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The Best Jerry Jeff Walker Songs

By Hal Horowitz

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Although Robert Clyde Crosby was born in upstate New York, upon relocating to Austin, Texas in the early 70s, he changed his name to Jerry Jeff Walker. That was the beginning of becoming a prominent artist whose edgy approach was newly tagged as “outlaw” or “cosmic cowboy” music. When Walker passed in 2020, his reputation was legendary.

Here is Holler's list of 20 of the best Jerry Jeff Walker songs.

20
Holler Country Music

Vanguard | 1969

Fading Lady

This bittersweet acoustic folk ballad was a highlight of Walker’s first major band, Circus Maximus.

It’s very much a relic of its time with echoes of Tim Buckley, Eric Anderson and Tim Rose, as Walker recounts the tale of a woman who married for money but now, later in life, is depressed and emotionally empty because of that decision.

Holler Country Music

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19
Holler Country Music

MCA | 1973

Gettin' By

The opening track from Walker’s 1973 career changing Viva Terlingua album encapsulates the lazy, bluesy, country lope, conversational vibe and overall laidback attitude for this then 30-year-old veteran.

The chorus of “Livin’ my life easy come, easy go” was perfect for clubs filled with fans enthusiastically singing along, making it an instant crowd favorite.

Holler Country Music

MCA | 1973 ? videoThumbnail.image_asset.caption : ''}

18
Holler Country Music

Tried & True Music | 1998

Gringo in Belize

One of a handful of songs Walker wrote about the Caribbean locale (others are ‘Down in Belize’ and ‘Come Away to Belize With Me’) is a typically self-deprecating, musically jaunty portrait of the titular tourist who has some unhealthy characteristics that Walker likely shares.

“He’s a happy little camper in Belize”, he sings with barely hidden antipathy.

Holler Country Music

Tried & True Music | 1998 ? videoThumbnail.image_asset.caption : ''}

17
Holler Country Music

ATCO | 1969

About Her Eyes

Walker hadn’t found his voice yet on this early (1969) folk pop ballad, but it’s an exquisite, fragile tune as the singer describes not just how beautiful a young lady is, but how her memory remains when she leaves the room. It might be unrequited love as the melody lingers like the woman’s vibe. Well worth searching out.

Holler Country Music

ATCO | 1969 ? videoThumbnail.image_asset.caption : ''}

16
Holler Country Music

Sony BMG | 2007

The Ballad of Jerry Jeff Walker

This heartfelt and earnest tribute to the Texas troubadour by Brooks and Dunn gets an extra dose of authenticity by Walker’s featured appearance.

They capture everything that’s cool about him too, musically and in the lyrics of “Talking outlawed, long hair loners and stoners”. Walker ought to have recorded his own version.

Holler Country Music

Sony BMG | 2007 ? videoThumbnail.image_asset.caption : ''}

15
Holler Country Music

Tried & True Music | 1990

Blue Mood

The 1991 low-key groove and easy listening vibe obscures some depressing lyrics about getting ripped off in the music business and confronting mortality in “the blue mood I’m in” that knocks the singer down to his knees.

The music is slicker than most Walker tunes but the words are some of his most personal and introspective.

Holler Country Music

Tried & True Music | 1990 ? videoThumbnail.image_asset.caption : ''}

14
Holler Country Music

Tried & True Music | 1998

Fred Neil Medley

Walker pays humble tribute to one of his major influences by combining ‘The Dolphins’ with ‘Everybody’s Talkin’’ in this supple 1988 medley, sung with warmth and an obvious appreciation of Fred Neil’s musical and lyrical simplicity. The tempo lopes along as the singer’s deep voice caresses these tunes that morph together effortlessly.

Holler Country Music

Tried & True Music | 1998 ? videoThumbnail.image_asset.caption : ''}

13
Holler Country Music

Tried & True Music | 2001

Texas On My Mind

Jerry Jeff covered this breezy tune, penned by his son Django (named after the great guitarist Django Reinheart).

The song had already topped the Texas music charts in a recording by Pat Green, but dad’s performance on 2006’s Gonzo Stew adds an extra dollop of fatherly sentimentality as the singer longs for a girl he foolishly left behind in Texas.

Holler Country Music

Tried & True Music | 2001 ? videoThumbnail.image_asset.caption : ''}

12
Holler Country Music

Tried & True Music | 1989

I Feel Like Hank Williams Tonight

This cover of a Chris Wall written track felt like it emerged from Walker’s pen as it became one of the breakout tunes from 1989’s Live From Gruene Hall.

The weeper describes how the singer’s wife called to say she is leaving him, and even though he loves Beethoven, Charlie Parker and Chuck Berry’s music, the sorrowful situation makes him play Hank’s records tonight. Profoundly felt and moving.

Holler Country Music

Tried & True Music | 1989 ? videoThumbnail.image_asset.caption : ''}

11
Holler Country Music

MCA | 1975

Jaded Lover

A deeper track written by Chuck Pyle from 1975’s terrific Ridin’ High finds Walker finally leaving a two-timing “angel whose wings just won’t unfold”.

He’s backed by kicking pedal steel and the tune is sung with the swagger and restlessness Walker exuded with such offhand charm, even in anger. He closes with “Goodbye you jaded lover / You undercover queen for a day.” Ouch.

Holler Country Music

MCA | 1975 ? videoThumbnail.image_asset.caption : ''}

10
Holler Country Music

MCA | 1973

Up Against The Wall, Red Neck Mother

Ray Wylie Hubbard’s classic has been recorded by many others (Bobby Bare also had a hit with it). But it became one of Walker’s signature tunes when he unleashed it on Viva Terlingua with plenty of hootin’ and hollerin’ from a well-oiled audience, singing along to “kickin’ hippies’ asses and raisin’ hell,” and seemingly meaning it.

Holler Country Music

MCA | 1973 ? videoThumbnail.image_asset.caption : ''}

9
Holler Country Music

Decca | 1972

L.A. Freeway

In 1972, Walker beat Guy Clark to recording his gotta-get-out-of-L.A. song by three years (it ended up on the latter’s 1975 debut).

Since then, most incorrectly assume it’s a Walker original. He certainly owns it in a performance replicating the relaxed, easygoing Austin attitude that made Walker’s music so much a reflection of that town’s overall vibe. 

Holler Country Music

Decca | 1972 ? videoThumbnail.image_asset.caption : ''}

8
Holler Country Music

MCA | 1973

Sangria Wine

Another track off the legendary Viva Terlingua has Walker going tropical, leaning towards Jimmy Buffett territory by replacing a margarita with the titular alcoholic libation.

It’s a frothy, fun romp as the singer and his Lost Gonzo Band go for attitude over slickness (gotta love his voice breaking at 3:50).

Holler Country Music

MCA | 1973 ? videoThumbnail.image_asset.caption : ''}

7
Holler Country Music

Decca | 1972

Hairy Ass Hillbillies

No one will accuse Walker of being PC, which is part of his appeal. But here, the hairy ass hillbilly from this 1972 party track is an affectionate term describing Walker and his friends (Billy Swan is name-checked) and isn’t meant to offend.

Extra credit for the mention of an electric dildo, not something you hear much in country music.

Holler Country Music

Decca | 1972 ? videoThumbnail.image_asset.caption : ''}

6
Holler Country Music

Ryko | 1994

What I Like About Texas

Gary P. Nunn’s love letter to the Lone Star State could be its official anthem. It gets an appropriately swaggering Jerry Jeff treatment in a frisky live version from 1994’s Viva Luckenbach!

The very vocal crowd provides extra hot sauce as he sings about burritos, dancing to ‘Cotton Eyed Joe’ and other attributes residents of the state typically love.

Holler Country Music

Ryko | 1994 ? videoThumbnail.image_asset.caption : ''}

5
Holler Country Music

MCA | 1991

Railroad Lady

This co-write with Jimmy Buffett (and apparently a bottle of Wild Turkey) made its debut appearance on Buffett’s 1973 album, but also became a sort of county standard when it was covered by Willie Nelson and of course Jerry Jeff.

The waltz-time gem tells of the semi-good looker who’s a little bit shady, “just trying to get home again” on various trains. Todd Snider also did a version on 2012’s Walker tribute album Time as We Know It.

Holler Country Music

MCA | 1991 ? videoThumbnail.image_asset.caption : ''}

4
Holler Country Music

Ryko | 1987

Layin' My Life On The Line

“Traveling is my way of life, and it gets so crazy sometimes” sings an appropriately weary sounding Walker as he ruminates about his profession.

More introspective and serious than most of his material, it’s a lovely, reflective melody closing with the poignant words “Your whole life's laid out in lines”, as in the lines of his songs. Sad and sweet.

Holler Country Music

Ryko | 1987 ? videoThumbnail.image_asset.caption : ''}

3
Holler Country Music

MCA | 1973

Desperados Waiting For The Train

Guy Clark’s standard has been recorded by numerous singer-songwriters who, like Walker, identify with the itinerant nature of travelers and the ravages of old age on once proud and vigorous lifelong drifters.

Walker’s unassuming yet touching vocals and sympathetic backing made his version one of the best though which, with competition from Steve Earle and The Highwaymen, is quite an accomplishment.

Holler Country Music

MCA | 1973 ? videoThumbnail.image_asset.caption : ''}

2
Holler Country Music

MCA | 1975

Pissin' In The Wind

A jazzy (check out the Dixieland clarinet) country sing-along from 1975 that perfectly captures Walker’s casual, offhand, loosey goosey attitude, as he tells stories about some of his friends, throws in a Dylan ‘Blowing in the Wind’ jibe and laments about sitting, grinning and telling his grandchildren about making the same mistakes he swore he’d never make again.

Holler Country Music

MCA | 1975 ? videoThumbnail.image_asset.caption : ''}

1
Holler Country Music

ATCO | 1968

Mr. Bojangles

What else could hold this spot? The early (mid-60s) pre-Texas tune remains Walker’s most popular, covered by dozens of others from Bob Dylan to Sammy Davis Jr. and Nina Simone.

It rose to number nine in the Billboard Hot 100 hit for the Nitty Gritty Dirt Band in 1971 (Walker’s version never made it past number 77).

The tune about Walker meeting an elderly black street performer in jail who “drinks a bit”, sung atop a sorrowful waltz-time beat, is in the folk tradition, with a rootsy melody that somewhat unexpectedly clicked with listeners, cementing Walker’s enduring legacy.

Holler Country Music

ATCO | 1968 ? videoThumbnail.image_asset.caption : ''}

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