Although they both established themselves as leading summer-shed troubadours of the Seventies, Jimmy Buffett and James Taylor seemed to live in different parts of a harbor: Buffett the effusive showman, Taylor the introspective loner. In fact, the two had more in common than anyone would have expected. Both were sailors, and both (as Buffett joked in a recent tribute to Taylor) dealt with early fame, receding hairlines and getting healthy in later life. The two shared stages together and collaborated in the studio on a few of each other’s records.

As Taylor tells Rolling Stone, the two were in touch regularly until last year, when Buffett’s health issues became more pronounced; he died on Sept. 1 at age 76. “I was aware that he was sick and that he was fighting and struggling with it,” Taylor says. “I sent him some emails. I didn’t expect him to respond, but I wanted to be there for him.” Buffett’s private death was, Taylor thinks, also of a piece with his buoyant image and approach to music and performance. “He didn’t burden the rest of us,” Taylor says. “He wasn’t going to bring us down.” Here, Taylor remembers his friend of five decades.

Jimmy didn’t have any illusions about who he was and what he was doing. He made fun of himself and he made fun of the institution of celebrity. His eyes were always open. And yet it was always celebratory and joyful. Sometimes melancholy, it’s true — songs about compromise, tarnished dreams, stuff like that.

But you can’t think about the guy without smiling. You didn’t begrudge any of him any of his success because he deserved it all. He won it and had a sense of ease, inclusiveness and generosity. The main thing he shared with us was his joy of being alive and being himself. It was a gift to be around him, and it was delightful to witness that life. He had an immense amount of positive energy.

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There’s a sailing community, which is how I first became aware of him. For sailors and boat people I knew, in the Caribbean and on Martha’s Vineyard and on Long Island, he was a favorite, so I was aware of him before I met him. The first time we met, we took sail on a boat out of the Vineyard back in the early Seventies. A lot of his people, and mine as well, came from or made the living on the sea. We both were sort of brought up in it, so we had a lot in common. He liked single-hand sailing [sailing without a crew]. He liked to sail alone on a sloop, and he loved to build and design boats. He was a competent captain. I can take my turn at the helm and hold the course for an evening or for a watch. But you got the feeling as though Jimmy could direct the whole enterprise.

I always liked “Sending the Old Man Home.” I loved that he invoked the war in the Pacific in that song. I love “Come Monday,” which is great. I love the hits: “Volcano,” “Why Don’t We Get Drunk.” I love “Margaritaville.” There was a reason that was a hit. It was like a vacation to listen to that song. But at the same time, it exposed itself and gave you a hint of the dirty underside — the hangover. 

In 1979, my brothers Hugh and Alex and I went down to Montserrat, when Jimmy was recording Volcano, to do some backgrounds on a number of songs. I can’t remember much of the trip because it was a bacchanal. It was a pretty abandoned time. There were incidents. There was a sense about him that it was liberty hall and that he wanted to party on the edge. In New York there was many a soiree, many a cocktail. We could be pretty well lubricated. But Jimmy always stayed in control of the situation. You always felt you were in good hands, like he wouldn’t let you get into terrible trouble.

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Jimmy was an excellent businessman, but only because he couldn’t let it pass. He had to say, “Now, this can be done better,” or “This is a great project, let’s do this,” or “This will be a great book,” or “This is an excellent beer, but you could market it better.” He could apply himself to so many things, from aircraft to restaurants to hotels to movie projects and Broadway musicals.  

I don’t know if it’s apocryphal or not. But there’s famous story that, at one point, he was negotiating about a string of gigs all by the same promoter. I never asked him about it. But he’s rumored to have said, “Well, how about this? How about you guys take everything, and I’ll just take the proceeds from the bar?” Basically he was letting them know that they could give him 110% of what the ticket revenues were and they’d still be making a fortune off that. It was his way of letting them know, “I know what your income streams are. Don’t talk to me about giving me this crumb or that crumb or this piece of the pie.” It was so refreshing. It was his way of letting them know that he knew what was on the table. I’ve always loved the story.

People describe him as a lord of life, somewhere between Falstaff and the pirate Jean Lafitte. I feel as though he invented his own character, but that character was not very different from who he was. He didn’t concoct this fantastic person. He was who he was and who he presented himself as. He was sly and could be wicked, but there wasn’t a mean bone in his body, and he didn’t have that maudlin sort of hippie thing going.

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We go shopping in the popular culture for our own mythology, and we assemble our own character and channel people who we choose to represent us in a way. And he was a very valuable element of that thing we do. Being in his presence or being in the audience or listening to his music, it was like a break. You got to channel him in a way, and it was very compelling.

He founded an amazing tribe, the Parrotheads, that identified with him and was so inclusive. The people who loved him, loved him. My favorite story about a Parrothead is when Jimmy was wakesurfing one day–you have a surfboard and make your wave and surf it behind a boat. He was trying to catch a wave from a tanker, a big freighter. Jimmy somehow got the captain’s his name from the Coast Guard–maybe from his computer, because you can track marine traffic on your cell phone if you have the right app. He got in touch with the captain of the boat, and the guy changed his course and altered his speed to make the perfect wave for Jimmy to ride behind this freighter The captain was a Parrothead. It’s the perfect Jimmy Buffett story.

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