Like all artists of any note, Jimmy Buffett had more than his share of paradoxes: He was a laid-back lover of the tropics who became a business titan, a writer of heartbreaking story-songs who founded a tribe of Parrotheads. In our 2020 interview, posted here for the first time, Buffett puzzled through the triumphs and contradictions of his life in music, looked back at some of his greatest songs, and more. To hear even more of the conversation, check out the new episode of Rolling Stone Music Now here at the podcast provider of your choice, listen on Apple Podcasts or Spotify, or just press play below.
How has your songwriting process changed since, say, the early Seventies? Obviously, you use collaborators more now, for one thing.
In the beginning, I didn’t co-write with anybody because I didn’t know anybody else. [Laughs.] Nobody was really around, and few people were listening. When I got to Key West the very first time, I fell in love with it and moved there. I’d had five bad years in Nashville, but I was still writing. So I came to Key West with a little bit of luggage and a lot of songs. Being there, soaking up the cultural aspects from pirate days to the writers to the tolerant lifestyle the island had, affected me. There was the Navy, a gay community, hippies; I just fell right into it.
When you think about what you put out between ’73 and ’74 alone, it’s crazy. If you could go back and tell that guy from 1973 all the things that have happened to you since, what would he make of it?
I was on a quest. I think he’d be very happy that we made it. [Laughs.] When you start out, you have to commit to this. It’s not a part-time job. In those days, the ratio of success was minuscule. There’s a lot of wreckage on the road to success.
You have a whole different part of your life, this huge successful business that you run. When you go back to writing songs, does that feel like an entirely different part of yourself, or is it somehow all one thing in your head?
It’s interesting because, yeah, sometimes I do have to ask myself, “Hey, how lucky was I to figure this out?” Most of the business that comes along with performers was always, “As an artist, you don’t need to worry about that stuff. We’ll take care of that.” Talent was a very disposable commodity. If you had someone with a drug problem, you’d look for a younger person [to replace them]. There wasn’t a lot of help coming from your employer or record companies.
I was lucky enough to find work when I had no job and couldn’t play. I was living in Nashville at the time, in the late Sixties. I had to find some kind of work, and ironically, there weren’t many places downtown where you could get a job playing live music. I’d just come off two and a half years working on Bourbon Street. I was a good street performer, but couldn’t find a job. So, I answered an ad in the Nashville Banner that said, “Writer wanted, journalism degree needed.” I thought, “Aha, I have one.” I answered the ad, and it was for Billboard magazine.
From being turned away by every publisher at every door in Nashville when I was trying to get songs written, suddenly, they were sending me free records. I was doing reviews and covering concerts. I liked it, but I couldn’t give anyone a bad review because I knew what it took to perform. During that period, I learned what the music business really was. And to a large extent, it’s still stacked against you as a performer unless you take command of your own situation.
So when it came to my career, I wanted to take care of business. When I first started, they took everything away. They’d say, “You want a record deal? Well, you can keep your publishing, but you won’t have a record deal.”
Through that gauntlet of experiences, I knew I wasn’t that good a guitar player or singer, but I could perform well on stage. That was my go-to while trying to create other opportunities. I wanted to be a working musician, playing on stage. So, during that whole process, I started thinking, “Why would I rent a piano at the price promoters charge when I could buy one and pay it off in 10 shows?” I thought about building my own bus and renting it to others when I wasn’t using it. Those ideas came from being raised in a shipbuilding family. I was thinking about ways to make performing easier and less expensive. It all started there.
You gave a commencement address at the University of Miami where you talked about a moment when you had to make it through a show hungover. You made it through the show, but in your mind, you knew you didn’t do the best you possibly could, and that was a big turning point for you. What happened there?
Yeah, it scared me to death. ‘Cause you think you’re bulletproof at that age, in that time, and you’re in rock & roll. Drugs and sex, everything was around and you don’t think about it, but there’s that thought process. For me, at that point, I didn’t want to make my family ashamed of me. That was a strong [motivator] for making that change in my life at that time.
I’d worked so hard and I didn’t want to be stupid about it. I feel lucky to have made some kind of right decision at the right time. But again, I’ve done it and I’m not proud of it, and I know other people can do it. And they call it a “take the money and run” show. It’s where you may not be feeling your best and you know that you can get away with something and the audience won’t know it, because they’re so happy to be there anyway. I felt terrible when those things happened. I never wanted to do another one.
I’ve always heard the melancholy in “Margaritaville.” It’s fascinating that a song with that obvious melancholy not only became a huge hit but also the linchpin of a whole brand of escapism. How do you reconcile that in your own mind?
I never thought about it when I wrote it. I started in Austin, Texas, in a bar. A friend of mine put me on a plane to go back to Key West, and I finished it there. I played it in the bar; people liked it. But I go back to what Ry Cooder once said: “You never know what the public’s going to buy.”
The interesting thing, to your point, is that when we did the musical and the play, it was presented as a melancholy song there. But the theme of Mardi Gras is “folly chasing death,” so you gotta have fun to keep the devil away. I loved the way they did it in the play, and I’ve never done it that way, but I sure liked listening to it that way.
When you first heard years ago that Bob Dylan had covered “A Pirate Looks at Forty,” what was your reaction to that?
I was thrilled about it. Unbelievable. And then years later I met Dylan in St. Barts when he sailed in on his boat, and I spent a day with him on his boat. I was walking through the harbor and I was looking in the window of the marine supply store, and I heard this voice say, “Hey Jimmy, that’s a nice-looking pair of shoes, isn’t it?” And I looked around and went, that’s Bob Dylan. So he invited me out on the boat and we spent all day together there. We sat there and talked and got stoned all day long.
But then later I was in Paris doing something. I think it was when Dylan was with [Tom] Petty. I went to see the show and I knew Jim Callahan, the security guy, and he said, yeah, “Bob’s been looking for you. He wants to see you.” And I’m thinking, man, we have a bond here. And I go backstage and Dylan was sitting there eating, had his gloves and his hoodie on. And I said, I went, “Bob, how you doing?”
He went, “Eeeeeh.” He never said a word. I sat there the whole time. I ate my meal. I said “Have a good show. See you later.” And I haven’t seen him since. [Laughs.]
I think some people who have had odd encounters like that with Dylan theorized that maybe he wasn’t wearing his glasses. Maybe that could have been it.
I never thought of that!. He didn’t look up much, I remember that.
Does it ever feel like your business and touring success overshadow your songwriting in people’s minds?
It doesn’t, but, it amazes me now that I go back and look at the volume of how much is there, because you made an album a year ’cause they wanted an album a year. We weren’t big hitmakers, but we drew people. Somebody said once that we were like Deadheads with credit cards. And every now and then, I could slip something in like “He Went to Paris,” one of my favorite songs I wrote. And yeah, the songwriting probably gets overlooked sometimes, but I don’t mind. I’ve had a great run and I’m enjoying it, and I’m not telling people what to listen to.
When was the last time you got to be the other Jimmy Buffett and spend some time on a boat for a couple days, or be on the beach for a few days? Do you get to go into that mode still?
Like, yesterday? [Laughs.] Yeah. I was paddleboardin’ yesterday.
I love that.
And I’m going now. When I finish this interview, hey, there’s a nice little wave out there, and I’m gonna go surf.
On your new album you sing “live like it’s your last day,” and I guess I was wondering whether you think that’s actually good advice or not.
When you’ve had a couple close calls, like an airplane crash and a stage dive, you think you’re probably living on borrowed time. I tend to live like it’s my last day — you never know. At 73, we’re not getting any younger, is one thing. We’re losing a lot of friends, and it’s a constant progression towards what’s there.
And Jimmy, when you do leave us, how would you like to be remembered? What would you like people to say about you?
I’d say “He had a good time and made a lot of people happy” would be good. Yeah, that’d be good.
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