"Eloquence" is the word that comes up often when peers and fans describe your music. What's your reaction to that, and where do you think this gift came from?
I didn't know I was a songwriter at first. I learned how to play the guitar from my older brother, and he taught me three chords and gave me a Carter Family record. I was into rock n' roll but my brother gave me a Carter Family and an Elizabeth Cotten record. He was into folk music. So I learned to play my guitar from those two records and what my brother taught me. As soon as I started trying to learn other people's songs, I would forget the lyrics and so I started making up my own words because it was easier. So that's what I was doing, just making up my own words for nobody in particular. And once it got pretty comfortable with three chords I learned a couple more and I started writing my own songs at 14. Just to impress girls. I never really thought I had a future in professional songwriting at all. I come from a western suburb of Chicago and I didn't know anybody who made records.
So did you impress the girls?
I did. And that's as far as I wanted to go.
But then… you go and get discovered by Kris Kristofferson.
I did, and Kris was hotter than a two-dollar pistol at the time. He had just put his first record out a year before I met him, and he was playing a club in Chicago called the Quiet Knight and my friend Steve Goodman, who was playing all the folk clubs with me, he was opening for Kris. Kris played four nights at the Quiet Knight and every night Steve Goodman tried to get Kris to come over and see his buddy across town. And Kris couldn't care less at the time. He was a pretty busy guy.
So you were doing your own gigging across town?
Yeah, not the club where Kris was playing. So the last night Goodman hounded him about coming over to see his buddy John, and Kris got in a cab and came over. It was a Sunday night, 2 in the morning, the chairs were on the tables, the waitresses were counting their tips and I was waiting for my paycheck. And Kris came in with two other people. We got four chairs down and I got on the stage right in front of him and sang about seven songs. And then he bought me a beer and asked if I could get back up there and sing those seven again and anything else I wrote.
Do you remember what you sang?
I sang "Sam Stone," "Hello in There," "Paradise," "Donald and Lydia," "Illegal Smile" -- most of the songs on my first record.
Yes, those are a lot of the songs that ended up on your first album, which came out only a year later I think?
It was the same year. It was really a Cinderella story, truly. Especially now that I've been in the business for so long and heard so many stories and told people my story. Eventually I went New York with Steve Goodman, and we got off the plane and looked in The Village Voice, and this was total coincidence, and Kris Kristofferson was playing The Bitter End, so we took out suitcases and guitars and went straight to down to The Bitter End. It was my very first time in New York City.
What was that timing, was it soon after you'd met Kris?
About four months after we met. So we get out of the cab and Kris and his band are walking from next door to do their second show at The Bitter End, and Kris says, "You guys are going up on stage for three songs apiece." All the people in the audience were either record company people or A&R people, and I sang three songs that night -- "Hello in There," "Sam Stone" and "Paradise," and Jerry Wexler was there and at 10am the next morning Jerry Wexler calls. I hadn't been in New York 24 hours.
Just an incredible story.
I like to tell young up-and-comers that luck has a good deal to do with it. Luck and timing. But when the luck and timing comes along, you've got to have the goods. You're only going to get that one chance, so you've got to have the goods right then and there.
And everything just took off from there. What is your songwriting process, and has it changed much through the years?
I think I know less now than I did back then about songwriting. With me there's no particular way. I just wait until a song comes along. When I'm co-writing, I use more of a craft approach to it because you're working with someone else. You can't just sit there and wait until the lightning strikes when you're co-writing. So that's the only difference. But right now on my own, I swear, every song I write on my own I think it's the last one. Because I just don't know if I can write another song. Sometimes I have to wait years, and sometimes it's only a day or a week until the next one comes.
What kinds of thoughts and/or experiences jumpstart a song nowadays?
Like right now, doing the interview, I'm driving over to get a haircut. If I'm doing something else, like driving, I find it opens up the right side of the brain to get the inspiration. But I have to be doing something. I was speaking with a young songwriter who I like a whole lot, Tyler Childers—he was in Australia with me—and he told me a story that made total sense to me. He hadn't written in a while and he said after he wrote his first record he was doing something in his garage with his toolbox and he spilled a bunch of ball bearings on the floor. And as soon as he got down on his knees and was picking those up, the side of his brain that writes songs kicked in. You have to kind of keep the other side busy to open up the side where inspiration comes in. I don't know about others, but that seems to work for me.
You mentioned co-writing. Which have been some of your most memorable experiences collaborating?
I resisted co-writing in my early career except with my buddy Steve Goodman. He was one of my earliest co-writers and that was just because we were such good buddies. When I got down to Nashville, I moved here in March of 1980, and down here anybody you bump into, one out of three of them is a songwriter. And so a lot of people who became my friends also happen to be songwriters so I couldn't help but write with them because I hang out with them. And I like to keep it that way rather than making an appointment with a stranger. This way, if you write with somebody that you like to hang out with then it's not a total waste if you don't write a song that day.
Who are some of your favorite songwriting friends?
Pat McLaughlin here in Nashville. He's a really great musician. He was out on the road with me for the last three years. He's been doing a lot of other things now but we still get together and every time we sit down it's like he finishes my sentences and reads my thoughts and vice versa. It's almost like a ping pong match. It goes back and forth, like we're reading each other's minds.
Your songs have been performed by so many artists through the years. Which covers stand out?
Bonnie Raitt doing "Angel from Montgomery." And Bette Midler and Joan Baez, both their versions of "Hello in There."
I've heard Bob Dylan considers you one of his favorite songwriters. A big compliment coming from someone who doesn't hand them out often. Who are your favorite songwriters?
Bob Dylan. Kristofferson. Gordon Lightfoot. Stevie Wonder. There's a bunch of them I really like. Townes Van Zandt. Guy Clark.
If you weren't talking to me in the car right now, what would you be listening to?
I'd be listening to country. I like the AM station down here, WSM, it plays old classic country, which is what I like. And rock n' roll has a really good station here, too, outside of town. They play a lot of alternative rock and country rock. I like the Stones, I like the Beatles. I was a big Elvis fan and I like folk music. I like the Carter Family, Gillian Welch. Stuff like that.
Is there a story behind one of your songs you'd like to share with us?
It's the song "Paradise," which has been covered by loads and loads of bluegrass bands. My father and mother are from a little town in Kentucky and I used to go there a lot as a kid in the '50s and '60s. I got drafted in the Army in the summer of '66, and my dad sent me an article he cut out of the paper. I remember him telling me they tore town down his hometown, the coal company did, they stripped out the whole area. I was just starting to write songs again when I got into the Army. I'd taken a break, and my dad had told me earlier he didn't think what I'd done were 'real' songs. I started writing songs again when I was over in Germany, so I wrote a song about his hometown, which I knew really well because I'd spent some summers there as a kid. I knew that if I wrote a song about him, he'd know I was a songwriter. He used to have me sing Hank Williams songs in our kitchen, so I tried to write a country song with him in it.
I think you convinced your father, and a whole lot of other people, that you were indeed a songwriter.
There's a story behind every one of the songs. That one was about a true story, so many of the other ones would just be inspirational. Like sometimes I'll take a character I know and I'll disguise them. I don't want someone to realize that they're in the song because they may not like the way the song ends.
What did your parents think about your musical career when it took off?
My father never played an instrument or sang, but he grew up listening to country music all day and all night. My mom used to sing while she was cooking, she never thought she had a singing voice but I always thought she had a pretty voice. They were really, really proud of me. I told my dad when I got the record contract. He was sitting on the front porch watching the cars go by and drinking his beer. And I told him they gave me $25,000 and a record contract. And he was real silent and then he looked over at me and he said, "Watch out for those F'in lawyers." I thought that was good advice.
What's different about writing at this stage of life vs. back in the Cinderella days?
Well, when I put this newest record out last year, a lot of people said I was writing songs about mortality. I think they just were thinking about my age. I didn't feel like I was writing songs about being older. There was that one song "When I Get to Heaven," and that's the one song they were talking about.
Do you feel older?
When I get up in the morning, I'm 9 years old between my ears. I'm not a 72-year-old man until I get in front of a mirror.
Your most recent album The Tree of Forgiveness, released last spring, was your first album of original music in 13 years. Are you writing again now?
I'm just starting to write for the next record. I'm hoping to put one out in 2021. I'm getting ready to do a record of my buddy Steve Goodman's songs. He died of leukemia in 1984, and I was waiting until I got a higher profile, which I have now, and thought I'd sing some of his songs and maybe get some people who never knew about him interested in him.
That's really lovely. So the next album won't be of your original songs?
No, that's another one. There will also be an original John Prine record coming.