Billionaires are rarely happy people. When the measure of your worth is based on how much you’re worth, there will always be someone with just a little more, making you feel just a little bit less. Jimmy Buffett was the exception to all of this. He was a billionaire who radiated happiness. He had the immense financial rewards of his talent and the business savvy of his wife, Jane. He surfed, bonefished, flew seaplanes, and pretty much lived the Parrothead life that he preached. Along the way, he had a charmed marriage, raised three kids, and was a New York Times best-selling author. Performers, by the very nature of their work, bring exponential joy to others. And Jimmy certainly did that. Here are a few remembrances from friends who knew the performer and the man himself. —Graydon Carter

TOM FRESTON

Tom Freston is a media-and-entertainment executive, a co-founder of MTV, and the board chair of the ONE Campaign, an anti-poverty organization

No one I knew had more friends than Jimmy Buffett. Some crossed over, but mostly he had separate categories: surfers, fishermen, entertainment-business honchos, writers, musicians, and, in a category of one, Warren Buffett.

Jimmy was a dear friend, and I was his foreign-travel partner in crime. We shared a taste for the faraway and enjoyed any adventure, especially ones with unexpected twists and turns. Once, we were almost kidnapped in the Sahara Desert and taken to Mauritania by some al-Qaeda dudes. Along came a nomad with a Bob Marley ringtone on his phone who partially saved us. But that’s a longer tale.

Buffett, Carey Lowell, and Tom Freston.

When we’d venture outside of North America or Europe, few people had heard of Jimmy Buffett. He could walk around like the rest of us complete unknowns. It was in these places that his urge to entertain was at its most primal. If he saw a stage, he wanted on it, even if the people on that stage had no idea who the hell he was. It seemed rude and intrusive, but the results were always the same. He overpowered all odds.

Thirteen years ago, Jimmy, his wife, Jane, and I visited Saigon. Vietnam was just going capitalist. We ran into a friend, Brian McNally, who was living there and planning to open a nightclub. As he dragged us to see the site, we passed through the teeming red-light district. At a bar called Club Sixteen, a quartet of drowsy Filipino guys in Beatles haircuts were playing cover songs on a stage that opened onto the street. We sat down and ordered beers. Jane was mortified to be sitting in such a place. “Fucking Jimmy!” she said, shaking her head. But Jimmy was jumping out of his skin, itching to get on that stage. He saw an opportunity—and he saw an extra guitar.

Buffett and friend in Key West, 1995.

After two songs, he tugged the bass player’s pants and asked to join in. The bass player tried to ignore him. Before the guy could even answer, Jimmy had strapped on that guitar, mumbled something to the Filipino Beatles, and launched into a searing version of Van Morrison’s “Brown Eyed Girl.” He owned it. The den of iniquity was electrified. Soon the entire street was jammed. Who was this singer?

If he saw a stage, he wanted on it, even if the people on that stage had no idea who the hell he was.

The song went on and on … for 15 minutes. I was almost peeing in my pants laughing. When it stopped, a skinny Chinese cat in a tuxedo got up and announced, “Big American rock star, ladies and gentlemen, big American rock star! Let’s hear it for him … Mr. Brown!! Let’s hear it for Mr. Brown!”

Jimmy weaseled his way onto stages throughout Africa. Before you knew it, he’d be strumming a guitar, his little white head bobbing up and down behind a thundering percussion section of towering Black men. He’d have that smile on. I knew he was thinking, Can you believe this shit?

At four a.m. in Bamako, Mali’s gritty capital city, the tables turned. We headed to a place called Hôtel Wassoulou. It had already been a long night of music and drinking. In Africa, the biggest stars often own their own clubs. Oumou Sangaré, Mali’s biggest female star, owned this one.

Oumou roamed the smoke-filled room with her microphone. She stopped at our table. She recognized Jimmy Buffett. She had the crowd implore him to get up: “It’s Jim-ME! … Monsieur Margaritaville! Do we want him to sing tonight?” Now, Jimmy was a man who knew his limits. He was on the other side of tipsy. Plus, the level of musicianship of these players was way over his head. But Oumou pulled him toward the stage. He looked as if he were marching to his execution. He would be humiliated at last.

Buffett performs at Jazz Fest in 2006, the first after Hurricane Katrina.

After a long huddle with the band, Jimmy spoke to the audience in French and started belting out “Who Do You Love?,” a song which, brilliantly, had no chord changes. It, too, went on and on. The audience leapt to their feet, cheering on the exuberant white interloper.

Jimmy later wrote in a magazine article that “Bo Diddley saved my life one night in Africa,” and that the song had been with him since the first day he heard it back in Mississippi. “[I was] just waiting for the right place and the right time to do its magic. ‘Thank you, Bo Diddley, thank you.’”

Jimmy could not help himself. The stage was always his greatest friend.

BONO

Bono is the lead singer of U2, a philanthropist, and the author of a memoir, Surrender: 40 Songs, One Story

In U2 we often find ourselves writing about feelings or places, lives or ideals we don’t yet occupy. Jimmy Buffett had the life we all would have loved to live. The adventurer buccaneer had one other talent and that was to turn his songs toward parable—he actually lived them!

MAUREEN DOWD

Maureen Dowd is a columnist at The New York Times and a Pulitzer Prize winner

Jimmy Buffett felt strongly about Donald Trump. He was a loyal Democrat and often did fundraising concerts for candidates. He was enormously relieved when Joe Biden got into the White House. But he never wanted anyone in his audience to feel unwelcome. He was not someone who had been lavished with a lot of awards, although artists from Bob Dylan to Paul McCartney admired his songs. Whatever hurt he felt about that he kept to himself, saying that the love from his audience was the best award. So, he wanted to respect different views among his fans.

Joe Biden and Buffett at a get-out-the-vote rally in Florida for Hillary Clinton in 2016.

I sent him a copy of Neil King’s book, American Ramble, earlier this year. It’s about healing from a bout with cancer by having an adventure, a walk from D.C. to New York. After he read it, Jimmy wrote to Neil, “Yes, I am in the C club too, and do I fucking believe in science or what?”

He became a billionaire by patenting vacation. He wanted people to enjoy themselves, dancing together and drinking margaritas and wearing parrot heads, especially as divisions deepened and the fault lines of our country pulled apart.

When he re-recorded the classic “Changes in Latitudes, Changes in Attitudes” with his “wingman” Mac McAnally, in Malibu in 2020, he wrote me that he was not putting in any politics or pandemic sadness. “We decided to not poke any beasts that were readily available, but just do a song that might summon up senses of humor that have been exercised very little in the last four years and take us into 2021 and hopefully better days with a laugh,” he said. “As Lord Buckley used to say, ‘Terror is the absence of humor.’”

He was enormously relieved when Joe Biden got into the White House.

After Trump lost in 2020, Jimmy was blunt. He said he hoped Trump would wallow in his own dirt and be as uncomfortable every day for the rest of his life as he has made many Americans. With an epithet directed at Trump, he added: “Let’s get fun back on TV and everywhere else.”

In the last few years, as he fought Merkel-cell cancer—a rare and aggressive form of skin cancer—he leaned into his two rules of rock ’n’ roll: “Never forget to duck” and “Never forget it could go to hell at any minute.”

He was upbeat and fiercely kept making his way back to the stage. Over July 4, he wrote me: “I am doing ok, and actually did a small ‘Pop Up’ show with Mac over the weekend in Newport. I was the opening act, and a bit nervous and shaky on the lyrics of the first couple of songs, as I was checking out the crowd going crazy. Hadn’t heard that in a while. Mac coached me back to the lyrics of ‘Changes’ and we were off and running. It felt great to do a show.”

While he was recuperating between infusions at Sag Harbor this summer, surrounded by his wife, Janie, his kids, his dogs, and his band, I sent him a bunch of old 45s, including Jean Shepard, Johnny Cash, Conway Twitty, Waylon Jennings, Glen Campbell, George Jones, Roger Miller, and Porter Wagoner duets with Dolly Parton.

“I loved the stack of 45s, and I have a turntable with an adapter that will play the 45s,” he wrote me. “But now I am looking for a juke box I can put them in.” He sent me a preliminary cut of a new album, instructing: “So, attached here is a link to the sequence of the songs on the new album, that we will start streaming in about 10 days. I am too old-school, thinking that people listen to albums all the way thru these days. But sequence and moving tempo and feeling for an album is a habit I can’t shake. So, my suggestion is to listen to them in the order they appear, and take a drive out to a beach somewhere on the Chesapeake, and see how the songs sound.”

Buffett in the late 70s.

He added, “I am headed for a new round of the latest treatment procedures for Merkel at MD Anderson in Houston, which looks very promising for long term treatment. Hope to make it to Merriweather sometime in the late summer for a real show. I will keep you posted.”

He didn’t make it to Merriweather. But his joyful music and the warmth of his charm will live on forever. One of Jimmy’s favorite expressions was “the whole enchilada,” and, boy, was he that.

Neil King

Neil King is a former Wall Street Journal correspondent and the author of American Ramble: A Walk of Memory and Renewal

Oddly, we’d become remote cancer comrades over the past year—me the so-called survivor and him in the thick of it, but ever humorous and upbeat and cheerful.

I sent him a copy of my book, and then another when he lost it on a beach or in a hotel somewhere, and then finally a third, just a few weeks ago. “I am 3/4 the way thru when it disappeared,” he wrote. “I would love to finish it for knowledge and inspiration centered around your experiences.”

Me, giving inspiration to Jimmy Buffett. I went straight to the post office and shot him another copy.

In return, he sent me a digital link to his unreleased album, all 14 rollicking and wry and soulful tunes, his vocals strong, backed up by a stellar set of ace musicians. “Send me some input on what were ur favorites and why,” he ordered. Me, giving musical advice to Jimmy Buffett.

Last fall, soon after we’d connected, he sent a note expressing his anger at a Washington Post column that equated his concerts to a MAGA-fest. “What do you think I should do?” he asked. Me, being asked to give P.R. advice to a guy who had amassed an empire and a fortune on knowing how and when to do the right thing.

He knew what was what, and so much more.

“Truth is,” he wrote back after I passed along some basic advice, “probably 40% of our fan base are Trumpers of some sort. I always thought about how the warring tribes in the Sahara, and Union and Confederate soldiers in the Civil war, usually had to rest and water at the same oasis, then they went back to fighting. I always felt what we provide was that Oasis, which is why I never took politics to the stages, when people paid good money to be simply entertained.”

CARL HULSE

Carl Hulse is the chief Washington correspondent at The New York Times

Nobody personified sun-soaked, summer days at the beach, on the water, or at the tiki bar like Jimmy, even during the long dark days of winter—boat drinks, anyone? Jimmy didn’t just capture the carefree tropical Zeitgeist, he invented it and practically single-handedly made Key West into the destination it is today.

Buffett sings with U.S. Embassy employees before a Rolling Stones concert in Cuba.

Jimmy knew he had hit the jackpot, rising from a scruffy troubadour on Duval Street to a musical legend and, along with his business associates, a successful entrepreneur and author, and it showed. There was no pretense or privilege about him. He really enjoyed being Jimmy Buffett. Once at a dinner in downtown Washington, a drunk younger patron sidled up to the table and accused him of NOT being Jimmy Buffett. He happily pulled out his driver’s license to show her that indeed he was.

LINDA WELLS

Linda Wells is the Editor at AIR MAIL LOOK and the founder of Allure

When Jane Buffett decided her husband’s career needed a jolt, she did what she always did the way she always did it: no fanfare, no drama. Just action. As the opening act for the Eagles in the mid-1970s, Jimmy knew his prospects were looking up. But maybe not up enough. One night, as the Eagles played Madison Square Garden, Jane high-heeled her way over to a limousine parked backstage.

Tap, tap, tap. The man in the back seat rolled down the window.

“A beautiful young woman got into the car and said with that Southern drawl, ‘Hi, I’m Jane Buffett, and I need you to manage my husband,’” Irving Azoff, the rock manager and music executive, tells me. “She wanted to steer him away from Nashville and country.” And up things soared from there.

Buffett sails with his wife, Jane.

Behind every great man is a great woman and all that. And sometimes in front of that great man is a great woman bushwhacking a path for him, knocking on opportunity’s limousine door, and shining the bright lights his way. That’s the great Jane Slagsvol Buffett, wife of the great Jimmy, who was as instrumental to his success as his Martin guitar.

They met in Key West when Jane, on spring break, saw a fellow wearing a cowboy hat, boots, and a pile of turquoise jewelry. It was the early 70s, but still, no one dressed quite like that. “Oh, that’s the local troubadour,” someone told her; he was playing in a bar that very night. She slipped on a long pink dress and, as she walked into the bar, Jimmy stared straight at her from the stage and broke into “Say hey, good lookin’ - what you got cookin’?” End of story.

Or beginning. Several years after that meeting, Jane told Jimmy, determining their future as she tended to do, “I’m going to be your wife.” They married in Aspen with the Eagles as wedding band. At the after-party, Hunter S. Thompson threw Jane over his shoulder and dropped her down next to her passed-out husband in the marital bed. If Hunter Thompson is the sober person in the room, you know it’s quite a party.

“A beautiful young woman got into the car and said with that Southern drawl, ‘Hi, I’m Jane Buffett, and I need you to manage my husband.’”

Thanks to Jimmy’s sunny, breezy talent and Azoff’s muscle, there were Rolling Stones covers, arena shows, and the handsome sums that poured in with them. But it was the merchandising and licensing of that boozy, carefree spirit that made Margaritaville into a business phenomenon, and Jane had her hand in that too. Jane saw the T-shirt sales here, the restaurant income and beer sponsorship there, and thought there had to be a way to connect the pieces. She met a finance executive who had interests in fast-food chains and beverage brands and thought, We need someone like that. She invited the executive to a meeting at the Buffetts’ Palm Beach house, but Jimmy said he’d rather take a nap. Jane roused him, and they soon turned that endless summer feeling into an empire.

“Margaritaville” the song was all Jimmy. Margaritaville the multi-billion-dollar conglomerate “wouldn’t exist without her,” says Azoff.

They were a team, Jimmy and Jane. Married for 46 years with a 5-year break for, as she calls it, bad behavior. After they reunited—which was after she realized every other man she met was “the same wolf in a different sheep’s clothing”—they developed a new respect for each other. She called him “dude”; he called her “goddess.”

Jane and I sealed our friendship at a birthday party in London. We’ve traveled the globe together, sometimes with Jimmy, sometimes without. When they were apart, they’d call each other before bed. “Hey, goddess,” I’d hear from the next room. “Hey, dude.” They’d tell stories, they’d put the dogs on FaceTime, and he’d report on the evening’s performance, eager for her approval until one or the other was nearly asleep. Their love story was unconventional, and it was real.

Buffett flies high in Honolulu.

Jimmy was perfectly content spending his evenings with takeout pizza and a telescope pointed at the stars. But Jane’s illumination was candlelight, and she drew people to their dinners in Sag Harbor, Beverly Hills, St. Barth’s, and New York, which she choreographed like Balanchine. Everyone felt safe enough to get a little loose. She’s Gertrude Stein with rock stars. Sue Mengers without the cigarettes.

It was Jimmy who took the stage and bathed in all the love that he sent out and the love that ricocheted back. It was Jimmy who won over the cynics with his sheer goodness and joy. And right there next to him, and sometimes in front of him, was Jane.