On This Day: Waylon Jennings, Johnny Cash, Kris Kristofferson, and Willie Nelson Record ‘Highwayman’

by Jonathan Howard
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37 years ago today four of country music’s greatest got together to record Highwayman.

Waylon Jennings, Johnny Cash, Kris Kristofferson, and Willie Nelson recorded the hit single back in 1984. They would then form the group The Highwaymen. For the next decade or so after they performed as the famous quartet. Nothing has been done like it before or since.

These four legends weren’t the first to record the song. It was written by Jimmy Webb and was on his 1977 album, El Mirage. Following that recording, Glen Campbell tackled the song in 1979. In fact, if it hadn’t been for Campbell the most famous version of the song would have never happened.

After some nudging, the four men would meet up in Switzerland for a TV special. It was all the way over in Europe where Cash and the rest decided to work on something together. Thank goodness they did. So, why don’t we check out the classic song with this 1990 performance from Nassau Coliseum?

When that guitar starts, it sends a chill down your spine just about every time. The almost ghostly lyrics about life’s lived in the past instantly grabbed country music fans’ interest. Four men lost to time who will, “Always be around.” Whether they are traveling the coach roads of America’s past or flying a starship sometime in the future.

Hitting the Top of the Charts

While Highwayman would have been a great song just on its own, of course, the group didn’t stop there. They recorded three albums in total as a quartet. That first single everyone knows and loves hit No. 1 on the charts. Then they would go on to release more singles.

The first album had a lot of success. It topped the country charts and even cracked the top-100 of the US charts. However, they would have more mainstream success with the second album. Highwayman 2 didn’t top the country charts. The sophomore album for the supergroup topped out at No. 4 for the genre. However, it went to 79 on the US charts against all genres.

Celebrating Highwayman and Keeping the Memory Alive

Since the group formed, only half of the members are still with us. Jennings and Cash passed away in 2002 and 2003 respectively. Willie and Kristofferson played at the 2014 Grammy Awards in a medley. Nelson is still going strong and released a family album this year.

However, perhaps no one else is doing more to honor the Highwaymen than the Highwomen. The all-women supergroup features Brandi Carlile, Maren Morris, Amanda Shires, and Natalie Hemby. Together they modified the 1984 classic.

So, if you can, put Highwayman on repeat and maybe even throw in the Highwomen. You won’t regret having these great voices playing throughout your day, that’s for sure.

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