"Highwayman" is a song written by American singer-songwriter Jimmy Webb, about a soul with incarnations in four different places in time and history: as a highwayman, a sailor, a dam builder on the Hoover Dam, and finally as an astronaut. Webb first recorded the song on his album El Mirage, released in May 1977. The following year, Glen Campbell recorded his version, which was released on his 1979 album Highwayman. In 1985, the song became the inspiration for the naming of the supergroup The Highwaymen, which featured Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson. Their first album, Highwayman, became a number one platinum-selling album, and their version of the song remained number one on the Hot Country Songs Billboard chart for twenty weeks. Their version earned Webb a Grammy Award for Best Country Song in 1985. The song has since been recorded by other artists. Webb himself included a different version on his 1996 album Ten Easy Pieces, a live version on his 2007 album Live and at Large, and a duet version with Mark Knopfler on 2010 album Just Across the River.
According to Jimmy Webb, he wrote the song in London while he was finishing up work on his album El Mirage, which was produced by George Martin. After a late-night round of "professional drinking" with his friend Harry Nilsson, Webb went to sleep and had "an incredibly vivid dream":[1]
I had an old brace of pistols in my belt and I was riding, hell-bent for leather, down these country roads, with sweat pouring off of my body. I was terrified because I was being pursued by police, who were on the verge of shooting me. It was very real. I sat up in bed, sweating through my pajamas. Without even thinking about it, I stumbled out of bed to the piano and started playing "Highwayman". Within a couple of hours, I had the first verse.[1]
Harry Nilsson is mentioned by Jimmy Webb. If anyone has Netflix, I highly recommend watching a documentary about HN - “Who Is Harry Nilsson (And Why Is Everybody Talkin' About Him)?” I thoroughly enjoyed it.