Highways, Heartaches & Hope: An Emmylou Harris Playlist

At the 60th Grammy Awards, The Recording Academy will honor Emmylou Harris with a Lifetime Achievement Award, recognizing her remarkable four-decade-long career, which has led to the creation of one of Americana music’s most ethereal, iconoclastic songbooks.

The first time I heard Emmylou’s voice, it was in the role for which she first became known: as a harmonizing partner. Linda Ronstadt’s landmark 1975 album, Heart Like A Wheel, which boasts one of the most perfect flip-side sequences ever, features Emmylou on the gorgeous “I Can’t Help It (If I’m Still In Love With You).” Emmylou sings just behind Linda’s soaring, full-bodied wail, swooping into the harmony as if she were a robin or a magpie flying in from a Spring afternoon. Not long after their first duet, Emmylou released her debut album, establishing herself as a first-class interpeter, songwriter and vocalist, carrying the torch of the cosmic, genre-bending Americana style first articulated by her lover and mentor, the late Gram Parsons. To listen to Emmylou Harris is to listen in on the sound of a woman’s soul; her voice so intimately and intensley relates the pains of heartbreak, nostalgia and loss, that it is as if she’s speaking right from her heart, unaware that anyone’s there to hear. Sometimes, her voice breaks off into a whisper, the rest of the lyric falling into the ether. Other times, her crystaline soprano will crack, the way glass shatters, delicately but somehow still full of beauty. Her gift is singular, and yet, the sound of her voice relates feelings universal and ancient. Years after first hearing her, I still stop to marvel when I hear Emmylou’s voice. Songs I’ve heard over and over again still bring my world to a pause when I hear them.

Since her debut, Emmylou has released a string of nearly perfect records. She’s reinvented her sound several times, reflecting on country music’s past while bringing it’s core themes into the present. Each record is full of songs that are plaintive, achingly alive, seemingly willed into existence by the fact that they had to be there, because things of such beauty simply have to exist.

In order to celebrate this more-than-deserved recognition, I’ve tried to pick one song from each of her records that is, arbitrarily, “the best.” So, this is a tour through Emmylou’s songbook, curated by a devoted fan and shaped by his tastes. In the process, I’ve had to slight some songs on some records that are far from being “runner ups.” If anything, these songs are a highway through the vast open plains of Emmylou’s career. But, as any fan of an artist like Emmylou will tell you, the best way to travel through these plains is by taking as many detours, unplanned exits and sudden swerves off the main road as you can.

“Boulder To Birmingham” — Pieces of the Sky (1975)

Has there ever been such a perfect song about losing someone you love? One of the few songs penned by Emmylou on first few albums, “Boulder to Birmingham” flows to the movements of a heart in mourning, and the longing and desperation are palpable in her voice. “The hardest part is knowing I’ll survive,” she sings, before wishing the highway could turn into an ocean and carry her away. A song that feels like it must have existed since time immemorial, it evokes an almost biblical sense of loss.

“Til I Gain Control Again” — Elite Hotel (1975)

Although she’d covered emerging songwriter Rodney Crowell on her debut, Emmylou truly inhabits his lyrics for the first time on this track from Elite Hotel. Crowell is to Emmylou what Dylan was to Baez, and this tender, melancholy number is a testament to their unique bond as singer and songwriter.

“Pancho & Lefty” — Luxury Liner (1976)

Country music fans will tell you that Willie Nelson and Merle Haggard recorded the defintive version of Townes Van Zandt’s epic, sumblime tale about the two titular outlaws, but after hearing Emmylou’s version, you’ll have no choice but to disagree. This is, for me, Emmylou’s best vocal performance. It’s revelatory and stunning, like the sight of the first sunlight in the wide open desert. Emmylou’s empathetic reading renders the shapes of Van Zandt’s narrative into images of vivid color, with Crowell’s guitar further bringing the characters into focus. It’s always reminded me of Robert Altman’s The Last Picture Show, probably because, by the time the end rolls around, it’s made your heart swell with emotions you simply could not have predicted you’d feel when it started. I think it may be her masterpiece.

“Leaving Louisiana In Broad Daylight” — Quarter Moon In a Ten Cent Town (1978)

A slice of classic folk-inspired country storytelling, this accordian-driven number is a rollicking, stomper of a song. Cinematic and witty, it’s the centerpiece of a fantastic, but otherwise quiet, album. Not only is it just downright fun, but this tale of a quirky Louisiana bayou town is also about the timeless desire we all have to break out on our own, and to follow our heart’s every whim and desire.

“Hickory Wind” — Blue Kentucky Girl (1979)

One of Gram Parson’s greatest contributions to the American songbook, Emmylou tackles this sorrowful tune with unsurpassed nuance. The way she animates nostalgia here is something to behold: her voice strains as it swells in its lower registers, and it sounds like she’s holding onto each word and note as if they’re memories from the woods of South Carolina.

“The Boxer” — Roses In The Snow (1980)

Though she’d always incorprated the sounds of classic country in her music, with this 1980 record Emmylou turned to more traditional, bluegrass-inspired fare, including tracks from the Louvin Brothers and the Carter Family. But the record’s standout is a cover of Paul Simon’s “The Boxer,” which features a gorgeous ensemble of harmonizing vocals in its chorus, courtesy of Linda Ronstadt and Dolly Parton. It’s short, sweet and catches you by surprise, because for a second you can’t quite place where you’ve heard the song before. Only Joan Baez also has this unique ability: to make a song seem like it came from a time before it was made.

“Ashes By Now” — Evangeline (1981)

Emmylou simmers and sears on this decidedly-modern rendition of another Crowell classic. It chugs and crawls along to it’s explosive chorus, in which a double-tracked Emmylou rings in defiant yet vulnerable. There’s even synthesizers chiming in alongside a sultry electric guitar. Not your usual Emmylou, but a gem nonetheless.

“The Last Cheater’s Waltz” — Cimarron (1981)

Though it’s a somewhat uneven album, being that it’s composed mostly of outtakes, Cimarron does feature some gorgeous songs, including this one. It reminds me of the kind of cheatin’ songs Reba McEntire would perfect in the 1980’s, with it’s melodramatic strings, a wailing pedal steal guitar, and a soapy tale of aching hearts and broken homes.

“Racing In The Streets” — Last Date (1982)

It should come as a surprise to no one that Emmylou’s voice was a marvel to behold live. Her first concert album is on par with her greatest studio LPs, and it features her take on what is arguably Bruce Springteen’s masterpiece: “Racing In The Street,” from Darkness on the Edge of Town. Springsteen’s tale of a man who takes to drag racing to avoid the crushing boredom of modernity is both deft social critique and introspective character study. Emmylou’s vocal is informed by these dual intentions, and she sings Springsteen’s story with a kind of dedication and might that almost threatens to break open her voice. She excavates and tunnels into the song, and by the end, a single reading of the word “street” becomes a wailing cry of such perfect sorrow that it is matched only by animals lost in the wild.

“On The Radio” — White Shoes (1983)

An album full of oddities (including a cover of “Diamonds Are A Girl’s Best Friend”), White Shoes is home to Emmylou’s most unexpected cover: Donna Summer’s “On The Radio.” Giving into the rasps and cracks of her voice, I think this cover is important for the fact that it proves how Donna Summer’s disco was more than just music to move your feet to: it was also musically and emotionally strong, with a beating heart at its core. Leave it to Emmylou to find that heartbeat and sing it into the world.

“Sweetheart of the Rodeo” — The Ballad of Sally Rose (1985)

A semi-autobiographical concept album that draws on her relationship with Gram Parsons for it’s overaching narrative, The Ballad of Sally Rose was the first Emmylou record to feature mostly her own compositions, and it’s a marvel. Structurally taut and featuring an auetuer’s attention to detail, the album’s centerpiece is this song, which again features backup by Linda and Dolly. It’s a mythical story about a singer looking for his muse, worn weary by the road but hopeful that an angel will come to bring him grace. The way Emmylou sings the word “sorrow” in the opening line would be enough to make this song a serious addition to her cannon.

“My Father’s House” — Thirteen (1986)

Another gorgeous Springsteen composition, Emmylou makes this a full-blooded country song. When I hear it, I picture her on the porch of an old house in the middle of the country, with grey skies above and storm clouds gathering just beyond the horizon. As the song builds to it’s end, Emmylou has so fully travelled through the narrator’s regret and suffering, that you’re left open-mouthed, unable to imagine the singer of this song didn’t experience every word of it before sat down to write it.

“Someday My Ship Will Sail” — Angel Band (1987)

In her entire catalogue, this to me is the only Emmylou Harris record without a standout track. It’s a singular exception, a record of hers I don’t take much interest in. Again composed of mostly traditional, gospel and bluegrass songs, Emmylou’s delivery is stellar throughout, but there’s a lack of passion and creativity which make all her other records such exciting listens from start to finish.

“The Pain of Loving You” — Trio (1987)

Kicking off the spectacular collabration record between her, Dolly Parton and Linda Ronstadt, Emmylou’s voice has never sounded sweeter than on this Wagoner/Parton track. The meeting of three voices at their peak, “The Pain of Loving You” demonstrates how Emmylou’s voice could function as a sturdy foundation, while also being flexible enough to hallow itself out to be filled with other voices. Here, these ladies form a choir of angels, and you can almost see them in a wide open field, singing amongst the sounds of nature and history.

“A River For Him” — Bluebird (1989)

Hinting at the atmospheric, etheral style which would become the hallmark of her later career, this song, penned by Emmylou, opens with a mournful piano, and will instantly remind of Jeff Buckley’s “Hallelujah.” Her voice sails into the open sky, unadorned and naked, as the gentle melody unfolds beneath it. It’s something of a funeral waltz, a procession of a woman’s pain which seems to have no clear destination in mind. And yet it finally does arrive at its last chorus, which is filled with a choir of angelic voices. It ends with a single bell tolling, a conclusion both magnificent and understated.

“Tougher Than The Rest” — Brand New Dance (1990)

Nothing gets me like girls singing The Boss, and Emmylou does it with such flare and heart. It’s a redeeming number on a somewhat subpar record, where Emmylou’s commanding vocal subverts the machismo of Springsteen’s flirtatious boasting.

“Lovin’ You Again” — Cowgirl’s Prayer (1993)

This is a song that shouldn’t work. On first listen, it’s just too slow. It doesn’t build the way you expect it to, and the lyrics come off as too simple, too direct. Then, you listen more closely, and suddenly you’re swept off your feet, transfixed by every word Emmylou is uttering. It’s a song that beguiles you, confuses you, stirs something inside you that isn’t plainly obvious. It’s an accomplishment of the highest order, that Emmylou so entirely envelops the words and so acutely projects the emotions hidden between them. Without realizing it, this song will have you starting to question how the heart works the way it does. When she sings “I know there’ll be another time, so until then,” I find myself longing for that song, where Emmylou will meet her love once more.

“Blackhawk” — Wrecking Ball (1995)

Wrecking Ball changed the course of Emmylou’s career, and with it’s unconventional production courtesy of Daniel Lanois, it just about created contemporary alternative country. It’s a record that flows together, the textured drums and distorted guitars creating a soundscape for Emmylou’s noticeably wearier, fragile voice. Picking one song from the bunch takes away from the album’s power, but for me “Blackhawk” is something special on its own. Another story song about young lovers, it manages to be incredibly detailed about its protagonists while maintaining a profound sense of mystery and wonder.

“You’ll Never Be The Sun” — Trio II (1999)

Though the second Trio album wasn’t nearly as terrific as its predecessor, it did give Emmylou a chance to return to a more organic, folky country sound, evident on this simple, acoustic song. I love how it manages to convey both sadness and anger, but channels them subdued, in a moody, quiet rage.

“Michaelangelo” — Red Dirt Girl (2000)

That it took so long into Emmylou’s career to get an album full of her own poetry is a crime. “Michaelangelo” is a sprawling, unyielding dirge, as sparse as it is dense with allusions, emotions and evocations. There’s a decidedly mystical tone to her lyrics, and her voice is in its own spiritual register, speaking to its titular character in a way that suggests that he might be a Saint, or a Pagan God, or perhaps a spirit she’d met in her dreams.

“Strong Hand (For June)” — Stumble Into Grace (2003)

Consider this alongside Roseanne Cash’s masterpiece record Black Cadillac, as both bring humanity and grace to the mythos of Johnny and June Cash. A tender tribute and a reflection on the lasting power of love, “Strong Hand” is reminiscent of a church hymn. Except in Emmylou’s theology, the miracle is “how one soul finds another.”

“Belle Star” — All The Road Running (2006)

A duet from her collaborative album with Mark Knopfler, “Belle Star” is a slightly funky love song, celebrating the reckless and freewheeling devotion between a woman who wants to be the “Belle star” to her man’s “Jesse James.”

“Moon Song” — All I Intended To Be (2009)

Composed by Patti Griffin and featuring the McGarrigle sisters in the background, “Moon Song” is a lament sung from the heart of a pining, lovelorn wanderer. Something of a cross between a Celtic folk song and a barroom ballad, it finds Emmylou regretful, mourning for all the time spent following her lover down dead-end roads and waiting alone outside on winter nights. Emmylou’s graceful embrace of the sorrow that comes with lost time, something she so excellently explores all across her late-career records, gives this song a timeless quality. Alone in a closing bar, she begs for time to go easy on her, and wishes only for the moon to follow her home, a last chance at companionship on the lonliest of journeys: the walk back to our homes, emptied of love and hope, where we await for the day to come though it won’t bring anything new. It sounds almost pathologically melancholic, but its strangely cathartic, and Emmylou’s voice shines like a light in the story’s darkest moments.

“The Ship On His Arm” — Hard Bargain (2011)

A stunningly dense and literary ode to a lover away at war, I suggest pairing this with another epic story of lovers seperated by battle, Roseanne Cash’s “When The Master Calls The Roll.” Both are tributes to the both the fragile bonds between lovers that can so easily be broken by the reality of our mortality. The narrator believes that kissing the ship on her lover’s arm will somehow keep him safe, that she can somehow embed her love into the ink which decorates his skin. It’s a gesture that, as a listener, you want so desperately to believe; that we can perform small miracles every day that keep our loved ones safe from harm’s way.

“Spanish Dancer” — Old Yellow Moon (2013)

Since her first record, Rodney Crowell has been a constant presence on Emmylou’s albums, providing not just brilliant songs but an indelible musical energy. In 2013, the duo finally teamed up for an LP-length collaboration, and it contains this marvelous gem written by Springsteen’s wife, Patti Scialfa. Old Yellow Moon is the first record where Emmylou sounds truly aged, her voice a little weaker, less robust, but still incredibly expressive, full of even more defined nooks, crannies and textures. Singing to her mother about the electric way a man can send fires throughout your entire body, Emmylou sounds as if she’s reflecting on a life’s worth of lovers, realizing that life may age you but it doesn’t take away that thing inside which makes us suseptible to the charms of another. When did her mother realize that men are not “fantastic jewels” that we’re not worthy of, but just another part of the ebbs and flows of life? It reminds me of a song that might have been sung by Eva Peron in Evita, with its Latin-flavored acoustic plucking and easy rhythm.

“Her Hair Was Red” — The Traveling Kind (2015)

The narrator of this song from Emmylou & Crowell’s second collaborative LP goes to an island to the place where her grandmother gave birth to her father, a black and white picture in her hand of this woman whom she didn’t know but whose energy courses through her. “There’s so much you wouldn’t know about her,” looking at the photograph, not her pain, her happiness nor her red hair or blue eyes. It’s true that Emmylou always exhibited an empathy which seemed foreign to her youthful years, but she could only have aged into this type of song. Her voice doesn’t need to soar the way it did forty years earlier to find the emotions embedded into this song. This record actually does come at the forty year mark of her debut, and that highway, from Boulder to Birmingham and back again, would naturally leave Emmylou inside a song like this, reflecting on the past while knowing that today will continue to turn into tomorrow.

As a bonus, here’s some non-album tracks by Emmylou to fill out this already expansive, deeply emotional rollercoaster ride through her incredible catalogue of songs:

“Like An Old Fashioned Waltz” & “Waltz Across Texas Tonight — Alternate Versions” from Songbird: Rare Tracks and Forgotten Gems. The former, written by Sandy Denny and originally from White Shoes, boasts a jaw-dropping vocal and an eerily romantic wind instrument accompanying Emmylou. The latter is one of Emmylou’s best lyrics, written with Crowell, and has surfaced as an outtake from both Cowgirl’s Prayer and Wrecking Ball.

“Western Wall” from Emmylou’s collaborative album with Linda Ronstadt, Western Wall: The Tucson Sessions, written by the one and only Roseanne Cash. A song that marvels at the divine beauty of the world around us, it has Linda singing a painfully perfect falsetto alongside Emmylou’s sturdy soprano.

“Love Hurts” from Grievous Angel, the last album Gram Parsons recorded before his death. Slow and simmering, this duet balances Parsons and Harris almost equally, singing to each other as much as to the listener. It’s the best example of what made their pairing so special: two entirely different interpretations of the same lyrics, played simultaneously, somehow ending up in perfect harmony.