After a night of drinking with Harry Nilsson, Jimmy Webb wrote the song “The Highwayman.” Released in 1977, the song came in a dream to Webb, the singer and songwriter behind Glen Campbell‘s “Wichita Lineman” “Galveston” and “By the Time I Get to Phoenix,” Art Garfunkel‘s 1973 hit “All I Know,” and more. “The Highwayman” followed the story of an outlaw, running from the law, which later inspired the formation of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson‘s outlaw supergroup The Highwaymen.
Throughout the Highwaymen’s decade-long run and three albums together, from the mostly covers-driven Highwaymen in 1985, to Highwaymen 2 (1990), which included six of the 10 tracks originals by Nelson, Jennings, Kristofferson, and Cash, and their final union, The Road Goes on Forever in 1995, all four highwaymen contributed songs pulled from their catalogs along with a few newly written tracks.
Highwaymen 2 featured Nelson’s “Two Stories Wide” and the closing “Texas,” while Cash penned “Songs That Make a Difference,” and Jennings contributed his “Angels Love Bad Men,” first recorded by Barbra Mandrell in 1987. Jennings’ “I Do Believe,” Nelson’s “The End of Understanding,” and Cash’s “Death and Hell,” co-written with son John Carter Cash, also slipped into the band’s final album.
Kristofferson also revisited three songs from his past on Highwaymen 2 and The Road Goes on Forever. Here’s a look behind the three songs Kristofferson wrote and rerecorded with his fellow outlaws on their final two albums.
Videos by American Songwriter
“Anthem ‘ 84”
Written by Kris Kristofferson
On his 1986 album Repossessed, featuring backing band the Borderlords, Kristofferson contemplates the state of America in 1984. At the time, Kristofferson was at a crossroads with his film career taking off in the early ’80s. He was also centered more on political activism, which is also peppered into Repossessed, including his criticisms of the then-administration under President Ronald Regan and its policies around El Salvador and the Contra rebels in Nicaragua, as well as some familial ties with “The Heart,” a tribute to his father Lars Henry Kristofferson (1905-1971)—and later covered by Highwaymen Jennings and Cash.
As a former Army captain, Kristofferson acknowledges the need to fight for freedom but questions the government sending troops out for self-interest on “Anthem ’84″—If you’re looking for a fighter who’ll defend you / And love you for your Freedom, I’m your man … But vision slowly faded like the wonder from your eyes / And you traded your compassion for your pride.
Kristofferson never released “Anthem ’84” as a single, but he did return to revisit it on the Highwaymen’s second album with a more electric, keyboard-driven version.
If you’re looking for a fighter who’ll defend you
And love you for your Freedom. I’m your man
And I ain’t gonna leave you for the crazy things you’re doing
But don’t ask me to lend a helping hand
You were such a pretty dream as I remember
You were young and strong and God was on your side
But vision slowly faded like the wonder from your eyes
And you traded your compassion for your pride
But I still believe in all that we believed in
And I pray to God that you will in the end
And you’ll see the golden chances that you’re wasting
And be the loving beauty that you can
“Living Legend”
Written by Kris Kristofferson
Along with Kristofferson’s anthem, the group also covered his 1978 song “Living Legend.” Originally released as on Kristofferson’s eighth album Easter Island, “Living Legend” is the penultimate track on the Highwaymen’s second album, Highwaymen 2 from 1990.
“Here’s an old song that could have been sung by an old soldier who rode with Chapata, or Che Guevara, or Jesus Christ—one of them revolutionaries,” said Kristofferson before performing “Living Legend” with the Highwaymen in 1990.
Was it bitter then with our backs against the wall?
Were we better men than we’d ever been before?
Say, if she came again today, would you still answer to the call?
Tell the truth, my friend, don’t it matter anymore?
We were simple men by her side when she was born
It was simple then like the freedom when you fall
And we were smaller then, you see, but soon we gathered like a storm
They don’t understand what that thunder meant at all
Was he crucified? Was he done in by the lawman?
Are you satisfied that he’ll never ride again?
Some people say he got away; they say he never died at all
If that story’s true, does it bother you, my friend?
“Here Comes That Rainbow Again”
Written by Kris Kristofferson
Though “Here Comes That Rainbow Again” originally appeared on Kristofferson’s 1982 collaborative album The Winning Hand with Willie Nelson, Dolly Parton, and Brenda Lee, he revisited it for the Highwaymen’s final album, The Road Goes On Forever. Before the Highwaymen took it on, Cash also covered “Here Comes the Rainbow Again” on his 70th album Rainbow in 1985.
The scene was a small roadside café
The waitress was sweepin’ the floor
Two truck drivers drinkin’ their coffee
And two okie kids by the door
“How much are them candies?” They asked her
“How much have you got?” She replied
“We’ve only a penny between us”
“Them’s two for a penny, ” she lied
And the daylight grew heavy with thunder
With the smell of the rain on the wind
Ain’t it just like a human?
Here comes that rainbow again
Photo: David Redfern/Redferns
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