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The Best Steve Earle Songs

By Hal Horowitz

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Everyone is familiar with the first wave of country “outlaws” (Waylon, Willie, Guy Clark, etc.), but Steve Earle, a generation removed from them, has been every bit as rebellious and rambunctious.

Over a recording career that began in 1986 and shows no sign of slowing down, he’s proven to be eclectic and prolific, releasing two dozen albums that span country, bluegrass, blues, rock and folk, sometimes mixed together, all tethered by a gutsy voice and an edgy attitude that’s as steadfastly free from BS as any artist of his stature.

Here are 20 examples of Earle at the top of his craft.

20
Holler Country Music

Indieblu Music | 2004

Courtesy of artist

Both Warren Zevon and Earle shared a distrust of doing things the traditional way in the music business. This Zevon cover, included in 2004’s wonderful posthumous various artist tribute to the twisted West Coast singer/songwriter, Enjoy Every Sandwich, finds Earle backed by country rockers Reckless Kelly as he pleads for a romantic interest to take him back pledging “I swear that I changed since then”.

Holler Country Music

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19
Holler Country Music

Steve Earle under exclusive license to Warner Records | 2017

So You Wannabe an Outlaw

This title track to 2017’s album is a cautionary rocker for anyone who thinks the outlaw musician’s life is a worthy career choice. “If you wanna be an outlaw, so you better think twice… you can never go home” he warns as the Dukes stomp behind him adding a musical exclamation point to his adamant rant.

Holler Country Music

Steve Earle under exclusive license to Warner Records | 2017 ? videoThumbnail.image_asset.caption : ''}

18
Holler Country Music

Concord Music Group | 2016

You Were On My Mind

The cover of this 60s folk-pop hit (originally by the We Five) from 2016’s under-the-radar Earle/Shawn Colvin duet album, was produced by Buddy Miller. Its mix of originals and versions of older tunes like ‘Ruby Tuesday’ found both participants in frisky spirits, especially on this upbeat minor hit, the most streamed tune from a release that deserved more exposure.

Holler Country Music

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17
Holler Country Music

Warner Records | 1995

Goodbye

Earle returned from drug addiction and a jail sentence that sidelined him since 1990 with 1995’s acoustic Train a Comin’. Recorded for an independent label after MCA dropped him, the bittersweet ballad is a remembrance of a love gone sour. It resonated with Emmylou Harris who quickly covered it for her Wrecking Ball album the same year.

Holler Country Music

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16
Holler Country Music

Harlem River Blues

In a fog of heartbreak after losing his son Justin Townes Earle, a significant singer/songwriter in his own right, to a drug related death, his father recorded 2021’s J.T. covering his son’s songs. The elder Earle goes bluegrass for this rather upbeat tune, seemingly about suicide, where the singer lets the dirty water cover him. Steve’s version features fiddle and a gospel chorus.

Holler Country Music

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15
Holler Country Music

Steve Earle under exclusive license to Warner Records | 1999

The Mountain

Earle hired the Del McCoury Band to accompany him on this 1999 bluegrass career side trip. That group’s traditionalism didn’t synch with Earle’s more recalcitrant nature and the combination was notoriously fraught with personality clashes. That’s not to discount how musically successful it was (even nominated for a Grammy in the bluegrass category), exemplified by this title track sung from the vantage point of a coal worker reflecting on his life in the mines, a topic Earle would later revisit. 

Holler Country Music

Steve Earle under exclusive license to Warner Records | 1999 ? videoThumbnail.image_asset.caption : ''}

14
Holler Country Music

New West | 2007

Satellite Radio

The most popular entry on 2007’s love letter to New York City, Washington Square Serenade, was produced by the Dust Brothers’ John King. He brings a contemporary feel which almost has Earle rapping about being a DJ on the titular service, wondering who else in the galaxy can hear him, over an intriguing mix of funky programmed drums and sparkling acoustic guitars.

Holler Country Music

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13
Holler Country Music

MCA | 1986

Someday

This deeper selection from Earle’s critically acclaimed 1986 debut combines the Springsteen concepts of leaving town with no specific destination, a rustic sensibility and personal lyrics seemingly ripped from his journals. “I wanna get out of here to see what’s over the rainbow” he sings with a youthful vocal twang, tremolo heavy guitar and just enough pedal steel to push this strummy ballad into country rock territory.

Holler Country Music

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12
Holler Country Music

Geffen | 1990

The Other Kind

Anyone bold enough to name their live album Shut Up and Die Like an Aviator is throwing down a gauntlet. So it goes for Earle’s first (of many) concert discs. This 1991 contract filler appeared before his firing from MCA, a five year sabbatical to deal with a drug addiction, along with other career derailing issues. His voice is all kinds of ragged which mirrored his many health related problems, but this room filling, thumping rocker with its declaration of individuality was made for arenas.

Holler Country Music

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11
Holler Country Music

New West | 2020

Black Lung

You needn’t have seen or even known about the stage play Coal Country for which Earle created the music, titling the resulting album The Ghosts of West Virginia to appreciate this riveting set. ‘Black Lung’ is an appropriately dark journey into the lives of coal miners. He rasps through the daily routine of its protagonist accompanied by a swampy, ominous string band as he wheezes “Black Lung never gets better/Every breath gets a little harder to draw”. Intense, even for Earle.

Holler Country Music

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10
Holler Country Music

New West | 2011

Meet Me in the Alleyway

Earle goes Tom Waits for this seething entry from 2011’s I’ll Never Get Out of This World Alive. Although the disc’s title hearkens back to Hank Williams’ song of the same name, Earle doesn’t cover it. He instead wrote originals like this that convey a life on the fringes of an urban jungle, accompanied by nightmarish, thumping drums, distorted vocals, raw harmonica and a portentous edge miles away from anything

Holler Country Music

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9
Holler Country Music

Warner Records | 1996

Hard Core Troubadour

If you needed to sum up Earle’s career in one song, this 1996 track fit just fine. Country rocking, ringing guitars, a killer riff and vocals singing about the life he had led, albeit in the third person. “Baby what you waiting for?” he asks the woman he’s leaving, without an ounce of pity. Tough and real like Springsteen whose Rosalita makes a brief appearance in the final verse.

Holler Country Music

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8
Holler Country Music

Steve Earle under exclusive license to Warner Records | 2000

The Galway Girl

This acoustic love, perhaps infatuation is a better description, song written about Joyce Redmond who also plays the Bodhran on Earle’s 2000 recording, displays his affection for traditional Irish music and of the country itself. Among Earle’s most covered songs (mostly by Irish artists), it was not surprisingly a huge hit in Ireland and is his third most streamed track on Spotify, despite not being released as a single in the States.

Holler Country Music

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7
Holler Country Music

Warner Records | 1996

Feel Alright

The title track and the opening of Earle’s 1996 second comeback release returned him to a major label (Warner Brothers), a tougher electric sound and hence a larger audience. It’s clearly autobiographical with Earle rocking out and snarling “Be careful what you wish for friend / Because I've been to hell and now I'm back again” with the intensity of someone who has done exactly that.

Holler Country Music

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6
Holler Country Music

MCA | 1986

Hillbilly Highway

One of the highlights from Earle’s 1986 debut perfectly encapsulates his ability to recount a private story and make it universal. It tells of his father who needed to leave home to discover life and how that affected his own future. The chorus is catchy, the words are honest and a terse twang guitar solo brings it alive.

Holler Country Music

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5
Holler Country Music

MCA Records | 1987

I Ain’t Ever Satisfied

The title of this 1987 twang rocker says is all. It’s sung by a guy who has been married seven times and honest enough to hold up a mirror, taking a long hard look at himself. The song starts like a sensitive ballad but quickly shifts to a tougher vibe. Once the chorus kicks in, it’s impossible not to sing along. Various live versions capture the lyrical fervor better than the somewhat tame original from his second album.

Holler Country Music

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4
Album - Steve Earle - Copperhead Road

Uni Records | 1988

Snake Oil

A honky tonk piano starts this Copperhead Road tune which quickly transforms to a rugged guitar rocker as Earle sings about phony cure-alls meant to fleece unsuspecting buyers. “Well ain’t your president good to you?” he asks, knowing the answer, as the band pounds along behind him. It seems politicians are still selling that stuff, which makes this so timeless.

Album - Steve Earle - Copperhead Road

Uni Records | 1988 ? videoThumbnail.image_asset.caption : ''}

3
Holler Country Music

WARNER RECORDS | 1997

Taneytown

Hang on for this 1997 El Corazon slow burner that could easily have been a Neil Young/Crazy Horse obscurity. It’s another tale of escaping a drab hometown for something different, although this time the singer is black and the subject of a lynching gone wrong. The taut, hotwired guitars power the harrowing drama and intensity of the story into a Drive-By Truckers-styled audio tornado.

Holler Country Music

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2
Holler Country Music

MCA | 1986

Guitar Town

“Hey pretty baby are you ready for me?”, asks Earle on the opening title track from his 1986 debut. It’s a perfect way to introduce the rambling, and restless, young troubadour. A featured reverbed guitar riff captures the deep country in his music and when he sings about following a voice down the lost highway, he’s predicting his future.

Holler Country Music

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1
Album - Steve Earle - Copperhead Road

Uni Records | 1988

Copperhead Road

Earle’s most streamed composition by a wide margin was the opening salvo on 1988’s third album. The song about a family of moonshiners starts with bagpipes styled keyboard, leading into Earle’s hard strummed mandolin. Everything gradually builds until detonating at 2:30 into its volatile main section. The harder edged rock nipping at the edges of his first two releases explodes here with a resounding punch to the gut. Its crossover popularity on rock radio should have been the beginning of superstardom, but Earle’s drug problems suspended his career for five years, losing any momentum the tune and album created.

Album - Steve Earle - Copperhead Road

Uni Records | 1988 ? videoThumbnail.image_asset.caption : ''}

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