Bob Dylan

The Best Bob Dylan Country Songs

October 18, 2022 9:40 am GMT
Last Edited February 14, 2024 9:53 am GMT

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While Bob Dylan isn’t always thought of as curator of country music, he was one of the single most influential early instigators of rock’s crossover to country.

After recording his landmark Blonde on Blonde in Nashville, he gifted the world John Wesley Harding and Nashville Skyline, two hugely influential albums that resonate to this day.

Here is Holler's list of 15 of the best Bob Dylan country songs:

Columbia Records | 1975

Open the Door, Homer

Another seeming toss-off from the Basement Tapes, ‘Open the Door, Homer’ has a casual, uncomplicated sound of easy, breezy traditional Americana, albeit with a hint of humor and understated urgency.

The chemistry between Bob and the Band underscores the understated urgency and a decided lack of pretence and posturing.

Columbia Records | 1975

You're Going To Make Me Lonesome When You Go

Dylan eschews allegory in favor of emotion while begging his lover not to abandon him entirely. Like any Dylan song flush with emotional engagement, it inspired Dylan devotees to debate its true meaning.

Most believed it spoke to his wife Sara during their estrangement, but, as always, Dylan remains evasive about his actual intents.

Columbia Records | 1989

Man in the Long Black Coat

Both haunting and harrowing, this song moves slowly and deliberately as it traces a tale of a mysterious stranger who seduces a woman amid the ambiance and environs of Southern confines.

“Crickets are chirpin' the water is high / There’s a soft cotton dress on the line hangin' dry…”A homespun homily, it’s eerily effective.

Columbia Records | 1991

Mama, You Been On My Mind

A relative rarity released on the first volume of Dylan’s Bootleg Series, ‘Mama You Been on My Mind’ was supposedly inspired by Dylan’s break-up with his longtime girlfriend Suzy Rotolo.

Rarely had Dylan been so forthright in his feelings, and its jaunty melody and touch of twang underscored the sincerity of his sentiments.

Columbia Records | 1967

I'll Be Your Baby Tonight

John Wesley Harding represented a seismic shift in Dylan’s trajectory, an attempt to retrace the rootsy origins of essential American music.

This particular track reflected those downhome designs by way of a simple, straight-forward love song, backed by Nashville studio veterans Charlie McCoy on bass and Kenny Buttrey on drums.

Columbia Records | 1975

Buckets of Rain

Another of Dylan’s most compelling and committed love songs, this track, culled from what remains arguable Dylan’s best album of all time, Blood on the Tracks, offers an homage to the woman who’s given him “all the love” he can stand. Borne simply by acoustic guitar and bass, the sentiments stand on their own.

Columbia Records | 1969

Lay, Lady, Lay

No list of Dylan country classics would be complete without this carefully crooned entreaty. A top 10 hit, it nevertheless shocked his fans, given it signaled a new sound bereft of his trademark nasally nuances.

The predominant pedal steel guitar underscores both the change in tone and Dylan’s role as a suitor intent on seduction.

Columbia Records | 1975

Million Dollar Bash

Famously recorded with the Band as part of the legendary Basement Tapes sessions, ‘Million Dollar Bash’ reflects the carefree exuberance that accompanied the musicians’ desire to simply let go of commercial constraints.

Dylan plays the role of the observer, commenting on the characters he encounters at a boss bash and all their casual cool.

Columbia Records | 1975

You Ain't Goin' Nowhere

Although the lyrics may seem somewhat cryptic (“Genghis Khan and his brother, Don / Couldn’t keep on keepin' on”), that final resolve about flying down in an easy chair brings the country comforts to full throttle.

Famously recorded by the Byrds for their landmark Sweetheart of the Rodeo album, it ensured country credibility.

Legacy Records | 2019

Ring of Fire

A rare outtake from the Self Portrait sessions, this Johnny Cash cover demonstrated that Dylan’s early interest in country music is no fluke. His admiration for Cash was evident early on.

It’s one of two tracks that didn’t make the cut — the other being the Cash classic ‘Folsom Prison Blues’.

Columbia Records | 1969

I Threw It All Away

Regret and remorse frequently intrude on Dylan’s most sobering songs, and this bittersweet ballad provides a profound statement about sadness that’s second-guessed.

“I never knew what I had / Until I threw it all away.” For a man who titled his 1967 documentary Don’t Look Back, it marks a decided change in tack.

Columbia Records | 1969

To Be Alone With You

Another Nashville Skyline standout and supposedly influenced by Jerry Lee Lewis, ‘To Be Alone With You’ was the first song Dylan recorded for the album.

A simply stated love song, it’s both earnest and engaging, making no secret of Bob’s affection for his muse: “Everything is always right / When I'm alone with you”.

Columbia Records | 1969

Girl from the North Country

Recycled from Dylan’s sophomore album, The Freewheelin’ Bob Dylan, ‘Girl from the North Country’ qualifies as a song of true country calibre courtesy of Dylan’s somewhat off-kilter duet with friend and mentor Johnny Cash.

Originally derived from British folk tradition, this pinning and plaintive love song represents a true yearning lament.

Columbia Records | 1969

Country Pie

A jaunty diversion, ‘Country Pie’ was one of the more lighthearted offerings from Nashville Skyline, a genuine digression from the heady happenstance the once-rebellious Bob had purveyed prior.

Still, the bewildering wordplay remained the same: “Just like old Saxophone Joe / When he's got the hogshead up on his toe…” Huh?

Columbia Records | 1969

Tonight I'll Be Staying Here With You

“Throw my ticket out the window, throw my suitcase out there too…”

Few songs demonstrate such decided dedication to any object of romance. Sung with the considered croon that he briefly adapted for Nashville Skyline, Dylan plies one of his most direct love songs and leaves no doubt as to his care and commitment.

Listen and subscribe to Holler's the Best Bob Dylan Country Songs playlist below:

Written by Lee Zimmerman
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