Introduction
Four Legends, One Timeless Journey: The Highwaymen Bring New Soul to “City of New Orleans”
When a song already has deep roots in American musical history, it takes something truly special to breathe new life into it. That’s exactly what happened when The Highwaymen – City of New Orleans (1990) brought their legendary talents together for a rendition that not only honored the original but expanded its emotional resonance. Originally written by Steve Goodman and made famous by Arlo Guthrie, “City of New Orleans” is a traveling ballad steeped in the bittersweet beauty of a country in motion. But in the hands—and voices—of Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson, the track becomes something far greater: a meditation on time, place, and the enduring power of the American spirit.
The Highwaymen – City of New Orleans (1990) is a standout not just because of its musical arrangement, but because of the unique charisma and character that each member brings to the performance. Johnny Cash delivers the opening lines with a steady, weathered gravitas that instantly grounds the listener. Willie Nelson’s signature phrasing brings a gentle wistfulness to the melody, while Kris Kristofferson and Waylon Jennings infuse the track with richness and grit. Together, their harmonies feel organic and unforced, a natural merging of distinct voices that reflect the diversity and unity of the American landscape they sing about.
What makes this rendition so special is the way it captures the soul of the train journey—not merely as a means of transportation, but as a symbol of life’s passage. From “riding on the City of New Orleans” to “passing trains that have no names,” the lyrics feel more poignant when sung by men who themselves are icons of a passing era. There’s a genuine reverence in their delivery, a sense of looking back with affection and forward with humility.
Whether you grew up with the original or are hearing this version for the first time, The Highwaymen – City of New Orleans (1990) offers a moving, masterful interpretation that resonates across generations. It’s not just a song about a train ride—it’s a reflection of who we are, where we’ve been, and the voices that help us remember it all.
Video
Lyrics
Ridin’ on the City of New Orleans
Illinois Central, Monday mornin’ rail
15 cars and 15 restless riders
Three conductors, 25 sacks of mail
All along the southbound odyssey the train pulls out of Kankakee
Rolls along past houses, farms and fields
Passin’ graves that have no name, freight yards full of old black men
And the graveyards of rusted automobiles
Good mornin’ America, how are you?
Don’t you know me? I’m your native son!
I’m the train they call the City of New Orleans
I’ll be gone 500 miles when the day is done
Dealin’ cards with the old men in the club car
Penny a point, ain’t no one keepin’ score
Pass the paper bag that holds the bottle
And feel the wheels grumblin’ neath the floor
And the sons of Pullman porters and the sons of engineers
Ride their fathers’ magic carpet made of steel
Mothers with their babes asleep, rockin’ to the gentle beat
And the rhythm of the rails is all they feel
Good mornin’ America, how are you?
Don’t you know me? I’m your native son!
I’m the train they call the City of New Orleans
I’ll be gone 500 miles when the day is done
Nighttime on the city of New Orleans
Changin’ cars in Memphis, Tennessee
Halfway home, we’ll be there by mornin’
Thru the Mississippi darkness rollin’ down to the sea
But the towns & people seem to fade into a bad dream
And the steel rail still ain’t heard the news
Conductor sings your songs again
The passengers will please refrain
This train has got the disappearing railroad blues
Good mornin’ America, how are you?
Don’t you know me? I’m your native son!
I’m the train they call the City of New Orleans
I’ll be gone 500 miles when the day is done
I’ll be gone 500 miles when the day is done
I’ll be gone 500 miles when the day is done