Songfacts®:

• The Jimmy Webb recording "The Highwayman" is not to be confused with the Alfred Noyes poem or anything inspired by or based on it. Webb wrote his "Highwayman" himself, and it isn't really about a highwayman as such but reincarnation/mysticism, and has more in common with the Al Stewart song "One Stage Before" than with the Wishbone Ash track "Stand And Deliver."
  
  In a Songfacts interview with Jimmy Webb, he explained: "I remember that I wrote it in England, I was staying over there and I had a piano in my suite. I had dreamed about this highwayman being chased by these horses, like this kind of classical English scene, like they're folk heroes. Dick Turpin - I don't know whether Dick Turpin was a real man like Jesse James or whether he was like Paul Bunyan. But he's like the highwayman. There's a couple of famous English poems about highwaymen. They were definitely folk heroes of the Jesse James variety. And I had dreamed about this and it was a very vivid dream, came on to me very strong. I woke up kind of sweating and thinking, God, that was so real that was almost like a past life or something. And I went almost directly to the piano and started writing. I went from the highwaymen to the sailor to the dam builder. And a couple of hours went by and I was done, I was finished with it."
• Webb's recording of "The Highwayman" was released in 1977 on the Atlantic label, runs 3:51, and was produced by George Martin of The Beatles fame. Webb told Songfacts: "I called George Martin, who was in America. It was very weird, because I was in England calling George Martin who was in America, saying, 'Hey, George, I wonder if we could get this song on our album.' Because we were right at the end of our album. And he really liked it and wanted to do it."
• A single version was recorded by Glen Campbell the following year as "Highwayman" and released on the Capitol label in 1979; this one runs 3:05. Campbell also named the album Highwayman, and it was this album where things got tense between artist and label; Columbia wanted Campbell to cover the song "My Sharona," and he refused.
• The Highwaymen were the country supergroup of Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson. They took their name from this song, which they released on their debut album in 1985. Their version was a #1 Country hit and helped revive Jimmy Webb's career. Webb explained to Songfacts: "It was very successful for them. It was a #1 Country video. I won a Grammy that year for Best Country Song. We were pretty much ignored by CMA, because they didn't know what to do with that. It was like Waylon said one time, 'Which country?'
  
  They did a beautiful Highwaymen album cover where they had portraits of all four of them and then they had a highwayman with a desert, Monument Valley look to it, which was very cool. And then they had it painted on the side of their bus, 'The Highwaymen.' And they traveled that way for a long time. They had ten years or so and it was a big turnaround for me in my career to have a hit record in the '80s and something that was big on the Country charts and something that won another Grammy and everything. It was a big thing for me."
• It was Glen Campbell who introduced Cash, Jennings, Nelson and Kristofferson to this song. Says Webb: "When they were working on the very first Outlaw project, which they were all doing, Kris and Waylon and Willie were down there in Nashville working with Johnny Cash, because he wasn't feeling well, and he was obligated to do this album. And they said, 'Don't worry, we'll come down and we'll help you do it.' Which is a really nice thing for them to be doing. And I guess Glen stopped by to play some guitar, he was involved in it in some way that isn't 100% clear to me. But they told me that Glen played the song for them, and somehow or another they ended up recording it. It was a good thing for them, because there's four guys, there's four verses, each guy sort of plays a character, it's almost like a theatrical thing. It just worked out well for everybody."
• The Highwaymen version was released on the Columbia label and was produced by Chips Moman. Although judgments of this nature are largely subjective, most people would agree that Webb's original version is the best; he also recorded it as a duet with Paddy McAloon backed by an orchestra. >>>

  Suggestion credit:
  Alexander Baron - London, England
• Willie Nelson and Kris Kristofferson performed some of this song at the Grammy Awards in 2014. They were later joined on stage by Merle Haggard and Blake Shelton.