Introduction
A Journey Through Time and Melody: Revisiting The Highwaymen – City of New Orleans (Live 1990)
When four legends come together on one stage, something unforgettable is bound to happen. That’s exactly what took place in The Highwaymen – City of New Orleans (Live 1990), a stirring performance that brought the combined gravitas of Johnny Cash, Waylon Jennings, Kris Kristofferson, and Willie Nelson to a song already steeped in American cultural lore. Their rendition is more than just a live cover—it’s a reflection on history, movement, and the soulful heart of a country always on the move.
Originally penned by Steve Goodman and made widely popular by Arlo Guthrie and later Willie Nelson himself, “City of New Orleans” tells the story of a train and, more profoundly, the American spirit it carries. It’s a song about passage—of time, geography, and memory. When The Highwaymen performed it live in 1990, they did more than harmonize voices; they brought together decades of musical experience and personal journey, each man adding his own lived-in wisdom to the lyrics.
The charm of this live performance lies in its authenticity. It doesn’t try to dazzle with elaborate production or technical perfection. Instead, it’s grounded in what these four men do best: telling stories that matter, that linger in the heart long after the final chord. The Highwaymen – City of New Orleans (Live 1990) is marked by a palpable camaraderie on stage, the kind only longtime friends and musical compatriots can share. The audience doesn’t just hear the music; they feel the miles behind it.
Each voice in the quartet contributes something distinct. Johnny Cash brings gravity, Waylon Jennings a rugged edge, Kris Kristofferson a poetic soul, and Willie Nelson a melodic warmth. Together, they transform this train ride into a meditation on what it means to belong to a land as vast, complicated, and beautiful as America.
Whether you’ve been riding the rails of this country in person or only in spirit, listening to The Highwaymen – City of New Orleans (Live 1990) is like sitting by a train window, watching the past and present roll by. It’s a performance that reminds us that music—like travel—is not just about where you’re going, but about what you carry with you.
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