With classics like “By the Time I Get to Phoenix,” “Galveston,” “MacArthur Park,” and “Wichita Lineman” to his credit, Jimmy Webb is a member of both the Songwriters Hall of Fame and the Nashville Songwriters Hall of Fame—and one of the few composers whose work ranks with Willie’s. On this week’s episode of One By Willie, Webb talks about another of his iconic compositions, “Highwayman.”

(Read a transcript of this episode below.)

Willie, of course, recorded it in 1985 with his buddies Johnny Cash, Waylon Jennings, and Kris Kristofferson, and it went on to be one of the biggest hits of each of their careers, winning a Grammy for best country song, as well as providing a name for country music’s first supergroup.

Written by Webb in the mid-seventies, “Highwayman” was one of those songs that had been bouncing around Nashville for almost ten years before it finally landed with the artists who would make it immortal. In this episode, Webb explains how he wrote the song, what it means, and the long path it took to get to Willie and the boys. He also comes up with a great idea for Willie’s next album.

We’ve created an Apple Music playlist for this series that we’ll add to with each episode we publish. And if you like the show, please subscribe and drop us a rating on Apple Podcasts or wherever you get your podcasts.

One by Willie is produced and engineered by Brian Standefer, with production by Patrick Michels. The show is produced by Megan Creydt. Graphic design is by Emily Kimbro and Victoria Millner.


John Spong (voiceover): Hey there, I’m John Spong with Texas Monthly magazine, and this is One By Willie, a podcast in which I talk each week to one notable Willie Nelson fan about one Willie song that they really love. This show is brought to you by White Claw Hard Seltzer.

This week, we talk with one of the greatest American composers who ever lived, Jimmy Webb. He’s the genius behind such monster hits as Glen Campbell’s “By the Time I Get to Phoenix,” “Wichita Lineman,” and “Galveston.” He also wrote, “Up, Up and Away,” “MacArthur Park,” and the song he’s going to discuss with us, “Highwayman.” That song, of course, gave its name to country music’s first supergroup, which consisted of Willie, Waylon, Kris Kristofferson, and Johnny Cash, and it went on to win the 1985 Grammy for Country Song of the Year. Jimmy’s going to tell us how he wrote it, how it wound up in the hands of those dudes, how Glen Campbell worked with producer Chips Moman to teach them the chords, and then he’ll come up with a great idea for Willie’s next record. It’s a particularly special episode of One By Willie, and I think you’re gonna dig it. So let’s do it.

[Willie Nelson singing “Highwayman”]

John Spong: Typically I start by asking, “What’s so great about song X?” And given that you wrote “Highwayman,” this seems like a goofier question than usual. And so, rather than that, I want to start, I think, by saying—well, let’s stipulate that “Highwayman” is a great song; I feel confident that I can get away with that—and go into how you wrote it, and what’s it about. Tell me about “Highwayman.”

Jimmy Webb: Well, as a matter of historical background, I was doing an album with George Martin, the great George Martin, called El Mirage. And I thought the album was finished, but I went over to London and hung out with my buddy Harry Nilsson for a while. And after a particularly raucous night together, we sort of stumbled to our respective hotel rooms. I went to sleep, and woke up in the middle of the night in a cold sweat, because I had dreamed this scenario where I was a highwayman. And it was . . . for lack of a better description, I think they call those the “night terrors.” And as far as I know, that’s the only time it ever happened to me. I had a piano in the room, I mean, ten feet away from the bed. And to date it exactly, it was when “Don’t Cry For Me Argentina” was a hit. And I rolled outta bed, and got on the piano bench, and wrote the first verse of “Highwayman.” And then I started putting the rest of it together over the next couple of days. 

As soon as I got back to L.A., the first person I played it for was Glen Campbell. And Glen went crazy for it. And he took it over to Capitol Records, because they were looking for new material for him. And he played it for them, and there was a crew of thirtysomethings in there who hadn’t been there for the whole twelve years, you know, $12 billion dollars worth of records. And they said, “Well, yeah, it’s nice. It’s good. It’s a Jimmy Webb song; it’s good.” They said, “But here’s what we want you to do,” and they put on a copy of “My Sharona.” And “My Sharona” was a great record; I want you to know that. I actually thought it had a pocket that was really kind of unbeatable, and I dug it as a rock and roll record. But Glen didn’t like it, and he walked out of Capitol and never went back. After twelve years, that was the parting of the ways. He went off and made his own version of “Highwayman.”

And I guess I should say at this point, that “Highwayman” is kind of a song with a spiritual bent. It’s not per se about reincarnation; it opens the door to the fact that maybe we do come back, but it also represents the kind of unquenchable spirit of man, of each man, and how that goes on.

John Spong: And the plot—the narrator is the same soul in each verse, but it’s a different person in each verse. And so, highwayman, sailor, dam builder, astronaut. It’s actually in the future beyond astronauts, so that’s probably not the word they would have used for that character. But was reincarnation, or souls moving and evolving, something that was on your mind? How did you . . .

Jimmy Webb: Well, I was thinking about that. And particularly, I wanted this character, this character in this song to be like a timeless character. He has no control over where he ends up, really. He starts out as a highwayman and ends up flying a starship. So in that sense, it’s also a description of the lack of control that any of us have over our destiny, really. So that’s pretty much spelled out in the song, is he’s in the pinball machine of the universe, and he’s banging around from one experience to the next. 

John Spong: Well, it’s interesting because with “Highwayman,” at first blush, those thirtysomethings at Capitol maybe thought it was a little weird or something. They couldn’t have had an objection to the melody. But if they thought that the concept or something was a little out there, Willie’s a little out there. And I’ve even read that he started believing in reincarnation as a little kid. And, like, he’s growing up during the Depression in Abbott, and a buddy of his, when he’s a little boy, another little boy who was a wild kid in Willie’s description in his autobiography, he said that kid died. And Willie thought to himself as a little kid, “He’s not going to get into heaven? He’s going to have to go to hell, because he didn’t live long enough to fix some of this stuff? I have a feeling he’s going to come back somewhere and correct those things later.” And that became something, a belief that really mattered to Willie going forward. So of course he wanted to do this song.

Jimmy Webb: Well, I think that . . . I believe in second chances myself. And people struggle a lot to try to make sense of life, and the most sense that it makes, to me—and I’m seventy-five now; I know I only look thirty, but I’m seventy-five—and life seems to me to be a learning experience. Because nobody gets it right the first time, that’s for sure.

[Willie Nelson singing “Highwayman”]

John Spong: I read somewhere that when you played it for Harry Nilsson the next morning, or whenever you did that first verse, he said he objected to the language, to the lyrics.

Jimmy Webb: Oh, let’s see. Oh yeah: “I was a highwayman / Along the coach roads I did ride.” He said, “You should never do that.” He said, “You should never say, ‘I did ride.’ ” He says, “That’s the way people used to talk, and people don’t talk that way anymore, so you really can’t do that.” Mind you, he was super critical of my work. But I said, “Well, I can do it, because this is the way people used to talk. And this happened a long time ago, Harry, so shut up.”

John Spong: Well, that’s one of the things that I love, and I hadn’t thought about it previously, but it really does place the listener—you know, not consciously, but it places us back in time. And this is that. And the same with the sailor verse—there’s some antiquated and very sailing-specific language there. It’s like you were Cormac McCarthy first, ’cause that’s his whole thing, right? Antique or antiquated language—you did it in this song. It’s just great.

[Kris Kristofferson singing “Highwayman”]

Jimmy Webb: Well, I did it on the spur of the moment, like I really do everything. It’s always instinctive with me, and I just go there. And sometimes it works, and honestly, sometimes it doesn’t work at all, and I get a lot of flack for it. Like, sometimes I think I never should have put that cake out in the rain. But when you look at Bob Dylan’s work, the non sequiturs and the lyrical mysteries that proliferate in Bob’s songs, and for that matter in the Beatles’ songs of the same period—and Procol Harum comes to mind as well—you know, I think that we were all doing that. We were all, like, kind of into an impressionistic genre for a while, influenced by hallucinogenics, but not exclusively because of hallucinogenics. It was because it was a fashion; it was a way of writing lyrics.

Then you had people come along like Joni Mitchell and James Taylor, that started grounding things again, really putting the roots back in the dirt. But for a while there, it was very euphoric, and it was chain of consciousness. This will be about whatever it’s going to be about; I don’t know what it’s going to be about. You know, that’s the way it was for a while.

John Spong: I just realized, having listened to this song all the time, and knowing it since I bought the cassette tape when I was in high school, that another thing you do in there with those lyrics, is after each one introduces themselves in their incarnation in that moment, you have the same rhyme afterwards. “Along the coach roads I did ride . . . I was born upon the tide . . . Across the river deep and wide . . . Steel and water did collide . . . Across the universe divide.” There’s an implicit continuity in there, that I’ve never even thought about, that is as plain as day. And it’s one more reason I guess I’ve always loved that song without realizing it.

Jimmy Webb: Well, thank you. It’s a device; it’s what I would call an inner rhyme scheme. And it’s something that I do, because I like detail. When I’m doing lyrics, I revel in the detail. So I wanted them to all rhyme, and in doing so, the rhymes pushed me along as well. It’s a two-way street—sometimes the rhymes push you towards the ideas. Sometimes in searching for a rhyme, you discover a fantastic idea.

John Spong: It bears out here.

[Waylon Jennings singing “Highwayman”]

John Spong: How did this song get to Willie, Johnny, Waylon, and Kristofferson? I’ve heard a lot of stories.

Jimmy Webb: Well, it’s because there are a lot of stories. When last we left “Highwayman,” it was on a Glen Campbell album. He put the album out, and I don’t know that very much happened with it. He had just met Tanya Tucker, and that was kind of spinning off. And I think people were paying more attention to Glen and Tanya than they were to Glen’s records.

John Spong: Did Glen’s own attention shift, or lack focus, through that period?

Jimmy Webb: Well, in more ways than one, even though I am not—definitely not going there.

John Spong: No, no, no.

Jimmy Webb: But in the meantime, the way that Marty Stuart tells the story, which I think is the definitive version, is that his cousin—Marty Gamblin was Marty’s cousin, and he was running Glen Campbell Music. So, there’s Marty Gamblin in charge of all this publishing. And Marty Stuart is in another place talking to Chips Moman and Johnny Cash, Kris Kristofferson, Waylon Jennings, and Willie Nelson about putting this album together. And as Marty tells it, everybody in the foursome knew each other except Johnny and Willie. They didn’t really know each other very well. The rest of them were kind of already connected. And so, the sessions weren’t going too well, and they were trying to find songs that they could duet on, or quartet on—it was four guys. And it was a great idea for a project, but materially speaking, it didn’t have an anchor. To hear him talk, it was kind of floundering at that moment.

And Marty heard “Highwayman.” And he called Marty Gamblin, his cousin, and said, “I hear you’ve got a song over there called ‘Highwayman.’ ” And Gamblin said, “Yeah, we do.” And he said, “Well, can you send it over to the studio right now?” So they did. And they’re all sitting around listening to it, and everybody’s wondering what Johnny Cash is going to say, or what Willie’s going to say, you know—there’s all this tension. And at the end of it, Johnny Cash said, “Well, I want to fly the starship.” And that’s the way Marty tells it. Forgive me, Marty, if it’s not right on, but I think that’s the way you tell it.

And I think that that is a kind of Rosetta Stone that sort of encompasses a lot of versions of this, including the one where Glen took it down to them. Well, he was there. And Glen always told me that he showed them the chords and stuff. 

John Spong: Oh wow. If I read, I know—because Waylon had cut a number of your songs at that point: “If You See Me Getting Smaller,” “MacArthur Park,” and I don’t know the others, but I know those two for sure. And I guess Glen had supposedly played “Highwayman” for Waylon at one point earlier, and Waylon was like, “I’m not sure that I get that.” But when they get it in front of the group . . . and there’s this idea too that the four of them, they have such distinct voices. And oftentimes with duet partners, you want to be the Everlys, and these guys were not going to be able to have their voices blend like that.

Jimmy Webb: Yeah, that was the wall—they were kind of pounding their heads against that wall. And this song showed up, where there were four verses and there were four guys, and they could just do their thing. 

John Spong: Yeah. And so, when they’re in the studio, Willie’s kind of got to go first, right? I mean, tell me about those voices and what they bring to the song.

Jimmy Webb: You know, I don’t know. They split it up themselves. Like I said, I think Johnny Cash wanted to be the starship captain. And I think they worked it out pretty well. Willie was the outlaw. Kris Kristofferson was the sailor. Which, if you look back on some of his film roles and things, you’ll find that. And Waylon was always this bear. He was a bear. He looked like he could build a dam all by himself, you know? So, I mean, that was just easy peasy. And then that pulled Johnny in to be the last guy, which I think they wanted him to be. But the end result was a hit record for them, and a kind of shot in the arm for my career. I got right back on, you know, the call list of guys to call. So I was happy.

[Johnny Cash singing “Highwayman”]

John Spong: When did you become aware of Willie? So, the big hits, those monster hits with Glen Campbell are in the late sixties. “By the Time I Get to Phoenix” is ’67, “Wichita Lineman,” ’68, “Galveston,” ’69. Are you already aware of Willie at that point?

Jimmy Webb: Well, I always knew about Willie.

John Spong: How’s that?

Jimmy Webb: Because you’d have to be deaf, dumb, and blind not to know about “Crazy.” And it was such a great song, and everybody would say, “Well, you know, who the hell wrote that?” I mean, talk about a stone-cold hit coming out of the gate. So I mean, I knew his reputation as a songwriter, and then I always admired the way he just brought his singing to the music. He never altered his approach to fit any particular song. He just sang the way he sang, and played the guitar the way he played. And there was a guy-next-door quality to it. It was clearly, to me, that he was a songwriter who was singing, as opposed to, you know, a trained vocalist, which, I mean, there’s a world—there’s a chasm, world of difference between trained vocalists and guys who sing. But Willie had kind of a next-door voice that was pleasant to listen to; it was authentic. Because there was just such an honesty about the voice. I tried to do that, and failed at doing it, but he had it. He had the stuff.

John Spong: I was going to ask, ’cause as someone who’s had so many great, and such great singers interpret their songs, there are some that are really deliberate with their phrasing choices and their harmonics and stuff like that. But Willie, whatever he’s doing, he sounds like he’s just doing his thing and being Willie.

Jimmy Webb: Well, I think he is. He came in, and I wrote this song for Waylon called “If You See Me Getting Smaller, I’m Leaving,” which is something that Willie—’scuse me, that Waylon used to say a lot, which was really, really funny.

John Spong: Oh, really?

Jimmy Webb: Well—“If you see me getting smaller, I’m leaving.” He used to say it all the time. And so—I loved the guy, and so I wrote this song, “If You See Me Getting Smaller, I’m Leaving,” and he recorded it. And when I was doing my Nashville albums—or some people call them my duet albums—Waylon sadly had passed on at that point, and Willie came in early one morning and recorded “If You See Me Getting Smaller” with me. And it was a one-taker, you know—I wasn’t even in the studio. My producer, Fred Mullin, he said he heard this big noise from the bus, the brakes, you know, the compressed air sound of shoosh. And Willie sort of materialized in the door. And he said, “All right,” he says, “where are we doing this?”

And Freddy put him on a microphone, and he sang, his verse was, “Willie, you’re my constant companion / And you know the light and shade / And we’ve spent a million dollars / To find out what we made / And we have made the maidens marvel / With the things we do and say / Down, down and out, brother, up, up, and away.” He sang that: “If you see me getting smaller, I’m leaving / Don’t be grieving.” You know. That’s the way Waylon was. And according to my producer, he sang it once. And he said, “Well, is that all right?” Freddy said, “All right.” And he said, “Well, tell Jimmy I love him,” and he was gone. Vroom, the bus pulled out.

[Willie Nelson and Jimmy Webb singing “If You See Me Getting Smaller”]

Jimmy Webb: So, I honestly think that that really is Willie. And my impression of him is that he’s not gonna—and I don’t mean this in a derogatory way—he’s not gonna work too hard on something, because then it loses its Willie-ness. It loses its Willie quality if you have to sing it more than three or four times. He just sounds like he’s singing in the living room, and he’s on his way somewhere else.

And it’s just such a simple formula—he plays the guitar and sings those songs, and people love that. There’s no complexity to it; there’s no production thing to wade through to get to the lyrics. The lyrics are right there in front of you. And they better be right. Because I wrote a song for him one time that, he told Chips Moman, he says, “I don’t hear these words coming out of my mouth.” So that one didn’t get recorded, which, ugh, is like an arrow, because you want that Willie Nelson cut, really bad. But after he turned it down, I was listening to it, and I was going, “He’s right; he’s right. It doesn’t sound like him.”

John Spong: One last thing. Since Willie might hear this, ’cause I know he’s heard some of these episodes, are there any Jimmy Webb songs you’d like to hear him sing?

Jimmy Webb: Well, I have quite a few of them, actually, now that you mention it. Like I said, you know, Willie’s always on the move, but it would be nice to sit down with him sometime and just kick songs back and forth, because I know he hasn’t heard half of my songs, and I’m sure that—I’m pretty sure I’ve got one in there for him someplace.

John Spong: I think he’s done a couple of Sinatra tribute records in recent years. And if he did “Didn’t We,” that would be breathtaking.

Jimmy Webb: Yeah, I think that would be a great one.

John Spong: And then one of my other favorite songs of yours, “The Moon’s a Harsh Mistress.” If he did that—because you also have to figure in, like, time of life, as he’s singing. If he did “Moon’s a Harsh Mistress,” that would have such a great, like, “what I’ve learned” quality to it. That also is such a great song, and to hear him picking on it . . .

Jimmy Webb: Well, Willie, I hope you’re listening in there, because I’m hearing the germination here of a great album, a great album for Willie Nelson.

John Spong: [Laughs] Oh, I’m with you right there. That would be so cool. That’s fantastic. That’s so great. Again, I can’t tell you how grateful I am.

Jimmy Webb: Thank you. And good night, Willie, wherever you are.

[Highwaymen singing “Highwayman”]

John Spong (voice-over): All right, Willie fans, that was the incomparable Jimmy Webb telling us all about “Highwayman.” A huge thanks to him for coming on the show, a big thanks to our sponsor, White Claw Hard Seltzer, and a big thanks to you for tuning in. If you dig the show, please subscribe, feel free to tell a couple friends about us, and visit our page at Apple Podcasts and give us some stars. Please also check out our One by Willie playlist at Apple Music.

Oh, and be sure to tune in next week to hear one of the absolutely essential figures in Willie’s long career, harmonica player Mickey Raphael, talk about the seldom-recalled 1972 song that first made him think there might be a place for him and his harmonica in Willie World, “The Words Don’t Fit the Picture.” . . . We will see y’all next week.