The Highwayman
“What really suggested the song is a very vivid dream I had in London.. And it was the only one I ever had like that. And in essence it’s the first verse of the song. It was a wild pursuit of me by guys with…It was just terrifying and I woke up and I had sweat pouring off me. The last three verses are kind of suggested by the first. It is not meant to be a personal account of channeling or anything like that. It has, for me, a lot of symbolism. It’s about the kind of people who built this country up. The first verse is the rogue, the outlaw nation, the highwayman nation. The second verse is the seafaring nation; the trading and the growth of a nation, and its subsequent generations adding to that. And then the dam builder is a generation of construction and science and technology. And then the last verse is a spacefarer; he’s gonna fly to a starship. And so, it’s an American allegory. It’s Everyman, in a way.”Jimmy Webb (195)
“I was in London, finishing an album, ‘El Mirage’, with George Martin. My friend Harry Nilsson was there, and we were doing some professional drinking. He left my apartment one night, and I went to sleep and had an incredibly vivid dream where 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 some police, who were right 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. Nilsson hated that line in the first verse, “Along the coach roads I did ride.” He would say, “You mean, ‘Along the coach roads you rode?’ (laughs) In that particular case, I felt it was justified because it was kind of an antique way of speaking. I didn’t know where the song was going. Then I realized that this guy doesn’t really die in the first verse. He’s reincarnated. I started thinking, “Where does this soul go?” The verses started to evolve. He becomes a sailor, then a dambuilder. Then the best idea for me was switching the tense into the future and say, “I’ll fly a starship across the universe divide until I reach the other side”.”Jimmy Webb (905)
Wooden Planes
“When I think about my childhood, I remember it through pictures, images in my head. I was 6 years old in that particular place, where “Wooden Planes” is, where I remember that. I just have this picture of my brother and I. My father made these airplanes by hand. He made them out of orange crates. And he whittled propellors for them. And when you held them up, the wind would turn them. They were fabulous. They were magical.”Jimmy Webb (196)
Met Her On A Plane
“They’ve just done a study that determines unequivocally that men are more emotional and vulnerable on aircraft than they are at any other time. They’re on a plane and they open up, so I think ‘Met Her On a Plane’ is about that kind of euphoria. It’s like saying, “I’d forgotten how vulnerable and breakable I was”.”Jimmy Webb (906)
Land’s End (The Album)
“It was very difficult, because she was married. I was bored with flirtations and one-nighters and all of the above, and I wanted a battleship of a love affair. And she walked into my dressing room after I played the Albert Hall and said, “I really enjoyed your music”. It was like being hit by a lightning bolt, and though I realized a moment later that I had met her before, that she was married, that it was hopeless or at least fraught with the perils of Odysseus, I plunged right into it. And it changed the course of my life and continues to do so to this day even though she committed suicide. It was a tragic thing from beginning to end, there was not a socially redeeming moment of it that I can put my finger on. It certainly diverted the course of my life the way some great natural disaster will change the course of a river. I loved her for many, many, many, many, many, many, many years, even after I was married. Human beings can become involved in emotional attachments that are too overpowering and too debilitating, and I began a rather rigorous campaign to kill myself, except I wanted to do it in a spectacular way – no sleeping pills for me, thank you. But I sort of grew tired of that, and once I was over 30 I needed another plan. Part of that plan was learning to live with the fact that she had affected me dramatically, that she was still in the world, that occasionally we would see each other and speak, but that I would no longer allow it to be life-threatening. So that’s really what Land’s End was about. It says love is a glass of wine balanced on the side-rail of a ship. I was always very fond of English girls, but looking back on it, I realize this was a person that had problems. I’d idealized her, but she had some very serious problems that I wasn’t prepared to recognize. 23 or 24 is much too young to be that serious about anybody or any thing. It makes great songs and spectacular death scenes, but it’s too high-octane.”Jimmy Webb (906)

High Rent Ghetto
“‘High Rent Ghetto’ was just a picture of life in the music business as it really is for most people – not for those ten people that are super-super-rich, but for people who make a living at it, that great unwashed crew who sort of made it but didn’t quite make it. They still have hopes and they still have to put their children through school.”Jimmy Webb (906)

Class Clown
“When I speak of “I met him without knowing him the other day and offered him my sacrifice and sent him on his way” is where the speaker has met an old classmate on the street and has discovered to his shock that this guy is now a homeless person. That is true. That actually happened to me, and he was the class clown, the funniest guy. The song begins, “he was the funniest kid in the class”. Now, that was true, and we all know that kid, so I am reaching out saying, “You know who I mean”. But you get to the end and you find yourself face to face with the funniest kid who is a homeless man. The shock of that is very real.”Jimmy Webb (907)

Time Flies
“In ‘Time Flies’… well, I’m 58 and am beginning to feel my mortality and all of these fantastic renegades that I cut my teeth on as a young musician listening to – the likes of Johnny Cash and Waylon Jennings, and Hank Williams and Woody Guthrie. And guys from my generation who were also renegades: Harry Nilsson who was my best friend – a wonderfully insane human being – and Richard Harris who recorded ‘MacArthur Park’ – was also delightfully out of his mind. David Hemmings too, a whole list of actors and musicians – many musicians, George Harrison – who are now passing on. There is no delicate way to put it.”Jimmy Webb (907)