflinchingly honest – “I cannot move a mountain now, I can no longer run; I cannot be who I was then. In a way, I never was.” This is Johnny the human and the father, not Cash the legend and icon. Listening to the obvious love between father and daughter, it’s hard not to think he was even more important in his family life than he was in his music.

#1
“As Soon As I Hang Up The Phone”
Conway Twitty & Loretta Lynn

Only in country music, and possibly only in the 1970’s, could a record as brilliantly hokey as this find the audience it deserved. It starts with a telephone ring, and Loretta picks up the phone. For half of the record, Lynn is so happy that Conway has called her, as the talk around town is that he’s leaving her: “You gave me the will to go on as soon as I picked up the phone.” He’s trying to get a word in edgewise, and the listener is already aware that the rumors are true.

When he finally tells her halfway through that “Oh but it is true. They’re not wrong,” she lets out a wail that only a country fan can love – “Oh nooooo, oh nooooo, I can’t believe that it’s true.” Then Conway the cad surfaces, throwing every line at her that a cheating man will – ” I know you know that I never thought it would come to this” and “I really thought that I loved you, you know that” and “You just got to believe me, I never meant to hurt you” and “This is the hardest thing I ever had to do, and it hurts me too.” Lynn wails back, “You tell me it’s over and done, you say that you’ve had all your fun”, and is choking back the tears as she sings, “I can’t believe you’ll be gone as soon as I hang up the phone.”

The listener is left feeling like a voyeur by the time they hear the dial tone, as if they’ve eavesdropped on a very private conversation of a woman being left by a heartless man. Legend has it that one country fan was so incensed by Conway’s dumping of Loretta on this record that she slapped Conway in the face for being so cruel, not realizing it was only a song. Even Twitty appreciated such an illustration of the effectiveness of the performance, despite his stinging cheek. The raw energy of this collaboration makes it, by a wide margin, my favorite country duet of all-time.