HomeEntertainmentMusicOn This Day: The Highwaymen Release ‘The Road Goes on Forever’ in 1995

On This Day: The Highwaymen Release ‘The Road Goes on Forever’ in 1995

by Katie Maloney
(Photo by Jack Vartoogian/Getty Images)

Twenty-six years ago country supergroup, The Highwaymen covered the hit song “The Road Goes on Forever.” But what’s the story behind the song?

From 1985-1995 outlaw country artists Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson joined forces to create the music supergroup, The Highwaymen. During their time together, The Highwaymen released three major albums and three chart singles. Towards the end of their time together, the group released a cover of the hit song “The Road Goes on Forever.”

The song is about two lovers racing against the world and sticking to their troublesome ways until the end. During the song, The Highwaymen sing, “The stars were high above them and the moon was in the east. The sun was settin’ on them when they reached Miami Beach. They got a hotel by the water and a quart of Bombay gin. The road goes on forever and the party never ends.”


What The Story Behind The Highwaymen’s Song?

“The Road Goes on Forever” was written and originally recorded by Robert Earl Keen. Unlike many songs and albums, the song wasn’t a long-time in the making. In fact, Keen wrote the song in just a few days. What he didn’t know at the time was that countless artists would cover the song, including the famous supergroup The Highwaymen. During an interview in 2009, Keen shared how his biggest hit song came to be. Keen explained that he was in Nashville working on his third album, West Textures, in 1988. He was set to work with Jim Rooney, the same producer that worked with Townes Van Zandt and Nanci Griffith. However, just a few days before the completion of the album, Rooney put a hold on the record.

“We were set to do this record on Monday … two days recording, two days mixing … ’cause that’s all the budget would allow,’ said Keen. “We’re there Friday [previewing songs for Rooney], and he says ‘I don’t think we really have a song to hang our hat on here.'”

Rooney suggested that they postpone the album. But Keen was not in the financial position to do that.

“I was living on nickels and dimes at the time,” said Keen. “So, I was like, ‘I can’t do that … I can’t even afford to come back up here.'”

Robert Earl Keen Saved His Career With ‘The Road Goes On Forever’

So, Keen came up with an idea. He asked for just a couple of days to finish a song he had started writing a few months earlier. Rooney agreed and Keen got to work. Can you guess which song it was? If you guessed “The Road Goes on Forever,” you’re right! Keen returned to the studio and played the song for Rooney.

“It’s always embarrassing trying to pour your heart out to somebody to get their attention,” said Keen. “I played about three verses of the song, and he goes, ‘Oh, that’s it. We’ve got it.’ And I went, ‘Really?'”

Decades after its release, “The Road Goes on Forever” is still Keen’s most requested song. The Highwaymen helped increase its popularity, even more, when they released their cover in 1995.