Watch Kris Kristofferson’s Legendary Nassau Coliseum Performance with The Highwaymen in 1990

The Highwaymen formed in 1985, the supergroup made up of Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. They were active until 1995, with one of their biggest hits being the song “Highwayman.” They released three albums in those 10 years—Highwayman, Highwayman 2, and The Road Goes On Forever.

Highwayman 2 was released in 1990, and the group recorded a concert at Nassau Coliseum in New York. They would go on to play a sold-out tour in support of the album—despite Johnny Cash’s broken jaw. In honor of Kris Kristofferson, who passed away on September 28 at the age of 88, here’s a look at the country supergroup performing their hit “Highwayman” from that 1990 Nassau concert.

Heartbroken over the recent passing of legendary country singer Kris Kristofferson at the age of 88.

Here is Kris with The Highwaymen performing "Highwayman" Live at Nassau Coliseum, 1990.

Rest In Peace legend 🙏 pic.twitter.com/BSX1Iasko2

— 🎸 Rock History 🎸 (@historyrock_) September 29, 2024

[RELATED: Country Icon Kris Kristofferson Dead at 88]

Watch Kris Kristofferson and The Highwaymen Perform to Sold Out Crowd in 1990

Willie Nelson opened the song to thunderous applause from the audience as soon as he uttered the first words, I was a highwayman / Along the coach roads I did ride. The four country legends were lined up on the stage, not one above the other, laughing together and looking like they were enjoying their own concert.

The crowd erupted in cheers once again when Kris Kristofferson took the next verse. I was a sailor / I was borne upon the tide, he sang in his mellow voice. Strumming his guitar, he looked out over the crowd and at his fellow Highwaymen as he performed.

While in the 90s there were rumors that The Highwaymen were having troubles—most notably claiming that egos were getting in the way, as well as Kristofferson’s penchant for sharing his political views on stage—allegedly those rumors were unfounded. In Willie Nelson’s 2015 autobiography My Life, he mentions this briefly.

“Rumours spread that Waylon, Johnny, Kris, and I were having ego problems and fighting like cats and dogs,” wrote Nelson. “The rumors were bulls–t. We saw it as one nonstop transcontinental party…I don’t mean that we didn’t get a little cranky from time to time…For the most part, though, it was smooth sailing.”

The Highwaymen continue to be a beloved supergroup for country music fans everywhere. There’s nothing like seeing famous friends getting together just for the sake of making music with each other.

Featured Image by Rob Verhorst/Redferns)