5 Defining Songs from ‘90s Outlaw Country Artists

Whatever the trend is in Nashville’s country music scene, that is what outlaw country is not. The genre first emerged in the 1970s, when artists like Willie Nelson, Waylon Jennings, and Kris Kristofferson grew tired of the influence of studio and label executives or institutions like the Grand Ole Opry over the kind of music artists were recording and performing. 

To some artists, Nashville had become a hit factory, churning out country songs that all followed the same formula and used the same instrumentation. Nelson and others wanted to break the mold. Initially, the term outlaw country described a subgenre of country music that was on one hand influenced by early honky-tonk music, and on the other by more modern genres like southern rock. The genre itself became so popular that the movement lost steam by the second half of the 1970s.

However, artists have continued to stretch the definition of country and to swim against Nashville’s mainstream. Here are five songs that all embodied the outlaw country spirit in the 1990s.

1. “Drown” by Son Volt (1995)

Written by Jay Farrar

After Jay Farrar and Jeff Tweedy went their separate ways and disbanded their previous project Uncle Tupelo, Farrar immediately formed the group Son Volt in 1994. Less than a year later, they released their debut album Trace. It did well, landing at No. 166 on the Billboard album charts. “Drown” opens with a simple but powerful distorted guitar riff. The bright tones and bends are country music’s bread and butter. The band expands on the genre with a much heavier hand and less familiar phrasing patterns in the lyrics. 

When in doubt
Move on
No need to sort it out
You’re with me now
Will be again
All other points in between
And I want to find the right side of you
If living right is easy
What goes wrong
You’re causing it to drown

2.“Where Will I Be” by Emmylou Harris (1995)

Written by Daniel Lanois

Emmylou Harris already had a long career in country music when she released her 18th studio album Wrecking Ball. It’s a fitting title since her new work surely wrecked some expectations audiences had when it came to a new release from Harris. The album won a Grammy in the category Best Contemporary Folk Album but there’s a lot more to hear than folk music. Harris enlisted different collaborators and drew from different musical influences way beyond the folk-country music world.

I walked to the river
And I walked to the rim
I walked through the teeth
Of the reaper’s grin
I walked to you
Rolled up in wire
To the other side of desire
Oh, where
Oh, where will I be
Oh, where
When that trumpet sounds

3. “The Saturday Option” by Lambchop (1998)

Written by Kurt Wagner

Lambchop started as a trio in 1986 but has since called more than a dozen musicians as band members. At the center of the group is vocalist and songwriter Kurt Wagner. Along with his bandmates, Wagner is on a mission to weave together country, soul, jazz, electronic music, and more. Merge Records, the band’s label, described Lambchop once as “Nashville’s most fucked-up country band.” 

The song “The Saturday Option” from the album What Another Man Spills opens with the sound of a pedal-steel guitar. The slow tempo would lend itself to a romantic country ballad, but alas, the opening line “Heaven is a disaster” reveals the composer had other plans. 

Yes, that was the best shot
Bleach is mixed with apricot
Regards are sent to authorities
Who maintain a set of priorities

4. “Let’s Kill Saturday Night” by Robbie Fulks (1998)

Written by Robbie Fulks

It’s outlaw country whenever you can imagine a mosh pit forming while the song is playing. “Let’s Kill Saturday Night” has a punk rock energy while still referencing country guitar vocabulary. The snare is ready to punch anyone in the face who disagrees with it. Fulks, who had already released a song cursing Nashville, is channeling rage once again on this track. The song is from his third album by the same name. 

I’ve got the Mustang loaded
I’ve got a wrong to right
I’ve got a little red bullet
Let’s kill Saturday night
Knock it out its misery
Nail that coffin tight
High living that’s history
Let’s kill Saturday night

5. “Can’t Let Go” by Lucinda Williams (1998)

Written by Randy Weeks

Lucinda Williams has been on the lineup of every single Outlaw Country Cruise since 2016 and that’s just one reason she fits this bill of outlaw country hitmakers. She had her big mainstream breakthrough in the 1990s with her album Car Wheels on a Gravel Road. It took Williams a long time to make the album and she worked with several producers, most notably Steve Earle in Nashville and Roy J. Bittan. Out came a mixture of fresh-sounding songs that won Williams a  Grammy for Best Contemporary Folk Album. One of the standout tunes is “Can’t Let Go”, which has a pulsating beat, a gritty slide guitar solo, and vocals with a lot of attitudes.

He won’t take me back
When I come around
Says he’s sorry then he pulls me out
I got a big chain around my neck
And I’m broken down like a train wreck
Well, it’s over, I know it
But I can’t let go

Photo by David Redfern/Redferns