John Prine: The American Songwriter Interview

September '78 album art

Now for the first time here, the full interview which Rolling Stone called “a master-class in songwriting.”

This interview was conducted for this magazine in 2009. As I’d spent a lifetime learning and loving and absorbing his songs, it is quite extensive, requiring us to cut and condense it considerably to fit into our print magazine.

So we are happy to bring you, for the first time here, the entire
conversation with this genius of song.

Rolling Stone, in the immediate wake of John’s death, wrote of this interview in a tribute:

“John Prine was a humble guy who didn’t give a lot of interviews,”
they wrote, “But his interview with Paul Zollo is a master class in songwriting.”

They quoted from it, including one of the many luminous moments of songwriting wisdom he shared with us. The Washington Post and several other publications also quoted from it.

Calling it a master-class did smack of some hyperbole. But it’s not untrue, because anytime John shared his insights on songwriting, it was golden. He implicitly understood aspects of this mission from the very start that many songwriters never reach. It was one of many unlikely, and somewhat miraculous things about the guy.

In this passage which they quoted, John spoke of a dynamic that distinguishes his songs: his ingenious use of poignant, physical imagery. (Of which, examples abound: the old trees that just grow stronger in “Hello In There,” the flies in the kitchen from “Angel from Montgomery,” the broken radio in “Sam Stone.”)

From Rolling Stone:

“I think the more the listener can contribute to the song, the better; the more they become part of the song, and they fill in the blanks,” Prine told Zollo. “Rather than tell them everything, you save your details for things that exist. Like what color the ashtray is. How far away the doorway was. So when you’re talking about intangible things, like emotions, the listener can fill in the blanks and you just draw the foundation. I still tend to believe that’s the way to tackle it today.”

My current work continues on a written tribute for John which is about as long as Moby Dick now, and doesn’t seem like enough. Don’t worry – I will cut it down, and complete it. But it’s just been too damn sad right now to get it right. Hell, I’m still sad about losing Steve Goodman, who was John’s best pal and another Chicago hero. And we lost Stevie decades ago. But his absence always was hard to accept. And now this. John was always the survivor, the one who remained, honoring Goodman’s legacy while gradually becoming one of the world’s most revered and beloved songwriters. (Which would have made Steve so happy.)

Because as all these years have passed, a slow but sure expansion of awareness of the singular Prine greatness has become more pronounced, and our friend from the “land of the windchill factor,” became a living legend. Deservedly.

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So although the man isn’t officially among the living anymore, his legend is even greater. Like Lincoln, another Illinois hero, John belongs to the ages now.

But still, it’s tough for us, and for all his fans and friends. I revered him and, like many, considered him a teacher, and a personal hometown hero; he was also part of my life from that first album on. I lived in his albums, went to his shows, celebrated his Chicago greatness as the world discovered him, studied his songs seriously, and wrote a lot about him.

I was heartened by how many people loved this interview. The best review of it came from John’s beloved wife, Fiona, who was his champion to the end, and one of the best things to ever happen to John Prine. “You sure know the measure of the man,” she said.

When John’s late manager Al Bunetta read it, he called to tell me he loved my passion for John, and invited me to work on a Prine documentary, which i did for more than a year, on and off. We did filmed interviews with every important living figure in his life, his family, his band, and many other legendary songwriters who were happy to share all the reasons John Prine mattered; Bruce Springsteen, Tom Waits, Roger Waters, Bernie Taupin and others all said yes to our invitation, and talked about John on camera with us.

When Al died, all our footage was put away, and has yet to be edited. Hopefully that day will come soon. But working on it allowed me to spend more time with John, and I got to know him even better. (Thank you Al.) Which was a delight. Even in real life, he was seriously hilarious. But in a gentle, Midwestern way, always happy to make fun of himself. He was very serious about songwriting and his work. But he never took himself too seriously, which was charming.

So this loss, especially coming as it did in this sorrowful season of the pandemic lockdown, had been awful to accept for so many of us. There’s the feeling that this world just doesn’t make much sense without him.

But he left us a universe of miracle songs. Songs into which his warm, whimsical spirit was injected fully and will always remain. And for that we remain grateful.

Here is our full 2009 interview with one of America’s greatest songwriters, our beloved pal John Prine.

“You can write about anything. Anything at all. As a matter of fact, the less familiar, the better.” (Photo credit: Estelle Massry Photography)

STRAIGHT FROM THE STREETS of Maywood he came, a mailman with a chain of masterpieces. It’s Chicago, 1970, and word starts circulating around this close-knit folk music scene that there’s a new guy who must be heard to be believed. A songwriter who seems to have emerged fully formed with a voice like Hank Williams and songs that resound like some miracle collaboration between Woody Guthrie and Hemingway. His name’s Prine. And almost as soon as the Old Town denizens of the Windy City learned of him, the secret was out, and John Prine belonged to the world.

He was then and remains today a genuine songwriter’s songwriter – in that he’s written the kind of songs other songwriters aspire daily to write. Evidence of which is the vast array of covers of his songs by his peers, including Jackson Browne, Bonnie Raitt, Johnny Cash, Rickie Lee Jones, Willie Nelson, and so many others.

Even Bob Dylan, since the first night Kristofferson brought Prine and Steve Goodman into their Greenwich Village fold, has been awed. “Prine’s stuff is pure Proustian existentialism,” said Dylan. “Beautiful songs… I remember when Kris first brought him on the scene. All that stuff about `Sam Stone,’ the soldier junkie daddy, and `Donald and Lydia,’ where people make love from ten miles away. Nobody but Prine could write like that.” Kristofferson, despite unleashing Prine’s genius on the world, admitted to being intimidated by him. “He’s so good,” Kris said, “we’re gonna have to break his fingers.”

            When Prine and Goodman returned to Chicago after landing their deals, a celebration ensued for our local heroes, the entire town welcoming them with warmth and open arms. Unlike other big cities that reject locals who leave to make it big, Chicago has nothing but pride for those who come from our streets and take on the world. “We were like astronauts coming back from the moon,” Prine said. “They might as well have thrown a parade for us.”

            Prine’s lines are so evocative, so purely precise and finely etched, that they linger in our hearts and minds like dreams, separate from the songs. There’s the rodeo poster from “Angel from Montgomery,” the hole in daddy’s arm and the broken radio (from “Sam Stone”), the old trees that just grow stronger (from “Hello In There.”) The kinds of lines you carry around in your pocket, knowing they’re in there when you need them. His is a prodigious gift for capturing intangibles with language, such as the anomalous texture of Sunday nights he translated into “The Late John Garfield Blues” or the ennui expressed so purely with the flies buzzing around the kitchen in “Angel from Montgomery.”

Whether writing about old folks so sorrowfully isolated that people call “hello in there” like talking to a kid in a well, or taking on the phenomenon of celebrity through the unlikely subject of Sabu the Elephant Boy, Prine has melded his staggering penchant for detail, his proclivity to be both hilarious and deeply serious (and often in the same song), with a visceral embrace  of roots music. And doing so, he’s made the kinds of songs nobody ever dreamed of before, or since. 

            As a kid his first musical love was country; endlessly spinning the Roy Acuff and Hank Williams 78s in his dad’s collection, and tuning into WJJD out of Chicago to hear Webb Pierce, Lefty Frizell and others “back to back, all night long.” Roots music with stories to tell, the kind of songs he’d become famous for writing. And then a new kind of music arrived: “I was coming of age just as rock and roll was invented,” he said like a kid on Christmas, and along with his country heroes he added Elvis, Little Richard, Fats Domino, and the one he loved the most, Chuck Berry: “Because he told a story in less than three minutes,” Prine explained. “And he had a syllable for every beat… Some people stretch the words like a mask to fit the melody. Whereas guys who are really good lyricists, have a meter so that the melody is almost already there.”

            He started playing guitar at 14 – mostly old folk tunes taught to him by his brother Dave, who gave fiddle lessons. He quickly surmised he could take the same three folk chords and with a little rhythm play Chuck Berry, but his limitations then, as they have ever since, led him to his own songs. “I learned to write because I’d learn to play a Fats Domino song, say,  and it wouldn’t sound nearly as good as Fats Domino. So I’d just make up my own melody and write my own words. And anything I made up came out sounding like a folk song, because that was the kind of guitar I learned. If my brother would have been into Chuck Berry, then maybe I would have written all those songs as rock and roll shuffles.”

            When he was old enough, he got a job as a postman, which he loved, because he could write songs while walking the familiar blocks.  “It was like a library with no books,” he said. “When you’ve got your own mail route, day after day, it was an easy place to write.”

            For a string of consecutive Sundays he started coming to the open mike nights at the old Fifth Peg, a folk club on Armitage in Old Town. When he summoned up the courage to perform, he played his handful of unheard classics – “Angel from Montgomery,” “Hello In There,” and “Donald & Lydia” – and the audience was stunned speechless and forgot to clap. He figured he’d failed: “They just sat there. They didn’t even applaud, they just looked at me. I thought, `Uh oh. This is pretty bad.’ I started shuffling my feet and looking around. And then they started applauding and it was a really great feeling. It was like I found out all of a sudden that I could communicate. That I could communicate really deep feelings and emotions. And to find that out all at once was amazing.”

            And the word spread like wildfire. When Kristofferson heard Prine and Goodman, he pulled some New York strings and landed them both record deals. The rest is singer-songwriter history. It was 1971, the dream of the Sixties was over and Goodman and Prine emerged with a new kind of song, eschewing the lyrical abstractions of the past to write instead story songs about real people – “Midwestern mindtrips to the nth degree,” as Dylan put it. Songs with the concrete details and imagery of a novelist, but compounded, like those by his hero Chuck Berry, into three-minute masterpieces.

            We spoke to him on a sunbright Tennessee morning, his voice a low, raspy whisper since his recent bout with cancer and subsequent throat surgery. But his stories were punctuated with frequent laughter – laughter at himself, and at the sad folly of a world he’s written about so well for decades.

Perhaps recognizing that things he’s put off forever, like doing this kind of interview, were worth doing now or never, he took a long time to generously delve into his personal history from the streets of Maywood to Germany to the Chicago folk scene to the nightclubs of New York and beyond. Though talking wasn’t as easy as it once was, he enjoyed rummaging through the rooms of his own memory, which he found easier to do than recalling what happened last week. “I just gave a long interview yesterday to PBS,” he said, “so I might get confused. Sometimes it’s hard to separate yesterday from today.”

In the green room of the Grammy Museum rehearsing “The Speed of the Sound of Loneliness” with Sturgill Simpson. Photo by Paul Zollo/American Songwriter.

AMERICAN SONGWRITER: I’m so happy to finally speak to you. Growing up in Chicago, you and Steve Goodman were my heroes.

JOHN PRINE: [Laughs] Man, it was a great place then. I love going back to Chicago. Man, it was a good amount of fortune. That Steve and I came along when we did, and got into the Chicago folk scene. It was kind of all ready for us.

It was a great scene for songwriters back then.

It really was. It was just great to see all that blossom. All the people coming from all over, and playing at the open stages at the Earl [of Old Town]. Then Goodman took me to New York and showed me all this stuff that I read about, the clubs, the coffee-houses, that whole scene. And that all sprang both me and Steve’s record contracts. It was really exciting times.

I remember well hearing about you – this mailman from Maywood – and then the first album came out, and every song was a masterpiece. It was a stunning debut. Did you have those songs for a while before recording?

I really started writing when I got out of the army in 1968. And went back to the post office – I had done a couple of years in there before I got drafted. So I went back there to work. Especially when you’ve got your own mail route, day after day, it was an easy place to write. It was like going to a library with no books. You’re afforded to just go do your job, and you don’t really even have to think about it. You know you’re on the right street and you’re at the right house, and you’re putting the mail in the right box. That’s where I wrote a lot of the early songs, walking on the mail route.

Did you write your first song after you were in the army?

No, I wrote a couple early on. I learned to play the guitar when I was 14. I learned three chords and didn’t bother to [laughs] learn much else. It got to where, if I wanted to learn a song and it had a minor chord in it, and I really wanted to learn that song, then I’d learn it and the first thing I’d do is take the odd chord, as I called it, the one I had never played before – and put it in a new song of mine. Just to see where it would fit. See where you’d have to go emotionally for that to work.  People would always tell me about minor chords – when you’re writing a song, to put a minor chord in. For me, it’s like doom, you know. You know somebody’s gonna be extremely sick or die if there’s a character in the song. If it’s a first-person narrative, that you’re gonna go off to war or something. [Laughs] Something bad is gonna happen when the minor chord hits.

That’s funny, cause throughout all your songs, there’s hardly one written in a minor key. They almost always start with a major chord.

I wrote in a minor key a couple of times over the years. Mainly just to experiment. Because I always felt that if you start something in a minor key, then you’re already down in the mine. [Laughs] You don’t have to go to the mines, you’re already there. [Laughter] Because you’re in the minor chords.

Do you remember what your first three chords you learned were?

Probably G, C, D. It may have been A, D, E because they’re easier. I shied away from B7 for a long time because it took too many fingers. [Laughs]

“Hello In There” has that C maj 7 chord in it, and has more chords than you ever use.

I remember specifically when I wrote it, I think I had learned recently “Nobody Knows You When You’re Down & Out.” It had about nine chords to it. I learned the song more or less as a lesson so that I could sing and change chords quickly at the same time. And once I did that, I thought, “Gee, I’m gonna write a song with every chord in it I know.” And that’s “Hello In There.” And I’m still surprised to this day that the chords came out that well and sound as pretty as they do.

“Hello In There” is about old folks, yet you wrote it as a young man with a lot of insight into what it’s like to be old.  Do you remember where it came from?

“I wanted to hear what was in somebody’s purse…I wanted to hear what paintings were hanging on the wall. I wanted to know whether it was a cheap refrigerator.”

I just always felt, even when I was a young child, I felt really close to my grandparents. And later when I was a teenager, I just felt like a kinship with older people. And I remember for a short time I had a best friend when I was about 11, he had a paper route and he’d give me a couple bucks to help him with the route. And one of the streets I had had the Baptist Old People’s Home on it. And you’d have to park your bike and go inside with about twenty papers to the room where the people subscribed to the paper.

And some of the people, I guess, they didn’t have many visitors. And to their other friends in the home you were like a nephew or a grandson. I picked up on that and it always stuck in my mind. I guess that’s what it’s like inside of any kind of institution.

Just the title, “Hello In There,” is so evocative, as it implies that the person is deep inside himself, hard to reach.

I do vaguely remember that I tied it somehow to the first time I heard John Lennon sing “Across the Universe.” He was already putting a lot of echo on his voice on different songs, you know, experimenting with his voice, I played that song over and over again and it sounded to me like somebody talking to a hollow log or a lead pipe. With that echo.

And I was thinking of reaching somebody, communicating with somebody, like “hello… hello in there…” You know? When I was writing the song, I thought that these people have entire lives in there. They’re not writers, but they all have stories to tell. Some are very, very down deeper than others. See, you gotta dig, you know? And that was all going through my mind when I wrote “Hello In There.”

I didn’t know what the song was gonna be about, actually, when I came up with “Hello In There.” I knew it was gonna be about loneliness and isolation. I was still very much into using names [in songs]. I was a big fan of Bob Dylan early on, and his song “The Lonesome Death of Hattie Carroll” was a big model for me. I modeled “Donald & Lydia” after that song. As far as telling a story and having the chorus be the morale to the story. A wider morale than what the story’s saying. Like where the chorus is all-consuming, and a much bigger subject than what you’re detailing.

Yeah, that was much in the same way that any upbeat song I modeled after Chuck Berry, I modeled a ballad after specific songs, and that song of Bob Dylan’s, “The Lonesome Death of Hattie Carroll” to me was to be held up as a real model for songs, as was a lot of Hank Williams, Sr. songs.

It’s surprising to me to hear the influence of Lennon and also Dylan to some extent, in that many of their songs were quite poetically abstract and surreal, whereas your songs tell clear stories with precise imagery.

Yeah. I don’t know how I made that decision. It’s what I was good at, but I might have thought it was a fault at first. I might have thought I used too many words to discuss a minor detail. But I soon found out that the reason that was on my mind is because that’s what I wanted to hear. I wanted to hear what was in somebody’s purse. I wanted to hear that at the time of this emotional thing. I wanted to hear what paintings were hanging on the wall. I wanted to know whether it was a cheap refrigerator. [Laughs] I just did. It was kind of detective work.

You’ve always been one of the best at using pictures as symbols, like the old trees that just grow stronger in “Hello In There,” or the rodeo poster in “Angel from Montgomery.”

[Pause] Yeah. I’m not sure where that came from. But I’m glad it did.

“You let the character write the song. You just dictate from then on. You stick to it, and whatever the character is saying, you have to figure out how to keep that in the song. That’s how I do it. I almost go into a trance.”

Was “Angel from Montgomery” also one you wrote during your postman years?

Yeah. That was almost a co-write. With a guy named Eddie Holstein.

I knew Eddie. And his brother Fred.

God, sure. I knew Fred since I was 14 and was first going to the Old Town School, Fred used to work part-time in the store. Every time I wrote a song Fred would turn on his really good high-class tape recorder, reel-to-reel, and record it. So he’s got recordings of me on guitar singing all my songs in his apartment long before I ever recorded for a recording company. I never found out what happened to the tapes.

But Eddie and me, we used to go to lunch together because I used to like to watch Eddie eat. He’d eat for hours. And he was just a little skinny guy then, and you’d wonder where the food was.

Eddie said, “Why don’t we write a song together?” And I said, “Jeez, I’ve never written with anybody. But I guess we could try.”

So we went over to his apartment, and I said, “What do you want to write about?” And he said, “I really like that song you wrote about old people, let’s write another song about old people.”

I said, [laughs], “I can’t, Eddie, I said everything I wanted to in ‘Hello In There,’ I can’t do it.”

So I thought for awhile and said, “How bout a song about a middle-aged woman who feels older than she is.”

And Eddie goes, “Naw.” [Much laughter]

But the idea stuck with me, and when I went home I started “Angel From Montgomery” that night. With the words “I am an old woman named after my mother.” I had this really vivid picture of this woman standing over the dishwater with soap in her hands, and just walking away from it all. So I just kept that whole idea image in mind when I was writing the song and I just let it pour out of that character’s heart.

That song was like a lesson for so many of us songwriters about how to write in character. I can remember hearing the song the first time with that opening, “I am an old woman” and thinking what an extraordinary way to start a song, especially written by a man.

Again, I didn’t realize all this at the time, but if you come up with a strong enough character, you can get a really vivid insight into the character that you’ve invented. You let the character write the song. You just dictate from then on. You stick to it, and whatever the character is saying, you have to figure out how to keep that in the song. You know? That’s how I do it. I almost go into a trance. Once I’ve got an outline, a sketch in my mind, of who the person was, then I figure I’d better let them speak for themselves. Rather than me saying, “Hey, so here’s a middle-aged woman. She feels she’s much older.” It wouldn’t have been nearly as effective.

I got asked years later lots of times how I felt I could get away with writing a woman’s song first-person. And that never occurred to me, because I already considered myself a writer. And writers are any gender you want. You write from the character and how can you go wrong?

 But there aren’t a lot of songwriters, outside of Broadway, who write effectively in character. You do it, and Randy Newman does—

I love the way Randy does it. The character stuff, so determined that they believe what they’re saying. I got to tour with Randy a lot early on. We did a lot of shows together, just him on piano and me on guitar.

You’re similar not only that you’re great at character songs, but also can be funny in songs, which isn’t easy. You’re both very serious and very funny.

Yeah. For me, I find humor in just about every situation. Even the most serious situations. And I find if you use it right, it allows the listener not to feel so uncomfortable. Or to even empathize with that character.

With “Angel from Montgomery,” do you remember where the title came from or why you placed it in Montgomery?

No, I can only guess like other people. I’m so far away from myself; I’m removed when I’m writing.

Eddie always kidded around and told people, “Yeah, I wrote half of that and John just bought me lunch.” [Laughter]

Eddie thinks I got it from the angel down on Michigan Boulevard [in Chicago]. There was evidently a gargoyle that came out from the Montgomery Wards building. But I’m prone to think that it’s because I was a huge Hank Williams, Sr. fan and I knew he was from Montgomery. And I think that’s where I thought the woman was from in this image that I had, this woman with the soapsuds on her hand. She lived in Montgomery, Alabama and she wanted to get out of there. She wanted to get out of her house and her marriage and everything. She just wanted an angel to come to take her away from all this. And her memory of this cowboy she had once – or whether she had him or not – it doesn’t matter now.

Yeah, you’re not only in her real life, but in her dreams, in what she’s yearning for.

Yeah. Man, they did a book of the famous poster people here in Nashville, the ones who did those giant posters of Hank Williams and the Grand Ol Opry and everything. They’re still going today with the original presses. It’s a great place to go. It’s not far from the Ryman Auditorium. They put a book out of their famous posters. And the poster on the cover is a poster of a rodeo, a guy with a bunking bronco and it’s got the words to the beginning of “Angel from Montgomery” on it. And it’s a really good looking poster. I asked them to give me a copy of it. It looked very much like whatever I had in mind when I wrote it.

I remember as a kid listening to that song and learning so much about how you set the mood – instead of saying she’s bored, you say, “There’s flies in the kitchen/I can hear em there buzzin’/And I ain’t done nothin’ since I woke up today…”

I think the more the listener can contribute to the song, the better; the more they become part of the song, and they fill in the blanks. Rather than tell them everything, you save your details for things that exist. Like what color the ashtray is. How far away the doorway was. So when you’re talking about intangible things, like emotions, the listener can fill in the blanks and you just draw the foundation. I still tend to believe that’s the way to tackle it today.

Whenever I co-write with people – and it’s very difficult to dodge co-writing in Nashville [laughs] – I tell people I’m just trying to write with myself right now, and it’s very difficult to jump back and forth between the two. Because I enjoy co-writing when it’s with the right person. I can go into a different head with a co-writer. Let them take the song on and I’m just helping them with their idea. But if I’m gonna write my idea, I want to stick with it myself. I usually won’t be the one to initiate a co-write.

The old cliché for writers is “write what you know.” Yet you seem to reach beyond your own personal experience often. A song like “Sam Stone,” about a man who comes back from Viet Nam a junkie, is that someone you knew?

Well, I had just gotten out of the service myself. I got drafted with about six of my best friends, and some of them got sent to Viet Nam. Everyone I knew, they got back, they came back. I knew two kids I went to school with who didn’t come back from Viet Nam. In fact, they didn’t last a week there. But my own personal friends, they all came back. But there were big changes in their lives. And there are still to this day.

I remember when they first came back, whenever it seemed appropriate, I would question them about how it was there. I pretty much got the same story from everybody, that it was pretty much a wait and see situation over there. You could be in a place in Viet Nam where there seemingly wasn’t much action, you weren’t anywhere near the front. But it soon became evident that there was no front. There was always a front as far as if we made an invasion or they did and there was a battle going on, there was that.

But the whole place was the front. You could be walking over to the officer’s club for a drink some night and step on a mine. Or nothing would happen for six months, there wouldn’t be a sound, and all of sudden you’d be walking around and they’d come over and bomb. And that kept you on edge, I guess, all the time.

I always thought one of the great mistakes they made in the service, I don’t know if they even tried to correct it with the guys coming back from the Middle East, but if they spent half the time that they do getting you ready, and the intensity that they put you through in basic training for combat, if they spent half that time bringing you down and teaching you how to be a civilian, it would make a big difference. I would liken it to a person who has done prison time. They all speak of, especially if they’ve been in for a very long time, of how difficult it is to be back on the street. And how difficult it is be to accept freedom once you get used to living incarcerated. So all my friends that were over there were affected, like I said. I wasn’t writing about anybody specific. I made up the character of Sam Stone, obviously, just cause he rhymed with ‘home’.

But I remember a story in the papers about some soldiers coming home from Viet Nam in San Francisco they landed. And some people at the airport – I don’t know if they were protesters or hippies, or what – but they were spitting on them. Saying they shouldn’t be over there killing babies and stuff. And I was totally repulsed by that. And here, mainly, I was against the way. And I was for all the hippies and didn’t mind burning the flag and stuff, you know? [Laughs]  I mean, to blame a soldier – maybe because I was one – I felt like, gee, you don’t know what you’re talking about. To blame the guys who are going over there. Because they didn’t run to Canada and say they’re not gonna fight for their country. But that just seemed really awkward and stupid to me.

So I wanted to explain through a fictional character what it might be like to come home. Not to be there, because I was never in Viet Nam. I was stationed in Germany. And I was drafted at a time when most people were being sent to Viet Nam, and I thought I was going there for sure. But when the day came that they gave me orders to go overseas, I was thankful for it. Whereas other guys who got sent to Germany, as soon as they got there, they put in for Viet Nam. They didn’t want to be in Germany, they wanted to be in combat. And I’d just say [laughs], “You guys are nuts.” [Laughs] It’s not John Wayne time.

I had my guitar over there, though I didn’t do much writing. I was about three bunks down from a guy who sang beautiful Lefty Frizell songs. He could sing just like Lefty. And he and I became fast friends. I sang Hank Williams songs and he sang Lefty songs. I think “Aw Heck” might have been the only song I wrote while I was over there.

Songs like “Sam Stone” and “Angel From Montgomery” are such mature, sophisticated songs for a beginning songwriter to write. Any idea how you were able to write at that level so early on?

No, I don’t. I was very nervous about singing the songs in public for the first time. Because I thought that they would come across as too detailed, too amateurish. Because I hadn’t heard anybody being that detailed. And I thought there must be a reason for that. I must not be doing it the right way, whatever the right way is. But I knew the songs were very effective to me. And they reached me. And I was very satisfied with the songs. But I didn’t know how they would relate to other people because I didn’t consider myself a normal person. [Laughter]

Did audiences take to them right away?

Right away. They were very effective. The first crowd just sat there. They didn’t even applaud, they just looked at me. I thought, “Uh oh.” [Laughs] I thought, “This is pretty bad.” I started shuffling my feet and looking around. And then they started applauding and it was a really great feeling. It was like I found out all of a sudden that I could communicate. That I could communicate really deep feelings and emotions. And to find that out all at once was amazing. Whereas it would have been different if I would have written a novel or something and waited two years till somebody to write me back.  And said, “I think we’re gonna take a chance and publish it.” That must be a whole different feeling. But mine was immediate. It was there before other people. Nobody knew me from Adam.

Do you remember the first song you wrote?

Yeah. I think I wrote two at the same time. I had a girlfriend whose father was a janitor. And the reason I’m telling you that is because he had access to a tape recorder, and nobody else I knew had one. They were really rare. A reel-to-reel. He got it from the language department. It was broken and he fixed it and had it at home. And I sat down and taped three songs for this girl and her sister. And the three songs were “Frying Pan,” “Sour Grapes,” and “Twist & Shout.” And I know I didn’t write “Twist & Shout.” [Laughter] Those were the three, and I made her a present of them.

Years later, I ended up marrying that girl. She was my first wife. She found the tape. It was after I had made the first album, so I put two of those songs on Diamonds In The Rough. And those were the first songs I remember writing.

You said you wrote “Sam Stone” and “Hello In There” when you were working as a mailman-

Yeah. That was only six months before I first got up and sang, and six months after that I got a record contract.

When you started writing those songs, was your intention to become a professional musician?

No, because I didn’t think that kind of thing happened to people like me. [Laughs] I thought that people that you heard records by were from a whole nother world. No matter what their biography says, they’re either French or from Britain or had rich relatives. [Laughter] And therefore I wrote the songs more for myself.

I was surprised that the songs connected as well as they did when I first sang them for an audience. I think I was more surprised than the audience. I just got the nerve up behind a couple beers one night to stand up onstage – cause it was an open mic – and the competition, the bar, was very low.

Which club was it?

The Fifth Peg, which was across the street from the Old Town School when it used to be on West Armitage. Before that it was on North Avenue. And there was always a club that the people from the Old Town School frequented. When they were on North Avenue, it used to be the Saddle Club. Which was a couple of blocks from The Earl. And when they moved over to Armitage, this club, the Fifth Peg, opened up across the street and featured folk music, and that would be the club where the people would gather after the classes. But the link was always the Old Town School.

I was writing these songs totally myself not thinking that anybody was going to hear them. And I went from that to being a very nervous public performer. Who had no voice whatsoever. I would kind of speak the words. Very fast or very slow, depending on how the melody went. And I’d hold certain notes [laughs] to let people know I was going to the next idea. And that’s about how limited it was. It was very painful for me to stand up in front of people and sing.

Meanwhile, I enjoyed singing. I would sit for hours just by myself and just bellow out and beat on the guitar. I loved the actual act of singing. But to listen to myself on tape or to sing for other people was really painful. And the first time people heard me [laughs], evidently they felt the same.

Steve Goodman was such an astounding performer—

He certainly was. I think Steve had arrived, except for timing. He really worked hard, and he was entertaining. He and another friend who played piano for me had an act before Steve was a single act. It was almost like Chad Mitchell trio stuff.. Steve did everybody else’s songs before he ever wrote “City of New Orleans.” I read the entire Clay Eals book [Steve Goodman, Facing The Music] so I should know.

I did as well. Clay’s a good guy, and that’s a wonderful book.

No kidding, man. The amount of people he interviewed for that book was amazing.

Yeah. He did Steve justice.

He sure did.  

 Did you learn much about performing from watching Steve play?

[Pause] Jeez, the way he handled an audience, you couldn’t help but pick up things. I might not have thought about it like that at the time. I developed my own thing from my own mistakes. What I considered my mistakes. My own nervousness. I made it an asset. That’s how I started talking between songs. And I found out that people liked the stories I was telling – they were just totally out of pure nervousness – I was trying to kill time till I had to start singing [laughs] those painful notes again. I put the two together – the talking and the singing – and noticed that worked.

You just find out things from your own shortcomings. It’s easy to say in hindsight, of course, and I never would have said this at the time, I didn’t think so, but that’s what I did – I gathered all my shortcomings and made them into the stronger points, you know, the points I could stretch cause they worked. You find out real fast when you stand just in front of twelve people what’s working or not. Sometimes it’s just the way you present it that makes it not work. It’s got nothing to do with the material.

Do you generally have an idea in mind before you start writing a song?

Yes. Because otherwise I don’t see any reason in sitting down [laughs] to do it. A lot of time I’ll have the song written and I only write it down so I don’t forget it. I could write behind a steel mill. But it’s easier to get behind a guitar.

You said that sometimes when writing it feels like a trance. Do you have experience of lines just coming to you, almost from beyond?

Yes. Sometimes they come so easily that you check yourself, you know? And the more you travel, the more I’ve been around music – like when you’ve been around 40 years around other songwriters’ music constantly – I go down to the grocery store and people drop CDs in my pocket — and so when I do get something, I got to check and make sure I didn’t hear that somewhere. And when I’m sure, I proceed, and I take whatever the image or the line is, I take that and I don’t try to fix it. I check it like a diving board, you know? And it’s like I’m gonna go swimming in their pool today.   

Is it easy for you to get to that place where songs start coming?

No. It’s very elusive. Patience. You gotta learn patience. I know that I’m basically a very lazy person. At everything, including writing. As much as I enjoy writing, I would rather do anything in the world but sit down and write.  But once I get into it, I’m into it. I mean, if you said, “Let’s go get a hot dog first,” I would always go for the hot dog. I wouldn’t go, “No, let’s finish this song.” [Laughter] I’d say, “Sure!” [Laughter] And I know that about myself. So I have to balance out my patience waiting for the right thing to come along with my laziness, knowing I’m trying to avoid working.

So you never force yourself to write—

No. [Laughs] No. Unfortunately a lot of your best first-person songs come from a person’s relationship, from something awful happening, like in your life, to someone you love very much. So you wouldn’t want to force those thing. Not for the purpose of a good song. Some guys I’ve met, I wouldn’t put anything past them. [Laughs] Some people, for a good song, might go through all kinds of changes to get to that.

Your songs seem to suggest you are having fun writing them, with the rhymes and the rhythms—

Once I get into it. And I almost need, not someone standing over me, I do need some prodding. I have to realize, jeez, okay, it’s been long enough without a record. Because I can afford just to go play my songs for big crowds. I play in some of the nicest places in this country. And they got nice dressing rooms. I’ve moved up to where the dressing rooms actually don’t have rats running around in them.  It’d be very easy to just keep doing that. But every once in awhile, I’ve got to write and get myself into a fresh state of mind. And I have to look forward, cause I know it’s gonna take a couple of years to process.

I don’t write ten songs in two weeks and go into the studio. I just don’t do that. I’ll write three songs and love them, and I’ll go sing them for a year and then write the next three. I just know how I am. Like I say, there’s nobody standing over me. I’ve got my own record company, my own publishing. I try and make a place for myself to write that I want to go to.

Having written such amazing songs right from the start, was there a sense after your first album that you had a lot to live up to?

Only after so many people told me that so many times. [Laughter]  

His miraculous debut.

A chain of masterpieces; the remarkable debut album, 1971.

And then I got to remember that the gift I have, I only owe it to myself to honor that gift. I don’t have to compete against myself. Because that’s crazy. Why try to write a better song about old people or a better song about a veteran coming home? Why try to update “Sam Stone”? There’s no reason to. So I try and stay true to wherever the writing comes from. And it comes from the deepest well of emotion. Whether it’s something political, something humorous, something that might break your heart, if that’s what’s down in the well, that’s what I’ll come up with.

You said you write songs in your car. Do you mean that you write music, too, or just words when you’re away from the guitar?

To me, the melody usually comes along hand in hand with the words. It’s very rare that I’ll get a little piece of music that I keep playing over and over, like something I’ll do at a soundcheck that I can’t get rid of. And in order to get rid of it, I’ll write a song to it. But usually they start with the idea or the image and I want to say one thing. Just one sentence. And I’ll figure out who would say that and how can I build a song on that?

Do you collect titles and think of titles before writing?

No, but funny enough, when I first started co-writing, at first I only wrote with really close friends who also happened to be songwriters. Just because I knew I liked spending time with that person, so I didn’t really care if I came out with a song or not. As long as we had a good time together.

One of the first people that I wrote with when I first moved to Nashville was somebody I didn’t know but I just wrote with because of all the great songs that they’d written was Bobby Braddock. He wrote “We’re Not The Jet Set,” “He Stopped Loving Her Today.”

So when Bobby and I got ready to write, we wrote “Unwed Fathers.”  The night before we got together, I said, “Do you like to start any particular way, Bobby?”

And he goes, “You know, if you feel like it, bring a little list of song titles.”  Just as a way to get started. We can go, “Naaaah…” [Laughs] “And that must mean we got a better idea.”

I was watching the Superbowl and I wrote down twenty titles. And I used five of those titles in the song. I used the title “Children Having Children.” And I pulled different ones I liked to go with that subject that I liked of “Unwed Fathers.” Sometimes there’s not titles, they’re just random thoughts you can associate with something else. I don’t like to waste paper. [Laughter]

I don’t like to write and throw it away. I don’t like starting over. Usually I write because it’s already kind of written in my mind. I may not know the words, I may not know the character’s name, I may not know any of that. But like I say, I get the picture. It’s a matter of me transferring it to paper.

You said it almost feels like it’s dictated to you from somewhere else? Any idea where that is?

No. None. I don’t know what the rules are. I don’t know if I ever cheated at the game. I don’t like to get so close to it. Every once in awhile it’s safer to go for a hot dog. [Laughs]

Some of the songs come so fully, it’s like their pre-packaged. There have been a couple that came in the middle of the night. And I thought, jeez, I’ll never forget that. And went back to sleep, and it was gone. You’ll hear something years later that another songwriter that you respect writes, and you go, jeez, I think that was the remnants of that song that got sent to me.

“I try and stay true to wherever the writing comes from. And it comes from the deepest well of emotion.”

Your songs seem so distinctive to you. Do you think someone else could pick up one of your songs?

Just the basic part. Like I’m saying, I get the picture and the emotion. And if you don’t grab that and pull it down and start drawing your drawing so you can show it to somebody else to see if they can recognize it, you can lose it. That’s why I say it’s like taking dictation. But like I say, where it comes from, I don’t know and I don’t care. [Laughs] I don’t care.

Many songwriters feel that songwriting is more a sense of following a song than leading it –

Exactly. Because if you approach it the other way, it seems that you are outguessing it. Like people who are trying to write hit songs are guessing what the public wants. Or worse, what the record executive wants.

One of your most beautiful and poignant songs is “Souvenirs.”

I wrote that in my car. A 65 Chevelle. Driving to the Fifth Peg. Like the 5th or 6th time playing there. I used to play there just Thursdays after they hired me. They hired me from that open stage the very first time I sang for the crowd.

They invited me back a week later, and I did it again for an open stage. And that night the owner asked me if I wanted to sing once a week. I didn’t know I was auditioning. I didn’t know what to do, how long you’re supposed to sing or anything. So I went home and wrote a bunch of songs to fill in the time. They told me to do three sets of 45 minutes. So about the fifth time I was driving down there I thought, God, the same people are gonna be sitting there. I better have a new song. So I wrote “Souvenirs” in the car on the way down. And then I thought I’d come up with a melody. And I thought I had come up with a pretty sophisticated melody in my head, and I was surprised to find out it had the same three chords that all my other songs have. [Laughter] Really surprised. I thought I had written a jazz melody.  

You’ve written several songs like that one, really poignant songs about time passing and what we lose in time — .

Yeah. Where any of that song came from, I have no idea what  the start was.           

Was there someone in mind you wrote it to?

I have three brothers, two older, one younger. And one of them was asking me about “Souvenirs” once. He was five years older than me and I remember once we were at a carnival and we were very small, and he got lost for awhile and I got very, very scared that I would never see my brother. I remember that. It was a different kind of scared than I had ever experience before in my life, like being scared by ghosts or creepy stuff. And I kept that emotion buried somewhere, and it came out in “Souvenirs.” How, I don’t know.I told him, “I remember you standing there holding a little plastic horse that you either won or somebody gave you. I put it all together in a picture, and that’s what came out..”           

Is it true that Bruised Orange” is a title you had long before you wrote the song? You also named your publishing company that.

Yes. When I was still a mailman, I had about eight songs, and somebody told me if I wanted to sing them in public, I should think about copyrighting them. And another fella told me that if I just copyrighted them all under one title, as a musical, then I could do it all for five dollars, instead of five dollars per song.

So I found this music professor from Northwestern and he would make the sheet music for a couple bucks per song. He’d write it out in music, and I’d include a cassette and lyric sheet and mail it to myself, get it postmarked, and that was considered a legal copyright. I put it all under the name “Bruised Orange.” [Laughs] Which I used many years later. That’s what I called the imaginary musical. They were all songs like “Sam Stone,” “Blow Up Your TV,” “Paradise.” I had them all under one title. I found it not too long ago, the envelope. I finally opened it. I had to. [Laughs]  I figured it was safe to do now. [Laughter].

I thought, jeez, I’m supposed to come up with a title for my musical. And I thought, I’ll just pretend. Cause I knew I could put all the songs under one name. Later somebody explained to me that all they do is give you a number. You could write “White Christmas,” and they just give you a number. I thought when you sent in a song to the government to be copyrighted that there’d be a thousand guys with a thousand pianos in a warehouse [laughs] and they’d play about eight notes of your song and go, “Sorry, man, that’s ‘Your Cheatin’ Heart.’” [Laughter] And then stamp it “reject.” But when I found out you could put them all as a musical, and [Bruised Orange] was just a name I came up with off the top of my head.           

I listened to the song “Bruised Orange” last night and realized that someone might normally call it “Chain of Sorrow,” as that’s the most prevalent line. How come you chose that title for that song?

I liked the title, and the image, and I wanted to do something with that image without saying anything about an orange or a bruise in the song.It was based upon something that actually happened. I was an altar boy, and the Northwestern train tracks were not far from the church that I went to. I was going down there one day and there was this big ruckus going on at the train tracks. I had to go shovel the snow off the church steps before Mass. Because they’d sue the church if people fell and broke their legs.So I was going down there to get the snow and ice off. I went over to the train tracks. A kid who had also been an altar boy at the Catholic Church, I found out later, was walking down the train tracks. And evidently the commuter train came up behind him. They were taking him away in bushel baskets, there was nothing left of him. There were a bunch of mothers standing around, trying to figure out – cause it was Sunday morning and all their kids were gone and they didn’t know – they all hadn’t located their children yet, and they didn’t know who it was.

I told that story on TV once, I was asked about that song when it first came out. And the family of that son lived near Madison, Wisconsin years and years later – 20 years later – just wrote me the nicest letter, and told me they recognized the subject. They gave me the date of when it happened, and that would have been around the time when it happened. And so it was just a vivid memory that I had, and I put it together with how I felt about my job as an altar boy. I was supposed to be the maintenance man at church and they were short an altar boy. They baptized me and confirmed me on a Saturday and Sunday I was wearing a robe, lighting a candle. Then I had to go early and shovel the snow as a maintenance man or cut the lawn in the summertime. And that’s when I bought my first guitar.

Listening to your songs, including great early ones like “Sabu Visits The Twin Cities,” it’s evident that you can write about anything in songs, using content nobody else ever has. Was that something you felt?

[Softly] Yeah. [Laughs] Definitely. [Laughs] If I could get away with the song about the veteran coming home, and a chorus like, “there’s a hole in Daddy’s arm where all the money goes,” even as powerful as it turned out to be, that I could write anything. But when I wrote it, it was very odd. When I’d sing that chorus, I’d be nervous and by the second time around, there’d be dead silence. And I just figured, yeah, you can write about anything. Anything at all. As a matter of fact, the less familiar, the better.

Many songwriters feel you have to write about yourself. Yet you’ve shown that isn’t the case – unless you feel you’re writing about yourself all the time?

There’s a certain amount of yourself in it, I’m sure. But as a writer you don’t need to be writing about yourself all the time. Maybe you’re not that interesting, really. Without an outside thing.

Was there ever content or an idea for a song you couldn’t get into a song, that wouldn’t work?

Yes, definitely. More often than not, I can’t jump into a song too quick. Because there’s always the danger of painting yourself into a corner. There’s no tougher corners to get out of than the ones that you paint. Because you can’t change the rules if you made up the rules. And then you get to the third verse that needs to be there, and you can’t define that line where you can just repeat the first verse. You can’t get out of it that way, so how are you going to get out of it? Especially if it’s a story song. You’d better be going somewhere [laughs]. I think that’s what the listeners are always thinking that, hey, this is precious time I’m giving you, so you’d better be going somewhere. [Laughs] This joke better be funny.

Do you generally write more and then cut stuff out?

“There’s no tougher corners to get out of than the ones that you paint. Because you can’t change the rules if you made up the rules.”

No, I edit as I go. Especially when I go to commit it to paper. I prefer a typewriter even to a computer. I don’t like it, there’s no noise on the computer. I like a typewriter because I am such a slow typist I edit as I am committing it to paper. I like to see the words before me and I go, “Yeah, that’s it.” They appear before me, and they fit, you know, and I can see that the line fits with the previous line and the line after it. I can see the inside of the song as well, not just rhyming the last word so that the song sounds right. I pretty much do that as I go. I don’t usually take large parts out. If I get stuck early in a song, I would take it as a sign that I might be writing the chorus and don’t know it. Sometimes you’re writing the first verse or second verse and you’re actually writing what you want to repeat. And you gotta step back a little bit and take a look at what you’re doing.

Do you write a song from beginning to end?

I guess now I do. I’m not sure if I always did that. Sometimes I feel it from the middle out. Where I realize that perhaps I wasn’t starting at the beginning. I just start with a character and I have to develop it more, so I have to go back and write a first verse or an introduction.

You said that in “Hello In There” you used all the chords you knew at the time. Have you ever done that with other songs?

Yeah, I still haven’t used that many. I think when I wrote “Storm Windows,” somebody had just taught me the Elvis Presley song, “That’s when Heartaches Begin.” And it had a Cm chord. And I really wanted to learn the song, so I learned a Cm. And I know how that chord feels. It’s the one chord that with a G, I know how it feels, what the emotions are there. So I felt I wanted to write a song that goes there and gets out of it, and that was storm windows.

When you’re at the typewriter working, do you use your guitar?

Sometimes. And sometimes when the melody is so apparent, I can just sit with just the words.    

Do you remember where the idea of writing “Sabu” – a song about the famous elephant boy – where that came from?

I know it was from somewhere else. Because it took me several weeks before I would play it for anybody. And the whole song came at once, just like it is, fully written. [Laughs] I didn’t know whether to show it to anybody or what, whether it was an ugly baby or what.

Being from Chicago, I always loved that line about “the land of the wind chill factor.”

[Laughs] Me, too. I know what gets me and I know what I like, and usually in the end I’ve got to go with that.


We were talking about funny songs, and there aren’t really that many funny songs that work over many years. The joke wears out. But your funny ones are still funny. Is that hard to do?

I never know until the years pass. [Laughs] I’m surprised as anybody. I pulled the song “Your Flag Decal Won’t Get You Into Heaven Anymore” out of mothballs. I stopped singing that when most of the thing with Viet Nam was over. People asked me about it, after we were in Iraq. I thought that if George Bush kept tinkering so much about patriotism, that if you talked out against that war, you definitely were a Lefty.

When he started with that bullshit, it really got under my skin. So I thought one night I would pull that song back out and start singing it again. I had no idea if it would work as well. And it felt really good, too.I have a lot of songs I haven’t touched in years. I need to be prodded to bring them out. I only have to play them once or twice to see if they work. It’s not even so much the crowd reaction. It’s more how I feel when I’m singing the song. I can just tell if I stopped singing that for a reason.  Maybe I’ll feel that I didn’t get everything right in that, or everything I could have. Cause I’ll never go back and change a song. I just feel that would violate it. But I’ve had an amazing track record of my stuff working – at least for me. Not only do I not get sick of it, but still for a large part I appreciate it.

We were talking about “Souvenirs,” and you said Steve Goodman used to play on that song, and –

Yeah, I can still hear him playing it. He played a back melody, so that you could barely hear the difference of who was playing. On tape or when we did it live. And I realized a large part of what he was doing was making it sound like I was playing the good part. [Laughs] And that’s basically the kind of guy he was. The kind of guy who wouldn’t need to shine the light on him, even though he could ham it up with the best of them.

He produced your Bruised Orange album. What was that like to have him produce?

He was definitely doing me a favor. I had made the record already but I didn’t have it. I worked with Cowboy Jack Clement, who was a huge mentor to me and the reason why I moved to Nashville. I moved there and we worked for three to four months, solid. And through all kinds of outside forces and things that shouldn’t have been going on in the studio, we didn’t get the record that we were playing everyday.

We really enjoyed making the record, but we didn’t get it on tape the way we were hearing it in the studio.This was the first one I was doing for Asylum Records, and they kept spending money on it. And Jack was on Asylum as well, and his record was about two years late [Laughs]. So these were both of our first records on this label, and here we were working on mine. And we were having a great time. And listening to music, too. It was a very musical summer we spent.Then I got involved with somebody, and it got to be a very sticky affair.

What I’m saying is that I had a record that I put my heart and soul into with the songs, and gone ahead and made the record, and I didn’t have anything to show for it. I had to walk away from the whole thing.So I went out to L.A. and I talked to, Christ, twenty different producers, really great guys, great producers. Big-time producers. And I just didn’t want to do it. I just didn’t have the heart to do the record again. And Goodman said he would do it.

And I said, “Well, just don’t look to me to approve or disapprove. I’m just totally… numb.” I said I’d come in and do anything, you just tell me what songs to do today and I’ll do it, and if you say it’s done right, I’ll believe you. I totally put it in his hands.And he handed me back a beautiful record. So that’s the way that that one went down. It was no fun for Steve, I’m sure. I was not a fun guy to be around. [Pause] Anyway, that’s the name of that tune. [Laughter]Funny how things turn out. Steve, he was a tough producer to work with.

How so?

Very stubborn. I think because he knew me so well. If someone doesn’t know me, they kind of keep at a distance. Which is fine with me. [Laughs]  But he knew me. So he would push me. Some nights at the studio I’d say, “Steve, get off my back, man.” But he knew what he was going for.

Do you remember the first time you met him?

Yeah, I met him briefly the first time with Fred and Ed [Holstein]. He came to check me out. He didn’t stay long enough to say hello after. They just kind of ducked in and ducked out and went back over to the Earl. And I started going over to the Earl to check it out on the nights I wasn’t playing at the Peg.

Goodman came up to me one night, walked up to me – this is the first conversation we ever had at any length – they were already playing a tape on The Midnight Special [a beloved Chicago folk music radio show on WFMT], a cassette, of Steve singing “City of New Orleans.”

From that night I had Goodman pictured in my mind as a tall, skinny banjo-playin’ guy with a little beard [laughs]. That’s who I thought was playing “City of New Orleans.” He was actually about all of 5’1”. He’d poke you in the chest when you talked to him like Edgar G. Robinson. [Laughter]

As a kid I used to play the open mics at his club Somebody Else’s Troubles, and he’d walk in and just barely clear the bar –

Right. But onstage he was ten-feet tall.

He could be a tough critic, too. Once he heard one of my songs and he said, “That’s good, but I could’ve written the whole thing in two lines.”

[Laughs] Yeah.

Would he criticize your songs?

Yeah. The first time Kristofferson introduced Bob Dylan to Steve and me – this was back in the Village in Carly Simon’s apartment, 1971 – my first record wasn’t coming out for a week. And Kristofferson said, “Come on over,” and gave us Carly’s address. Carly was opening for Kristofferson at the Bitter End. He said, “I got a surprise for you guys.” So we come over and we’re sitting in Carly’s place, and there’s a knock on the door and in walks Bob Dylan. At this time, Bob Dylan was not doing any shows. Yet. It was after the motorcycle accident, years after, in the early seventies. He had just written “George Jackson.” You familiar with that song? “Lord, Lord, they cut George Jackson down/Lord, Lord, they laid him in the ground.” 

“Your typical Sunday, which was not a typical day at all. It was always different. Lonelier than the other days…late Sunday night would always be a different time to me. I wanted to try to pinpoint that, so I chose a John Garfield movie.”

So we’re passing the guitar around. Kris sings one. I sing one. Bob takes the guitar and says he’d like to play something he just wrote, so he sings that. Goodman looks at him [laughs] and says, “That’s great, Bob. It’s no ‘Masters of War,’ though.” [Much laughter] Man, I’ll tell you. “It’s no ‘Masters of War,’”. [Laughs] And I sang “Far From Me,” and Dylan sang with me. He had an advance copy of my record that Jerry Wexler had sent him. And he already knew a couple of the songs. So he showed up at the Bitter End and played harmonica behind me on “Donald & Lydia” and “Far From Me.” It was like a dream.              

So, yeah, that’s Goodman criticizing. It wasn’t just your song.           

Another great song you wrote with previously untouched content is “Jesus, The Missing Years.”

I wrote that in a total state of inebriation. I was afraid to look at it for about a week. I knew I had written it, and I was totally surprised that it was as together as it was. I didn’t change too much at all. I think I’ve still got the original transcript, if you wanna call it that. With arrows here and there moving lines around.

On the original record I went all around town trying to find the best recording of a lightning bolt. So I could start to sing with a big clap of thunder. I bought nature albums [laughter]. With the sounds of rain and hurricane, till I finally found a clap of thunder. Put a bunch of echo on the voice just for the title where it goes, “Jesus, The Missing Years.” Then I play boom-boom-boom and go into this talking thing. I think it was mostly about Hank Williams’ “Luke the Drifter.” I was just trying to emulate that, though I knew Hank Williams would never talk about Jesus that way.           

You and Steve Goodman wrote the song “The 20th Century Is Almost Over” together –

Stevie actually had that. I thought it was a complete song. He just didn’t have enough verses. I wrote a couple of verses. In other words, it was his baby, and he wanted to cut me in on it. He wanted me to help him with it, and I said, “Here.” And came up with some fresh ideas. And next thing I know he’s in the studio and he’s got Pete Seeger singing. And it was the first time I had ever met Pete. He’s really something, man.     

I agree. Another unusual collaboration you did was with Phil Spector on “If You Don’t Want My Love.”

Right. The writer for the L.A. Times, Robert Hilburn, was trying to get together a book on Spector. He was interviewing him at length over a period of time. I came to town, and Hilburn was a big fan [of mine], and he would mention my name at the drop of a hat. I mean, if he was doing a Led Zeppelin review, he’d somehow fit my name into it, you know? I was amazed at how much press he’d give me.

I ran into him – I think it was when I was out there interviewing all those producers I told you about for Bruised Orange before I settled on Goodman. And I wasn’t talking to Spector about producing, but Hilburn told me he was going out to his house a lot, and said, “Would you like to come over? He likes your songs a lot, you know.”

I said yeah. He said, “He’s a big fan of ‘Donald & Lydia’,” and mentioned a couple of others. I said, “Yeah, I’d love to meet him.”Yeah, and you know, wow! He is out there. Met him a couple of times since then. And now this whole deal went down [Spector’s trials for the death of Lana Clarkson], and I don’t know, I’m surprised but I’m not.              

Did you see the gun?

Oh yeah. He had the gun. He always had it. You’d always see it before the end of the evening.           

How did you write a song together?

It happened on the way out the door. We’d been there for seven hours, jokin’, drinkin’. And by the way, when you go in the house, he’s got two bodyguards on his shoulder. It was just craziness, you know. This chick came down to say good night and he goes, “Who is the king of rock and roll?” And she said, “You are, Daddy, you are!” [laughs] I’ll never forget that.           

So I was leaving around four in the morning, and all of a sudden Phil sits down at the piano as I was getting my jacket on, and he hands me an electric guitar unplugged. And I sit down on the bench next to him. I played him “That’s The Way The World Goes Round,” and he really liked it. He said, “Let’s do this,” and he played the beginning notes of “If You Don’t Want My Love.” And we came up with the first couple lines and he insisted that we repeat them. Over and over. He said it would be very effective. And we took “That’s The Way The World Goes Round” and took the melody and turned it inside out. And used that as the basis of “If You Don’t Want My Love,” and he played it on piano and I just strummed back on the guitar, and we just wrote the thing in less than an hour. And that was on my way out the door. And as soon as he sat down and had a musical instrument, he was normal.That’s the way he was. He was just a plain old genius.

He’d just finished the Leonard Cohen album [Death of a Ladies Man]. And it hadn’t been released yet. He played it for me in his billiard room and turned the speakers up so high that the balls vibrated across the table. And this is the Leonard Cohen album! [Laughs]And I went back playing the song. Didn’t know I would do it for the record, but I played it for Goodman, and he said, “You oughta do that for the record. That’s great.” And I said, “But I don’t know if it’s done.” He said, “It’s done. Believe me. I’d tell ya if it wasn’t.”

So I cut it for Bruised Orange. Went back to his house after I cut the record to play it for him. Said he liked it. Said he would’ve produced it differently, but he liked it. [Laughs] I said, “You can take that up with Goodman sometime.” [Laughs]

Do you remember where “The Late John Garfield Blues” came from?

It was originally called, on paper, “The Late Sunday Evening Early Monday Morning Blues.”  There was a sort of movie that you’d see on Sunday night that you would not see the rest of the nights of the week. And I believe it was on WGN. They’d show these old black & white flicks. And a lot of my favorite ones were John Garfield movies.

I put the two together – the image of him and that kind of odd Sunday time, the Sunday funnies would be laying around and Parade magazine. Probably had a big dinner at some point.

Your typical Sunday, which was not a typical day at all. It was always different. Lonelier than the other days. And there was the feeling that you had to go to school the next day, or to work. So late Sunday night would always be a different time to me. I wanted to try to pinpoint that, so I chose a John Garfield movie, and I didn’t mention the movie at all, I just called it “The Late John Garfield Blues.” There’s an old Jimmy Rodgers melody-wise song that I was using. Just the chord change.  “Treasures Untold.” It’s a really pretty ballad that he wrote. I learned that song early on and I always wanted to use that G to the B7.

Do you have a favorite key?


Yeah, you play a lot in G.

I can fingerpick really good in G. [Laughs] I can pick “The Star Spangled Banner” in G. I can pick out just about anything I want in the key of G.

I’ve seen you play a lot in G but with a capo on.

I use the capo up and down the neck, and play in G quite a bit. I only get out of it out of sheer boredom.

Do you use the capo while writing the song or does that come later?

Usually later. When it’s more comfortable to sing in a higher or lower key.

“People say, `Gee, I didn’t think anybody would ever write about that particular emotion.’ And they tell you that you nailed it right on the head. That’s a really great feeling.

Do you feel different keys have different colors or moods?

Yeah. Definitely. It makes a big difference. After I had my throat surgery I had to drop the key on a lot of my older songs. And I was still singing them in the same key I wrote them in. My voice had changed anyway before the surgery. My voice was very nasal; my nose was a more comfortable place to sing out of than my throat. [Laughter] But my voice dropped quite a bit, and some of my songs, to me, just blossomed in the new key and I got to actually enjoy them as if they were brand new. Which was a really amazing thing. I had no idea changing the key would make such a big difference.

Your song “Donald and Lydia” is your only one I know of which is really about two characters with separate stories who you then bring together. Did that come together naturally or did you plot it out?

Well, like I say, my guide for the song was “Lonesome Death of Hattie Carol.” Just in terms of the character and what the character’s doing. And then the chorus could be a moral for the whole thing. I had the characters in my mind but I brought them together. Somewhere in boot camp I’d seen the character Donald. And in an army town where I was stationed, I think Louisiana, I’d seen Lydia.  And mostly they just formed together in my mind.

You’re a writer who has written about loneliness effectively –

Yeah. And the more I sing about it, the more I realize I’m not the only one. [Pause]  I think it’s great therapy to sing about the stuff that’s goin’ on inside you. And other people say, “Gee, I didn’t think anybody would ever write about that particular emotion.” And they tell you that you nailed it right on the head. That’s a really great feeling.

I think of your song “The Speed of the Sound of Loneliness,” which is kind of a later version of the same theme.

Yeah, that came out all at once. From a broken relationship I was in. I could not understand what went wrong and I had to explain to myself, and I did it through this song.  The next day I thought, Jesus, that’s beautiful. I didn’t recognize it at the time, it was just pouring out of me.

 Very cool title.

Yeah. Yeah, I really liked it. I guess it must have been a play on the words of “The Loneliest Long-Distance Runner.” Probably. I’m guessing. [Laughs] When it was all said and done, I don’t know where it came from, but I’m thinking that’s maybe that’s where I got the idea to use ‘loneliness’ like that. Cause it was a long title and kind of abstract, and I guess I’m attracted to stuff like that.

You’ve written a lot of songs out of heartbreak and turmoil. Can you write songs as well when you’re happy and things are going well?

Yeah, but usually when you’re happy, you don’t have time to write a song. Cause you’re enjoying your life. But when you’re not happy, you have all the time in the world to go and write a song.                                                                                                                                                                                                                                                                       

(Main Photo credit: Estelle Massry Photography)

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John Prine named Artist of the Year at the 2020 Americana Music Association Honors & Awards