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The Highwaymen was an American country music supergroup, composed of four of country music's biggest artists who pioneered the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Between 1985 and 1995, the group recorded three major label albums as The Highwaymen: two on Columbia Records and one for Liberty Records. Their Columbia works produced three chart singles, including the number one "Highwayman" in 1985.

Highwayman
Formed in 1985, the group did not have an official name when they released their first two albums on Columbia Records. The first album, Highwayman, was credited to "Nelson, Jennings, Cash, Kristofferson". The single "Highwayman", a Jimmy Webb composition, became a #1 country hit. Their cover of Guy Clark's "Desperados Waiting for a Train" reached the Top 20. The album was produced by Chips Moman.

Highwayman 2
In 1990, the four members reunited for a second effort, titled Highwayman 2, which reached #4 on the country album chart. The Lee Clayton-penned song "Silver Stallion" was the first single and made the country Top 40. The album was nominated for a Grammy for Best Country Vocal Collaboration. Highwayman 2 was produced, once again, by Moman. Six of the songs were written or co-written by members of the group.

The Road Goes on Forever
The group's final release (now listed as "Highwaymen") prior to Jennings's death in 2002 was 1995's Don Was-produced album The Road Goes on Forever, (a Robert Earl Keen cover), with the single, "It Is What It Is". A tenth-anniversary edition of The Road Goes on Forever appeared in 2005, with several bonus tracks added as well as, in some versions, a DVD containing the video for "It Is What It Is" and a documentary titled Live Forever – In the Studio with the Highwaymen.

Final years: Jennings and Cash’s health issues and deaths, breakup, aftermath, and occasional partial reunions
The band continued to tour into the late 1990s, before Jennings and Cash both started to decline in health, which prevented them from maintaining a full touring schedule. All four continued to perform as solo artists, with Jennings briefly joining another country supergroup, Old Dogs; Jennings died in 2002, and Cash died in 2003.

Nelson and Kristofferson collaborated on multiple occasions following the deaths of Jennings and Cash, but they were not credited as The Highwaymen for these occasions. For example, in November 2003, Nelson and Kristofferson reunited to perform "Big River", one of Cash's songs that he had re-recorded in 1985 with his Highwaymen bandmates, with George Jones at a Grand Ole Opry-sponsored memorial concert for Cash at the Ryman Auditorium in Nashville, Tennessee.

"Those tours and the records we made were a great time," recalled Kristofferson in 2010. "I just wish I was more aware of how lucky I was to share a stage with those people. I had no idea that two of them would be done so soon. Hell, I was up there and I had all my heroes with me. These are guys whose ashtrays I used to clean. I'm kinda amazed I wasn't more amazed.

In 2012, Kristofferson, Jamey Johnson, and Snoop Dogg collaborated with Nelson on the single "Roll Me Up and Smoke Me When I Die".

In 2016, Nelson and Kristofferson recorded a virtual collaboration of “One Too Many Mornings”, featuring archived vocals by Cash and Jennings recorded during the 1980s. This was released as a bonus track on the 2016 live album “Live: American Outlaws,” recorded at Nassau Coliseum in 1990.

Kristofferson died on September 28, 2024,leaving Nelson as the last living member of the Highwaymen.