Best Jessi Colter Songs: 20 Country Gems (2024)

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The “First Lady of Outlaw Country” is a title that can make it seem like Jessi Colter married into her esteemed position among the 70s rebels who turned Nashville upside down. But Colter had been making country music for nearly a decade when she met Waylon Jennings, writing hit songs under her first married name, Mirriam Eddy, and touring alongside her first husband Duane Eddy. The Arizona native did have a bit of an easier road to a record contract once Waylon was vouching for her, but her biggest hits were entirely her own: songs she composed, played piano on, and sang.

Within that often-overshadowed catalog are a slew of gems, songs that have long been given a perfunctory glance by people fixated on the work of Willie and Waylon and the boys. Waylon, however, was a steadfast creative partner to Colter, as evidenced by their many duets over the years and the fact that he co-produced most of her work. “Jessi is one of the most talented people I’ve ever known,” Jennings wrote in the liner notes of her debut album. “She is original in everything she does.”

Below are 20 of Colter’s best songs, ranging from the weepiest ballads to the sassiest boot-stompers and everything in between.

Listen to the best Jessi Colter songs now.

Roll On (1978)

On this J.J. Cale tune, Colter digs back into her country-soul roots (there’s even a horn section!) for a rowdy, party-ready result. It was on an album that was, unusually for Colter, all covers – likely compelled in part by record executives trying to recreate the outsized success of “I’m Not Lisa.” This good-timing tune helps show the wide range of both Colter’s music and the genre as a whole during the late ’70s.

You Hung The Moon (Didn’t You Waylon) (1976)

This love song Colter penned as one half of outlaw country’s biggest power couple was actually released as a single, albeit an unsuccessful one. It is endearingly earnest from Colter, and also reflects the (platonic) sentiment of so many country music fans who only wish they had the opportunity to be as effusive on record. Like most of Colter’s records, this one was co-produced by Jennings and featured him on guitar and background vocals.

Out Of The Rain (2006)

Colter’s first release following Jennings’ passing in 2002, this song was originally recorded in the ’80s and features Jennings as well as their son Shooter. By the time it was put on an album, it had been 22 years since Colter’s last country LP. Out of the Ashes was produced by Don Was, and on “Rain” he drew out Colter’s ongoing interest in gospel music and sounds for the ensemble recording.

That’s the Chance I’ll Have To Take (1970)

Here, Colter’s Nashville bona fides are made clear. “If I am wrong in what I do, that’s just a chance I’ll have to take,” she sings with sass worthy of Dolly or Loretta, against a Chet Atkins-crafted musical backdrop. If it’s not her most unique performance, it’s certainly a persuasive one – especially to anyone who might have thought these outlaws didn’t have what it took to hack it playing straight country.

Here I Am (1976)

A clear descendant of “I’m Not Lisa,” this original composition makes Colter’s evocative singing the centerpiece, as she pleads with an uncaring lover with an almost hymn-like solemnity. There is a note of Carole King in the song’s confessional tone, relating more to the adult pop of the late ’60s and early ’70s than the era’s country music.

Who Walks Thru Your Memory (Billy Jo) (1975)

This song finds Colter at her most traditionally country, lamenting lost love over a steady shuffle with more than a slight quiver in her voice as she serenades Billy Jo. Like all the songs on her breakout album, it was an original composition by Colter – complete with a fresh image, that of a past love walking through someone’s memory, to explain a familiar topic.

Hold Back The Tears (1978)

The singer-songwriter sounded natural as could be on this Neil Young song, which he had released the year prior with Linda Ronstadt singing backup. Colter makes it her own here, drawing out the twang to great effect and amplifying the song’s message of cautious hope. The album was a commercial failure, but its range of covers showed the singer’s versatility.

Suspicious Minds (1970)

Colter and Jennings chose to reprise this Elvis hit when it was still brand new – and reached the country charts twice with it, both upon its initial release as a non-album single and when it was included on the Wanted! The Outlaws compilation. It works perfectly as a duet, and as a showcase for the pair’s chemistry in and out of the studio. The country elements are amped up, including a full-on shuffle section, but the original Memphis-made groove still comes through as well.

It’s Morning (And I Still Love You) (1975)

Compelled to try to follow up the two crossover hits from her Capitol debut album, Colter offered the lilting, upbeat song that gave a one night stand a happy ending. Like her first two hits, it’s an original composition that also features Colter’s piano playing; unlike them, it only peaked at No. 11 on Billboard’s country chart. More hippie-ish and searching than her previous releases, the wailing pedal steel is pushed to the back in favor of folksy arpeggiated guitar.

Ain’t No Way (1976)

A rollicking tune with Jennings audible on the background vocals, “Way” is so anthemic you’d think it would have been covered numerous times – or at least released as a single. Instead, it was left a Diamond In The Rough, to use the album title’s chosen metaphor, relegated to album cut status despite the fact that Colter and Jennings are giving it their all.

That’s The Way A Cowboy Rocks and Rolls (1978)

The title track from Colter’s fifth studio album comes with a metaphor perfect for the country-rock sounds associated with the outlaws: a cowboy who rocks and rolls…away. It’s a pretty, relatively unadorned song, save Colter’s always charming piano playing and mellow backing vocals from Jennings. “Life is just one big old rodeo,” she sings, putting a reflective spin on the Western fervor that accompanied the outlaws’ fame.

You Ain’t Never Been Loved (Like I’m Gonna Love You) (1975)

The A-side to “What Happened To Blue Eyes,” this sexy, stripped-down single narrowly missed becoming another major hit for the singer-songwriter during her most successful period. With an almost Bobbie Gentry-esque bluesiness, Colter makes an assertive, torrid promise that sounds risqué even in the context of the era’s bedroom country trend. It’s a welcome anomaly in her catalog, music that is Southern more than it is strictly country.

You Mean To Say (1971)

A one-off single that was eventually rereleased on Wanted! The Outlaws, “Say” is another classic Colter composition – all engaging melody and evocative singing with a subtle, off-center twist on conventional country songwriting. This one is all outlaw, moody and conversational at once, resisting polish and pop. It never became a hit, but its place on Wanted!, the first platinum album in country music history ensured that it would always be remembered.

Maybe You Should’ve Been Listening (1978)

Colter was one of a number of country singers who tried to earn a hit with this Buzz Rabin composition, but her timeless, sensitive take is certainly standalone. Delivered with plenty of pathos and pedal steel, her performance is all Nashville and yet palpably sad; her warble cuts through the skill of the house band, right to the quick.

I Ain’t The One (1969)

Colter’s first recorded duet with Jennings was made and released the year they met and married. Though it failed to chart, its bright energy and easy country-soul sound showed that the pair had something special together – and that neither sounded quite like anything else Nashville had on offer at that moment. Capable of rich, gospel-inflected power and quivering balladry, Colter’s voice was a little more sultry than those of many of her Nashville peers – a quality that’s on display in this saucy back-and-forth.

I Thought I Heard You Calling My Name (1976)

A classic-sounding country tune about the ghost of lost love, this was Colter’s last single to reach the top 40 of the country charts. It’s a compelling showcase of her vocal range and her emphatic piano playing, though, an example of her skill as an interpreter who proved women could channel the rough-around-the-edges outlaw sound just as well as the men. It has the intimate sound of an after-hours roadhouse in place of any studio gloss.

Storms Never Last (1975/1981)

Another country classic penned by Colter that required several releases to get traction, “Storms” is both deeply romantic and uncharacteristically optimistic for the often melancholy singer. A 1978 Dr. Hook take on the Colter album cut helped turn the song into a standard, as did Colter’s eventual duet with Jennings of it for their 1981 joint album Leather and Lace. That rendition finally cracked the country charts, reaching No. 17 on the country charts.

I’m Not Lisa (1975)

Jessi Colter was already a veteran of the music industry by the time she released her first charting single, which also became the most successful one of her career. The plaintive ballad, which was written, sung and centered piano played by Colter herself, reached No. 4 on Billboard’s Hot 100 chart while topping the country charts. Though Colter would later become associated with the burgeoning outlaw country movement, “Lisa” is much closer to the pop stylings of the period in spite of its crooning pedal steel and the fact that it was co-produced by Colter’s husband Waylon Jennings. With a distinctive take on a classic country topic (a person who can’t get over their ex), “Lisa” became one of Colter’s signature tunes – not, as some would have it, proof that she’s a one-hit wonder.

Why You Been Gone So Long (1970)

Colter didn’t originate this song – Johnny Darrell scored a minor hit with the MIckey Newbury tune in 1969 – but her deeply groovy version has long since been definitive. A country-soul classic, this track transforms the original from standard issue Music Row fodder into something of a piece with the era’s fearless genre fusion. Her voice is clear and raw in what was, retroactively, something of an opening salvo for her outside-the-lines musical mission.

What’s Happened To Blue Eyes/ I’m Looking For Blue Eyes (1975/1976)

Colter’s gift for melody is rarely better showcased than it is here, on a timeless composition that has become a country classic. “Blue Eyes” is another pathos-laden ballad originally meant to follow up the singer-songwriter’s breakout hit “I’m Not Lisa” – this time, though, Colter backed her unpretentious, church-bred singing and piano with a decidedly two-step ready country shuffle. The first lady of the outlaws cemented her place when she re-recorded this track for the Wanted! The Outlaws compilation, stripping away any pop trappings in favor of a minimalist sound that centers her potent voice.

Listen to the best Jessi Colter songs now.