3 Songs Willie Nelson Contributed to The Highwaymen During the Supergroup’s 10-Year Span

On their eponymous1985 debut, The Highwaymen delivered an album of rousing covers from the John Prine and Steve Goodman-penned “The Twentieth Century Is Almost Over,” Woody Guthrie‘s “Deportee (Plane Wreck at Los Gatos),” Bob Seger’s “Against the Wind,” and Guy Clark’s 1973 hit ‘Desperados Waiting for a Train,” and more, along with two tracks written by Highwayman Johnny Cash.

By their second offering, The Highwaymen 2, six of the 10 tracks were originals by all four band members, including Cash, Kris Kristofferson, Willie Nelson, and Waylon Jennings, and on through the group’s third and final assembling, The Road Goes On Forever, in 1995.

Throughout their 10-year run, Nelson contributed original songs he wrote specifically for The Highwaymen, along with one he revisited from earlier in his career in the late ’60s. Here’s a look at Nelson’s three Highwaymen contributions.

[The Highwaymen Track Waylon Jennings Called “The Best Song I’d Ever Written”]

1. “Two Stories Wide” (1990)

Written by Willie Nelson

The supergroup’s second release The Highwaymen 2 from 1990 peaked at No. 4 on the Country chart, where it also spent 40 weeks. Of the 10 tracks, six were penned by Nelson, Kristofferson, Cash, and Jennings. Nelson wrote two, the closing “Texas” and the second track “Two Stories Wide,” drilling in the message of living in the moment because, as Nelson croons, Life’s too long to worry.

Come out of the darkness
Don’t hide in the night
Come out in the sunshine
And we’ll be alright

Life’s too long to worry
And it’s too short to cry
And it’s too deep to measure
And it’s too stories wide

There’s your side and my side
Which side do you need?
Both sides make you lonely
And make your heart bleed

2. “Texas” (1990)

Written by Willie Nelson

Nelson’s ode to his home state is an appropriate close to the supergroup’s second album. “Texas” is a simple tribute to the state, a sing-a-along about the place where Nelson says he belongs, where his spirit can be free, and how he longs to be back there.

Listen to my song
And if you wanna sing along
It’s about where I belong
Texas

Sometimes far into the night
And until the morning light
I pray with all my might
To be in Texas

It’s where I wanna be
It’s the only place for me
Where my spirit can be free
Texas

3. “The End of Understanding” (1995)

Written by Willie Nelson

By the end of The Highwaymen’s run, Nelson contributed one last song on their third and final album, The Road Goes on Forever, with a rerecording of his 1967 release “The End Of Understanding.” The 2005 reissue of The Road Goes on Forever, also features a rerecording of Nelson’s 1974 song “Pick Up the Tempo,” originally recorded on his collaborative album with Jennings, This Time.

Each time you hurt me, you say you’re sorry
I try to understand, and say: “OK”
But there must be an end to understanding
And the end of mine can’t be too far away

I try to understand that you’re “only human”
And “we all make mistakes” every day
But there must be an end to understanding
And I know that I just can’t go on this way

Don’t you know that love and understanding go together
Ask too much of one and both will die
And there must be an end to understanding
And I know, someday, I’ll reach the end of mine

Photo: David Redfern/Redferns