Jimmy Buffett Does Not Live the Jimmy Buffett Lifestyle

Jimmy Buffett awoke one morning last year in one of his many homes — he can’t remember which one, there are a lot of them — and a panic gripped him in his throat. His new Broadway musical, “Escape to Margaritaville,” was coming along nicely, but something was off.

It wasn’t the music — they’d been careful to include a finely titrated playlist of crowd pleasers. It wasn’t the book — the TV writers Greg Garcia (“My Name Is Earl,” “Raising Hope”) and Mike O’Malley (“Shameless”) managed to strike a balance of goofy, accessible romantic comedy and some deep cuts for the Parrotheads, as his fans are called. It wasn’t the casting, either; Paul Alexander Nolan is a compelling early-Buffett avatar as Tully Mars, a dreamy bar singer at a rundown Caribbean hotel called Margaritaville. And he was happy with the direction of Christopher Ashley, off a best direction Tony for “Come From Away.”

So what could it be? The writers were refining the characters and their motivations and he felt pretty good about that. The producers were taking great care with the show experience as well; they had decided to deluge the audience with beach balls at the end, which Mr. Buffett thought would be fun and memorable.

But it wasn’t that, either. He searched his mind and his heart and still, nothing. In the shadow of the early morning light across his bedroom in either Palm Beach or St. Barts or Sag Harbor or Los Angeles or Waikiki or New York, Mr. Buffett realized he needed to find the answer.

It hit him like a thunderbolt. It was Mr. Nolan. Mr. Nolan had just the right vibe. He could do the laid-back thing well; his singing is strong and contemporary. But there is a fatal flaw about him: He wasn’t tan.

“He’s Canadian,” Mr. Buffett said. Meaning, I guess, that Mr. Nolan maybe doesn’t know about tans? “Get to a tanning salon,” Mr. Buffett told Mr. Nolan. How could you have a bar singer beach bum in the Caribbean who wasn’t tan? “To me, it’s essential to the part. Tourists in Margaritaville are white and turn red. You need to be tan.” Mr. Nolan agreed and relief coursed through Mr. Buffett’s body. Phew. That was close.

In December, Mr. Buffett was still looking to make the show an even more authentic testament to the lifestyle he created and the escapism he knows his fans want. Previews were to begin at the Marquis Theater on Feb. 16. The show’s pre-Broadway runs in San Diego, New Orleans, Houston and Chicago had been well-received, but he still had concerns. He wanted to figure out another song to add to the mix in the show, but every time he tried to remember what it was really like to be a Tully Mars of the world, he blanked.

He called up his sound guy, who told him he was headed out on a fishing trip. “You’re not going fishing,” Mr. Buffett told him. Mr. Buffett realized that in order to remember his time as Tully Mars, he had to become Tully Mars again.

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Mr. Buffett hasn’t stopped touring in his nearly half-century as a performer, but it had been a long time since he did a last-minute set at a bar. He had to get on a stage with a pickup band like in the old days and really get back into the original iteration of Jimmy Buffett.

That night, he went to the original Margaritaville bar in Key West, which he opened in the mid-1980s, unannounced, and played a three-and-a-half-hour set. He told stories between songs. He kept the audience active. It felt good to be back there, remembering who he once was.

Because that, in a coconut shell, was the problem. Jimmy Buffett is not really Jimmy Buffett anymore. He hasn’t been for a while. Jimmy Buffett — the nibbling on sponge cake, watching the sun bake, getting drunk and screwing, it’s 5 o’clock somewhere Jimmy Buffett — has been replaced with a well-preserved businessman who is leveraging the Jimmy Buffett of yore in order to keep the Jimmy Buffett of now in the manner to which the old Jimmy Buffett never dreamed he could become accustomed. And therein lies the Margaritaville® Mesquite BBQ Rub: The more successful you become at selling the Jimmy Buffett lifestyle, the less you are seen as believably living the Jimmy Buffett lifestyle.

Who is to say when the chasm between the Jimmy Buffetts became so deep? Probably it was around the first time he put the Margaritaville name on a salt shaker-shaped pool raft labeled “Lost Shaker of Salt.” Or went all-in on a brand partnership to sell a $499.99 Tahiti™ Frozen Concoction Maker®. Or when he signed off on the emblazonment of “I’m the Woman to Blame” across a Tervis tumbler. Sometime around then, Jimmy Buffett entered a point of no return where the lifestyle of the erstwhile Jimmy Buffett became so distant and unrecognizable to the new Jimmy Buffett that he understood there could be a problem in the making. “The glue that holds this thing together is authenticity,” he told me on the 35th floor of the Mandarin Oriental hotel, where he eats breakfast when he’s in New York. “People can smell it if it isn’t real.”

IN 1979, Mr. Buffett showed up literally years late to a Rolling Stone interview, barefoot, in St. Barts, where he was living off a boat. On the first day we met, back in October, in New Orleans, the morning after opening night of the musical, he showed up on time at 9 a.m. Now he is surrounded by publicists and producers and a bodyguard. Now he has a boat but also another boat and some airplanes. Now he wears shoes just about whenever you’re supposed to.

Mr. Buffett and I both saw “Escape to Margaritaville” in New Orleans on Oct. 28, which is a day that fans have long since designated as Parrothead Day, though Mr. Buffett doesn’t know why. In the audience, fans wore feathers on their heads. When they sang along, it was in a unified hum, reminding Mr. Buffett of the recitation of prayers in church during his altar boy days.

After the show, there had been a big party where Mr. Buffett D.J.’ed alongside the movie producer Frank Marshall, who is his friend and one of the show’s creators. He had a tequila on the rocks and “a lot of water.” He’s 71, a married father of three adult children. He only occasionally drinks margaritas these days. “I don’t do sugar anymore,” he said. “No sugar and no carbs. Except on Sunday.” He doesn’t smoke pot anymore, either. Now he vapes oils, only sometimes after work.

“Escape to Margaritaville” will be Mr. Buffett’s first Broadway musical, but not his first musical. In 1997, he and his friend the novelist Herman Wouk, of all people, wrote one based on Mr. Wouk’s 1965 novel, “Don’t Stop the Carnival.” It’s not as unlikely a marriage as it sounds; the book was about a Manhattan press agent having a midlife crisis who leaves New York for the Caribbean. It played Miami; The Orlando Sentinel said that it suffered from “flat characters and weak songwriting.” After a brief run there, they took it to the Atlantis resort in the Bahamas, where it played until 2001. It never made it to Broadway. There were some investors who wanted it to, but they told Mr. Buffett that he would have to lose the dead weight — the dead weight being the Pulitzer Prize-winning Mr. Wouk. Mr. Buffett politely declined.

Other Broadway offers came and went. In the 1990s, Jimmy Nederlander Sr. and Jr., the theater impresarios, took him to the Polo Lounge in Beverly Hills to tempt him with a one-man show a little like the one Bruce Springsteen is currently starring in. But it didn’t seem economical. The theater needed to hire way too many crew members, and Mr. Buffett did the math and realized he’d lose money, compared with his take on the road. “Can we do two weeks instead?” he asked. His mother would have been thrilled to see him on Broadway. Alas, the answer was no.

When a potential jukebox musical was raised in 2014, he liked the idea. He talked to Mr. Marshall, and said they should partner up and do it right. “I don’t want another person’s version of me,” he told Mr. Marshall. “Find me some good writers who are basically Parrotheads who have been raised on this music because that’s important.” Mr. Buffett found that with Mr. Garcia and Mr. O’Malley, both of whom have written great and believable slackers. Tully is the kind of affable yutz that Mr. Garcia, in particular, writes best. But perhaps the inspiration for Mr. Garcia’s previous affable bums had always been the old Jimmy Buffett: the kind of ne’er do well who grapples with living a life of purpose while not wanting to work very hard.

Mr. Buffett came into the national imagination in the 1970s, just in time to become a counterpoint to what would end up being called the Yuppie generation. What if you didn’t work that hard?, he dared to ask. What if your ambition was not for success or money but for the in-betweens: the vacations, the frozen cocktail and joint in the evening? His emphasis was on the essentially Buffettian notion that we’d all spend our lives on the beach splayed out on a towel, our lips caked with salt, if we could. “I don’t know anyone who wouldn’t spend a week on the beach,” he said. In his songs, Mr. Buffett imagined himself as a pirate, always plundering toward treasure. The treasure wasn’t wealth, though; the treasure was a destination; it was the ville in Margaritaville.

If Jimmy Buffett was a Jimmy Buffett kind of guy, these thoughts would have been incidental, thought up in a hammock then lost to memory the way the best boozy thoughts always are. But he’d taken a business class when he was in college studying journalism, and it stuck with him. The class covered supply and demand and goods and services. From the stage, looking out over the growing number of people wearing parrot headgear, he realized there was demand. He had supply. He could find the goods and services.

He had learned about the music business after college, when he wrote for Billboard magazine. There he saw how poorly the music industry took care of its artists. “It was indentured servitude, and it still is,” he said. He tried to stand up to the record companies, but it was impossible. He signed with MCA Records (now Universal). He wanted to keep his publishing rights, but the label wouldn’t give him a record deal unless it owned everything. What choice did he have, then? “If you apply supply and demand, there’s always a supply of talent who’s willing to do anything if you aren’t,” he said.

One day he realized that even if you were the supply, you could also be the supply chain. “It’s up to you to figure out how to take advantage or to manage whatever you’re going to do,” he said. “Margaritaville” was a hit in 1977. But more important, on that day, Margaritaville® was born.

He established Mailboat Records, his record label, in 1999. He went from making $2.20 per album to making $6 an album, he told me. He built his own tour buses, because it costs five times more to rent equipment than to own it yourself. He then rented out that equipment to other acts. And he took charge of his merchandise. He didn’t do it because he was greedy. He did it because he could do it better than the people who were ripping him off with concert T-shirts that spelled his name as Buffet.

He sold his fans quality, spell-checked T-shirts. He played clubs all over the country, but it was the crowds in landlocked areas that seemed to love him most. In Pittsburgh, he and his Coral Reefer band mates noticed that fans had started wearing Hawaiian shirts, just like they did, to the shows. One night, in Cincinnati, his bass player Timothy B. Schmit (also of the Eagles) likened them to Deadheads, the way Grateful Dead fans would follow that band. And so they were christened Parrotheads, just as a joke, but then fans began to wear feathers and beak masks to shows. “In their minds they wanted to go to the ocean,” he said. He understood he was bringing the ocean to them. He was no longer just a singer. Now he was a guru.

So how could he serve his acolytes better? What could he do to make sure that even when he left town they could still have the island getaway they so longed for?

Well, what if on your way to your burdensome job, you could listen to Mr. Buffett and the musicians he endorses? You could be stuck in traffic and listening to his SiriusXM Radio Margaritaville station. After work, you can bring Caribbean flavor to your kitchen with Margaritaville® Jammin’ Jerk Shrimp or Calypso Coconut Shrimp, both skillet-ready in minutes. Relax afterward by mixing up a batch of Margaritaville® Margarita Mix, in lime or mango flavors, because 9 a.m. will come soon enough.

Finally, it’s Friday! No more working for the man! So crack open a LandShark® Lager, manufactured by Anheuser-Busch under the name of Margaritaville Brewing Company.

Calendar pages fly off the wall, and at long last it’s time for vacation. There are six different Norwegian Cruise Line ships floating around that host the restaurants Margaritaville at Sea, 5 o’Clock Somewhere Bar and LandShark® Bar & Grill. Not seafaring? There are 11 Margaritaville® hotels, some of which have casinos. (The one I stayed at in Pensacola Beach did not, but it did have a clock that is stuck at 5.) When you check in, you are given a lanyard to carry around your room card for when you get too drunk to find it — there it is, right around your neck.

You blow out birthday candles, one more every year, and wonder what it’s all for. One day your cardiologist says to maybe ease up on all those cheeseburgers, and you’re just about done working for the man. Well, if you’re “55 and better,” you can move into Latitude Margaritaville®, an adult-living community in partnership with Minto which will be opening in Daytona Beach next year. Life could be like a never-ending stay in Margaritaville, with yoga classes and “FINtastic” dining. (Dialysis machines sold separately.)

Mr. Buffett has given his fans a path to a simulacrum of the island life. In the course of it, he’s gotten very rich. How rich? According to Forbes, in 2016 Mr. Buffett, who has only had one Top 10 song (“Margaritaville” reached No. 8), was worth a reported $550 million. (Bruce Springsteen is worth a mere $460 million, according to that same list.) He’s so rich that he’s done a 23andMe DNA test with Warren Buffett because in addition to sharing a last name, the mutual ability to sustain such mind-boggling wealth is so otherworldly that it could surely only be the result of the same extremely rare and fortunate genetic mutation. The test showed no biological relationship, but they stayed friends. Jimmy calls Warren “Uncle Warren” and Warren, who has been a business mentor to Jimmy, calls him “Cousin Jimmy.”

Uncle Warren gave Cousin Jimmy some advice while he was growing the Margaritaville empire: “Management in place,” he said. Find a good business that makes sense, and make sure there are good people running it. Jimmy Buffett didn’t just want to license his name around. He wanted to work only with people who would give the customer a great experience: “If you like what I do in goods and services, if we make you feel better after a hard day of work and you want to come blow off some steam and you pay for that, I’m going to give you your money’s worth and have a good time doing it.”

But he still has to oversee it. The problem with “management in place” is that you can employ great people, but Mr. Buffett is still the lone occupant in the Venn diagram of People Who Outearn Bruce Springsteen and People Who Are Mistaken for Men of Leisure. The work ethic his family instilled in him when he was growing up in Alabama means that he can never really hand the wheel over to someone else. “I think it was just the way I was brought up in a seafaring family,” he said. “I wanted to be in charge, like a captain of the boat.”

To be Jimmy Buffett is to understand that the Jimmy Buffett lifestyle is one not simply of leisure, but of a leisure born of resistance to middle-class convention and upward mobility: We work too many long hours, we would rather be at a bar, we would rather be Gone Fishin’, our other car is a surfboard, our other coffee mug is a beer bottle, we would rather be lying on a beach, our skin the texture of Margaritaville® Sweet & Spicy chicken wings (recipe available online!). The Jimmy Buffett lifestyle shakes its fist at the Man even while, Jimmy Buffett, with his 5,000 employees, is basically now the Man. So he is stuck with a conundrum: How do you maintain a brand that is about being chill when it is maybe the least chill thing in the world to wake up in the grip of panic about your new multimillion-dollar musical?

A FEW WEEKS before the Broadway debut of “Escape to Margaritaville,” Mr. Buffett had breakfast at the Mandarin Oriental, next to his apartment at the Time Warner Center, where he stays when he’s in town. Once, a long time ago, he left Key West because it had become too commercialized. Now he lives at the mall.

He likes being on Columbus Circle. Central Park is right there. But also, can he just say it? “I love the mall.” He eats at Bar Masa and gets coffee at Bouchon. He likes to visit the Cole Haan, hoping that one day he’ll find the right boots for a New York winter. He stops in at Bose to see what kind of new headphones they might have. But also, his whole adult life he’s been touring, and in practically every city, there’s a mall. When you don’t have a home base, the sameness of a shopping center can be a comfort.

We left the Mandarin Oriental for the theater. It was time to restart rehearsals after the holiday break. Others had been on vacation, but not Mr. Buffett. For the past week, he’d been having meetings with the bartenders and food and beverage managers at the theater. It’s not enough to sell someone a margarita. You have to make sure they feel like they’re on island time, too. “I wrote a note to the team and I said, I appreciate everything everybody’s doing but what I’m doing here, you’ve got to understand the uniqueness of where we’re doing this show in the Marquis Theater with a hotel attached with 1,800 rooms. It’s like vertical tailgating.”

He was also wondering about the end of the show. Mr. Buffett’s limo driver in New Orleans told him that the beach balls had been his favorite part. But now Mr. Buffett was wondering if they were enough. Maybe they should consider adding beads and coins, and really go hard on the Mardi Gras thing?

He’s going to speak with the ushers, too. “They’re like 60 years old, up to 80. They come out and tell you, “‘You’ve got to sit down!’ and ‘You can’t do this.’ ‘You can’t do that.’ It’s like having a schoolteacher.” Mr. Buffett wants his ushers to understand that this show is more like “Rocky Horror” than a conventional musical. “There’s an opportunity here to give people a really great, full experience,” he told them. “They’ve paid money to be here. They deserve it.”

Recently, he went to the Springsteen show on Broadway, where ushers double as military snipers, ready to do whatever is necessary to shut down phone usage or singing along. Onstage, Mr. Springsteen, whose working class anthems made him rich, revealed that he’d never been inside a factory. It’s an easy thing to admit to people who paid up to $850 for a seat. They’d assumed the factory thing was a metaphor anyway.

Mr. Buffett may no longer be Jimmy Buffett, but at one time he was. Most of the songs he’s famous for aren’t about love. They’re seemingly simple songs about how we spend our lives. But listen closer. “A Pirate Looks at Forty” is about a middle-age crisis wherein a man’s skills become obsolete before he’s ready to retire. “I have been drunk now for over two weeks” seems like a party lyric but it’s not — it’s a crushing one. “Cheeseburger in Paradise,” which he wrote after a precarious sailing trip, is about a cheeseburger, plain and simple, with a euphoric bridge that is just a list of condiments he loves. Where are our simple pleasures now, it asks without asking? Why has everything become so complicated? Why is life filled with so many things we don’t want and so few things we do?

But “It’s 5 o’Clock Somewhere” — a song he didn’t write but recorded with Alan Jackson and took out on tour — man, that one’s the real heartbreaker. Take away the jaunty island beat and you’ll find a song about a man who is so miserable that he can’t bring himself to return to work from his lunch break. “I’m getting paid by the hour, and older by the minute,” it goes. “My boss just pushed me over the limit.” The guy hasn’t taken a vacation day in a year. He knows that there will be consequences tomorrow, but he doesn’t care. He can’t face it for another afternoon. Just keep pouring those Hurricanes.

Has any pop star identified this particular strain of existential crisis better than Mr. Buffett? Who has been such a dedicated balladeer of the T.G.I.F. class? Who has been such a folk hero of workaday boredom and 9 to 5 drudgery? The knowledge that if we allow ourselves to think hard enough about our lives we will realize that they are spent in service of making someone else rich while we merely scrape by? Mr. Buffett may be rich, but he wasn’t always. He has grappled with dark thoughts about time and existence. He saw from the stage that we had, too. So he gave language to it: There has to be something more to this. There has to be a way to exist that isn’t quite so compromised. The ocean is often so far away. But a T-shirt that says “No Shoes No Shirt No Problem?” That you can take with you.

You know, he could be rewatching “Game of Thrones,” like he wants to, enjoying it even more now that he can tell the characters apart. He could be watching “Narcos,” which he loves, and vaping all day. He could be flying from house to house and kayaking and surfing. He could never work another day in his life and still dive like Scrooge McDuck into a swimming pool full of money. He could splash his name across the marquee of the Marquis and never care for a second if the musical you got was something that felt real — that really delivered escape. This is America, and poor-quality licensed products are our birthright.

But Mr. Buffett won’t give you that. He still remembers who got him here. He still shares the existential worry of how to spend a day. He protects your experience of the lifestyle he sells in a way that someone living that lifestyle should be incapable of. Look beyond the MAMA NEEDS SOME WINE sign in the Margaritaville gift shop. Look beyond the beer cozy that says “Fins to the left, fins to the right.” This is no longer a business. This is a cause. Can you hear its anthem? You can hear the Parrotheads singing it from beneath their feathers; you can hear it in their hums.

Mr. Buffett arrived at the rehearsal space. He spotted Mr. Nolan and complimented him on his tan.