DISGRACELAND - Jimmy Buffett: Escape Artist, Incorporated.

Episode Date: September 16, 2025

Key West drug traffickers, God’s Own Bad-Ass, flying bullets, and the billion-dollar business of escape. Jimmy Buffett wasn’t just the “Margaritaville Guy” – he was a hustler, a ham, and a near pirate who turned a hangover into an empire. For a full list of contributors, visit ⁠⁠⁠⁠⁠disgracelandpod.com⁠⁠⁠⁠⁠ To listen to Disgraceland ad free and get access to weekly bonus content and more, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠⁠⁠⁠⁠. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠ Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠ (formerly Twitter)  ⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠TikTok To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoicesSee omnystudio.com/listener for privacy information.

This is exactly right. Double Elvis. When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands. I vowed. I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends.

Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea with me, Chelsea Handler, we have some fantastic guests like Amelia Clark. When like young people come up to me and they want to be an actor or whatever. My first thing is always, can you think of anything else that you can do? Rather be disappointed in. Do that.

David O'Yellowo. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts. Dennis Leary, Gaten Matarazzo from Stranger Things, Tana Monsu, Camilla Morone, Carrie Kenny Silver, and more. Listen to these episodes of Dear Chelsea on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Sometimes a suspect is found guilty before a verdict is ever read in court. On the Wicked Words podcast, I talk with the writers who dig deep into the cases that changed history,

including Marsha Clark, who went from prosecuting one of the most famous murder cases to writing crime fiction. It doesn't matter that you didn't take part in the murder. If you were at the scene at all, you're guilty of murder. Every week, the real story is revealed. Join us every Monday for new episodes of Wicked Words. Listen to Wicked Words on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Disgrace Land is a production of Double Elvis.

This is a story about escape, about drug trafficking, about God's own badass. about dodging bullets with Bono and dodging life's restrictions. This is a story about an artist I used to despise, but now kind of love. And this is a story about Jimmy Buffett. So yes, that means it's a story about great music. Unlike that music I played for you at the top of the show, that wasn't great music. That was a preset loop from my Melotron called Beaufort Can't Fish MK. 2.

I played you that loop because I can't afford the rights to torn between two lovers by Mary McGregor. And why would I play you that slice of, you know, I've never actually heard the song before, cheese, could I afford it? Because that was the number one song in America on February 14, 1977. And that was the day a son of a son of a sailor released a song called Margaritaville and changed his life forever. On this episode, drug trafficking, a badass so bad he's still walking tall. Bono dodging bullets and music history's escape artist Jimmy Buffett. I'm Jake Brennan, and this is Disgraceland.

Jimmy Buffett was not at all what you think, unless you're a head. I don't mean a parrot head necessarily, but a deep Buffett head, one who knows. his pre-parrard head history. Jimmy Buffett was an all-American badass. Jimmy Buffett swam the Key West Flats with sharks. Jimmy Buffett once fought off a bear with nothing but a lost salt shaker and his wit. Jimmy Buffett wrestled with Hemingway's ghosts and won. Jimmy Buffett drank Tom McGuane under the table,

saw more lines of Coke than Jim Harrison's one good eye. Jimmy Buffett's early Nashville records proved that he was Merrill Haggard. No, Johnny Paycheck. Jimmy Buffett knows where Bumfardo is buried. Okay, I'm exaggerating, but not by much. Also, who's Bumfardo, you ask? We'll get to that. Jimmy Buffett, the Jimmy Buffett that I thought I knew,

the one peddling not just songs, but margaritas and cheeseburgers and t-shirts and beer, and yes, even lost shakers of salt. That dude's past is not only fascinating. It directly explains how this super-dictory. charming, legendary-mastatioed, pretty okay 70s singer-songwriter was able to create a billion-dollar empire out of escapism. Because before he made it, Jimmy Buffett had to escape himself. Key West, aka Bone Island, where Florida runs out of road, where the ocean laps pink and blue scaffolding for smugglers. Nowhere left to run. If you've made it this far, to the

absolute end of American earth, they're likely not going to catch you. You've escaped. Except that Jimmy Buffett wasn't running away from anything. Instead, he was running toward something. He just didn't know it at the time. 1972, the smugglers were brazen. This was Key West in the early 70s. It was a brazen kind of town. And Jimmy Buffett watched drug traffickers unload the dope straight off the boats onto the shrimp docks, right there in the middle of the day. It was so hot it felt like the sun had a twin. Jimmy was a shrieper.

He'd grown used to the heat, but this was something else. He stood there, 24 years old, recently divorced, sweating bullets, long hair, bushy mustache, cut off jeans, nothing else, contemplating the dope on the dock. There was a lot of money in those packages. More money than he was earning from shrimping, and more than he was seeing peddling songs over at the chart room at night. Also, far more money than he'd ever made in Nashville.

The giant's fist came through the half-open passenger side window quick, landing hard on the side of Jimmy Buffett's Publiss's face. Jimmy struggled drunkenly to get the car started. The giant now had the Publiss's head cradled in his bear-like paw and was pulling, slamming the man's face. into the window. Jimmy fumbled with the ignition. He was wasted. That was the problem. He and the publicist from ABC Records, the label that signed him on account of some natural recordings, were out celebrating. They had just tied one on at Roger Miller's King of the Road motor in, and they stumbled

out, blotto, and Jimmy jumped up on top of a parked Cadillac, this giant of a man's catalac, apparently. But this wasn't any ordinary giant. Jimmy would later learn that this was Beaufort Pusser. If Jimmy Buffett was, as he claimed in one of his songs, God's Own Drunk, then Buford Pusser was God's Own Badass. As the former sheriff of McNary County in Tennessee, he'd survived two assassination attempts. He'd been shot, stabbed, too many times to count.

His wife got murdered, and old Buford here went at her killers with a determined vengeance that was and still is the stuff of legend. Buford Pusser was so badass, they made one movie, two sequels, and a TV show after him. Walking Tall. Hell, they're still making movies about him with The Rock. But at this moment, Buford Pusser was training his vengeance on Jimmy Buffett. And Jimmy Buffett, thankfully, got his car in gear and escaped. He escaped not just the violent clutches of Buford Pusser, but the soul crush of Nashville.

Jimmy arrived in Music City after a short stint in New Orleans, where he saw firsthand how to entertain people hell-bent on losing themselves in music. It was like that back home in Mississippi, too. It was like that all over, he imagined. But Nashville, Nashville was tough. As a songwriter, Jimmy didn't learn much aside from the fact that Nashville didn't think he fit in. He was forced to pick up work as a music journalist, penning notices for Billboard magazine.

And he did learn from his time at Billboard, not necessarily how to write or report. Instead, he learned that the music business is designed to steal from artists and that the music business is as craven as the smuggling business off the coast of Key West. Different commodities, different thieves, but crimes nonetheless.

In the music business, the artists are the commodity. and like shrimp off the coast of the Keys, there is always more to harvest. So if Jimmy Buffett, as an artist, was going to be treated as a commodity, then he was at least going to control the commodity. It was a valuable lesson, except the reality was harsh

because there's no value in controlling something nobody wants to buy. So Jimmy split Nashville, but not without a record contract, and landed in Key West, where he quickly learned that he was the only product in town. Here, songwriters were scarce, but writers were not. After locking down a steady-ish gig at the chart house,

where he played for tips and goodwill, and well, let's face it, the sheer fun of it, Jimmy quickly fell in with Key West's literary crowd. Guys like the celebrated author Tom McGuane, Jim Harrison, the future author of Legends of the Fall, the novelists and poet Richard Brodigan, who'd been sought out by the Beatles, time earlier, and Carl Hyacin, who would go on to write strip teas, bad monkey, and a host of other

bestsellers. Aside from writing, these guys endeavored to drink all the alcohol and do all the drugs Key West could hold. They formed an unofficial social club called Club Mandible, their mandate to inebriate and fornicate. And Jimmy Buffett fit right in. Time skipped along hazily in Key West, 1972 turned into 1973, and Jimmy Buffett sang songs at night, worked sometimes during the day, and he wrote when he was inspired, making his way back and forth to Nashville to record in her studios. His third album, 73's A White Coat and a Pink Custation, was more island than country. It wasn't novelty, but it was novel, and as such hard for the record label to find an audience for. money was tight.

Jimmy wondered what it would be like. A guy he knew told him he could make twice as much as he got paid for his last record on just one run. Buying that Boston Whaler would be no problem. And he could just escape, drift, forget it all, the grind, the unending pressure of proving to the world that you have something to say, something different, something worth hearing. And the mindfuck of knowing that that same thing that makes you different, so worthy of listening to, is the same thing that makes it so hard for people to hear you.

It was enough to want to strip it all off, leave it lying on the beach, step out onto that smuggler's boat, and never pick up a guitar again. There's two golden rules that any man should live by. Rule one, never mess with a country girl. You play stupid games, you get stupid prizes. And Rule 2, never mess with her friends either. We always say that, trust your girlfriends. I'm Anna Sinfield, and in this new season of the girlfriends, Oh my God, this is the same man.

A group of women discover they've all dated the same prolific con artist. I felt like I got hit by a truck. I thought, how could this happen to me? The cops didn't seem to care, so they take matters into their own hands. I said, oh, hell no. I vowed I will be his last target. He's going to get what he deserves. Listen to the girlfriends.

Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcast. Your husband is not who you think he is. Your body is not what you thought it was. Your identity is formed by a secret history. I'm Danny Shapiro. And these are just a few of the stunning stories I'll be exploring on the 14th season of Family Secrets.

And just then, we felt. the plane turn in the air, so much so that the bags that were under people's seats just kind of flew into the aisle. Each week, we dive head first into the complex power of secrecy, how it shapes our identities and relationships, and how it ultimately can reveal to us our truest selves. My daughter, she's pretending she doesn't know, but is trying to cook and feed me and keep me alive because I wasn't eating anything, and me pretending like everything was fine. He kind of showed me out of the way and said, move. And he went out the front door and he jumped in a car and drove off.

And that was the last time I saw him. Listen to season 14 of Family Secrets, starting May 7th on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea, with me, Chelsea Handler, we have some fantastic guests like Amelia Clark. When, like, young people come up to me and they want to be an actor or whatever, my first thing is always, can you think of anything else that you can do? Rather be. Because... Pointed in. Do that.

Dennis Leary. I wake up and I'm hitting him in the head with a water bomb. And Bruce Jenner is on the aisle in a karate stance. Like he's about to attack me. Like, making karate noises. And his entire, the Kardashians family over there, everybody's going... And the air marshal is trying to grab my arms and screaming. I immediately know that I've been sleepwalking.

David O'Yellow-O. I love this podcast. Whether it's therapy. or relationships or religion or sex or addiction or you just go straight for the guts. Guy Branham. So anyway, Nicole Kidman broke up with Keith Thurban. Being half of a country couple was always a hat she was going to wear, not like a life she was going to lead.

Oh, interesting. I like that. Did you practice that on your way over? Gaten Matarazzo from Stranger Things. Tena, monjeu, Camilla Morone, Carrie Kenny Silver. And more. Listen to these episodes of Dear Chelsea on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Jimmy Buffett was lost at sea, literally, stranded in a tiny dinghy that had been poorly nodded to a bigger boat.

The boat that the party had been on last night. Jimmy went to sleep in the dinghy and woke up floating in the middle of the Atlantic Ocean, surrounded by nothing but water and horizon in every direction. Above, the sun baked down upon him. There was nowhere to go. Which way was home? Which way spelled death? Jimmy didn't know.

Then, from far off, Jimmy heard it. The buzz of the cigarette boats engine. Traffickers. Jimmy flagged them down. And thankfully, Jimmy knew them. So incredibly, they slowed when they saw him. And despite being in the middle of a run, pointed Jimmy toward home.

Jimmy had had a hell of a run. In the four years since he arrived in Key West, he released four full-length albums, a white sport coat in a pink crustacean, living and dying in three-four time, A-1A in Havana Dreaming. He'd scored the excellent documentary, Tarpin, filmed in Key West.

It's about Key West Flats tarpins fishermen, many of them as friends. And he provided the songs for the soundtrack to a major motion picture starring Jeff Bridges, Rancho Deluxe, which was scripted by Jimmy's Key West Buddy, the novelist Tom McGuane. That's six albums in four years,

plus touring. If there was such a thing as Island Time, Jimmy Buffett's version included hustle. It was that entrepreneurial instinct Jimmy learned back in Nashville, and prior to that, from his family upbringing, being the son of a son of a sailor,

as he said. No one was coming to save his career. It was just him, and he was close. If he wanted to escape the Nashville grind, if he wanted to escape the prospect of living a life in the straight world with a nine to five, if he didn't want to spend the rest of his days singing in bars for tips, hustling one-nighters on college campuses, or worse, propped up against a beach bar yammering on about what could have been,

then something needed to change. Jimmy Buffett needed to turn his hustle into record buyers. Back in Key West, everything was changing. Bomfardo was missing, the local fire chief, the one who somehow could afford a Cadillac on a fireman's salary. A lime green Cadillac, a car that he paired with his fire engine red suits and his rose-colored sunglasses.

Florida's governor, Ruben Askew, had had enough of Key West's lack's attitude on drug trafficking. and put together a drug squad, Operation Conch. When state narcotics agents swept through town in the fall of 1975, no one was surprised when Bum Fardo got popped along with 19 other suspected drug dealers. Bum Fardo was convicted for dealing coke and pot, but before his sentencing, he disappeared, vanished. No one knew where he was. Some Key West residents told themselves,

Bum grabbed his go bag and split for South America. But most believe something else. Bum Fardo was shark bait and gone, baby gone. Jimmy Buffett laughed it off, wearing a Wairs Bum Fardo shirt on stage until he was pulled aside by a local in the know. And this fellow quietly told Jimmy that if he himself didn't like the idea of being chummed for bull sharks,

then he'd be wise to never wear that shirt again. After Bum disappeared, everything changed in Key West. With the drug dealers off the drug dealers off, the docks, the city instituted a revitalization project in 1976, and downtown was cleaned up, and a new tourism marketing plan brought in college kids, gays, and even vacationing families. There was now a strange air of overt commercialism blanketing Jimmy Buffett's adopted hometown as he set out to make his next record. Changes in latitudes, changes in attitudes, was true to its title. Like Key West in 1977, this record was about change.

It was Jimmy's first to fully feature the choral reefer band. The group that was once a fictional group of musicians Jimmy had conjured up slowly, grew into an actual touring band, then a gaggle of musicians who accompanied Jimmy along with other session players in Nashville, and finally into a band in the truest sense on changes. The album, unlike Jimmy's previous long players, Wasn't recorded in Nashville. It was made in Florida, in Miami, at Criteria, 461 Ocean Boulevard, where Eric Clapton had recently

found greatness. On changes, Jimmy collaborated with producer Norbert Putnam, whose own genius stroke was hearing Jimmy Buffett for who he was, not just a singer-songwriter, not Jim Croce or some flip-flop Chris Christopherson. He was something totally different. He was Jimmy Buffett, an artist with a completely unique point of view on the world, one that was heavily influenced by the end of the world that he'd escaped to, Key West. His lyrics reflected that island escapism,

so the album needed to sound like island escapism. It needed to sound like Jimmy Buffett, which is to say it needed to sound like a dude who just fell out of a hammock and hit his head on a tequila bottle on his way down before shaking it off, grabbing his easy widers, and rolling a spliff. Norbert Putnam went to work throwing tropical sounding instrumentation all over the recordings he, Jimmy,

and the Coral Reefer band were putting down at Criterion. Congas, steel drums, an overall laid-back feel to everything. And then, Jimmy brought in a new song, and nothing would ever be the same again. Margaritaville is a fictional place we all know. The sun never stopped shining. The whalers music plays softly in the day.

distance. Men and women, married couples, dance slowly, connected in ways they haven't been in years. The beer is ice cold, and the cocktails are just sweet enough, and nothing ever runs out. The food puts you taste buds to work. Somehow the cheeseburgers don't even make you fat. The bartender's a poet and flirts just enough to let you know you still got it going on, but not enough to piss off your spouse. And there are no hangovers, just Bloody Mary's, and a short walk to the beach where a rejuvenating dip in coral blue sea water awaits. Shoes, shirts, hell, even shorts, are all optional. What isn't optional, however, is relaxation. You feel like your best self, Margaritaville. No boss, no commute, no kids, no pressure, no problems. Except,

Margaritaville wasn't really this at all. Margaritaville was Jimmy Buffett, Solicely hung over after a gig in Texas, killing time in a Mexican strip mall restaurant before a flight, trying to drink away his headache with bottomless margaritas, while writing the lyrics to a new song of his called, well, why not? Margaritaville. That's where the song sprang from. The escapeism you hear in the storytelling of that song's lyrics, the half-of-fuck-up culpability of the protagonist. Some people say it's a woman to blame, but I know it's my own damn fault. That's Jimmy Buffett's genius. Pulling that story so simple yet so layered and so different from its actual place of origin and turning it into something else, something so powerful, that was only part of Jimmy Buffett's

superpower. The other part was what Jimmy Buffett eventually did with that song. Not only was it a hit, the signature song off of changes, Margaritaville rocketed him to a level of fame that until then had alluded him. It was the artistic spark that launched a commercial empire and the level of escapism Jimmy Buffett never

could have imagined. We'll be right back after this world, word, word. There's two golden rules that any man should live by. Rule one, never mess with a country girl. You play stupid games, you get stupid prizes.

And rule two, never mess with her friends either. We always I'm Anna Sinfield, and in this new season of the girlfriends, Oh my God, this is the same man. A group of women discover they've all dated the same prolific con artist. I felt like I got hit by a truck. I thought, how could this happen to me? The cops didn't seem to care, so they take matters into their own hands.

I said, oh, hell no. I vowed. I will be his last target. He's going to get what he deserves. Listen to the girlfriends. Trust me, babe. On the Iheart radio app, Apple Podcasts, or wherever you get your podcast.

Your husband is not who you think he is. Your body is not what you thought it was. Your identity is formed by a secret history. I'm Danny Shapiro. And these are just a few of the stunning stories I'll be exploring on the 14th season of family secrets. And just then, we felt the plain turn in the air. So much so.

that the bags that were under people's seats just kind of flew into the aisle. Each week, we dive headfirst into the complex power of secrecy, how it shapes our identities and relationships, and how it ultimately can reveal to us our truest selves. My daughter, she's pretending she doesn't know, but is trying to cook and feed me and keep me alive because I wasn't eating anything, and me pretending like everything was fine.

He kind of shoved me out of the way and said, move. And he went out the front door, and he jumped in a car and drove off, and that was the last time I saw him. Listen to season 14 of Family Secrets, starting May 7th, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This season on Dear Chelsea, with me, Chelsea Handler, we have some fantastic guests like Amelia Clark. When, like, young people come up to me and they want to be an actor or whatever,

my first thing is always, can you think of anything else that you can do? Rather be disappointed in. Do that. Dennis Leary. I wake up and I'm hitting him in the head with a water bomb. And Bruce Jenner is on the aisle in a karate stance like he's about to attack me. Like making karate noises. And his entire the Kardashian family over there, everybody's going.

And the air marshal is trying to grab my arms and screaming. And I immediately know that I've been asleep walking. David O'Yellowo. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts. Guy Branham. So anyway, Nicole Kimman broke up with Keith Thurban. Being half of a country couple was always a hat she was going to wear, not like a life she

was going to lead. Oh, interesting. I like that. Did you practice that on your way over? Gaten Matarazzo from Stranger Things. Tena Monsu. Camilla Morone, Carrie Kenny Silver. And more.

Listen to these episodes of Dear Chelsea on the IHeart Radio. app, Apple Podcasts, or wherever you get your podcasts. One hit song, Margaritaville, changed Jimmy Buffett's life. Released in 1977 on his seventh album, the song charted higher than any of Jimmy's previous singles. Margaritaville, despite its hungover origins, nailed not only what Jimmy Buffett was all about, but what Jimmy Buffett had to offer a break and escape from the grind. and it opened them up to a much larger audience.

Throughout the late 70s and early 80s, Jimmy's shows began to take on something akin to Grateful Dead concerts, but without the darkness. Jimmy's fans weren't zonked out deadheads. They were, as Jimmy's bassist at the time, the former eagle, the great Timothy B. Schmidt, coined them, parrot heads. Parrotheads are a very specific type of rock and roll fan.

First of all, they're Jimmy Buffett fans. Duh. Second, they're shameless dorks, and I mean that in the best possible way. There's no shame in wearing whatever you want in public, even if that means a Hulu skirt and a gaudy Hawaiian shirt in the middle of October. That's kind of the point. Jimmy Buffett shows are all about escaping the confines that prevent you from wearing whatever the hell you want and having fun on a work night in the middle of October. There's nothing wrong with that.

Despite the fact that every bit of fashion sense I have has led me to rebel against this tribe for as long as I can remember. But now, with age, and less punk rock piss and vinegar coursing through my veins, I kind of admire it. It's that whole so not cool it's cool type of thing, and in my mind,

nothing is cooler than not caring what other people think, which in a weird way is what your pediatrician or accountant or lawyer were doing back in the 90s and 2000s when they were going to Jimmy Buffett concerts dressed like a coconut in drag. And of course, the Parrotheads, leader himself, Jimmy Buffett,

also a shameless dork. Despite his cool 70s mustache and 3-inch in-seem cut-off jeans from back in the day, Jimmy was and always had been a shameless dork, on stage at least. He was a ham. My sense is that's who he was off-stage as well. And again, I mean that in the best way. Ask my wife who the biggest dork in the house is and she'll tell you it's me. And it's because I'm most comfortable at home,

free to act and be however I want around my loved ones who accept me for who I am. am. I believe Jimmy Buffett acted this way too, except he did it on stage every night in front of 60,000 people, which means Jimmy Buffett was totally authentic. And that tracks because it's the authentic creators and artists who developed the most devoted fans, just as Jimmy Buffett did with his parrot heads. They took their cue from Jimmy not only in fashion, and they exaggerated that whole Key West casual thing to the nth degree, but also in attitude. They bought them. They bought concert tickets and records and t-shirts and when the money started flowing for real in the mid-80s Jimmy recalled those Nashville days and the lesson he learned about control. He invested his

hard-earned capital into himself. First, before even the success of Margaritaville, Jimmy realized he was getting hosed on merch sales by bootleggers. So he opened his own beach-themed merchandise t-shirt shop in Key West in the late 70s. In 1985, he took a big swing and expanded the T-shirt shop into the Margaritaville store and cafe. Now he was serving food and drinks to fans and tourists. In 1989, Jimmy launched his own record label, Margaritaville Records, as an imprint of MCA, seizing not only creative control of his own music, but a bigger piece of the pie as well. This would last for 10 years until, in 1999, Jimmy started Mailboat Records to release his music independently. A mailboat went on to release records by artist Jimmy liked,

Boz Skaggs, Sammy Hagar, Def Leopard, Walter Becker, and more. In the year 2000, Jimmy opened a Margaritaville restaurant and casino in Las Vegas. In 2005, he launched Margaritaville Tequila. He followed that with a hotel in Pensacola, Florida, in 2011, and a resort in Orlando in 2018, and along the way he launched everything from the wildly successful Landshark Lager to beach chairs, flip-flops, frozen foods, and CBD gummies. In 1996, this billion-dollar empire in the making was doing more than keeping this son of a son of a sailor aflo. That January, Jimmy was in the air piloting his new plane, a 1954 Grumman H.U. 16 Albatross C-plane. His passenger were none other than U-2's Bono,

Bono's wife, and their two young children, aged six and three. Jimmy was hell-bent on landing in this particular area of Jamaica, because he knew of a little place with the perfect jerk chicken, jerked chicken that would blow Bono's mind. Jimmy brought the plane down with ease, and the only problem was Jimmy didn't have permission to land. As Bono and his wife and children began to make their exit, That's when it happened.

Bullets started flying. Bono, his kids, his wife, they dove back into the plane. One bullet cracked the plane's windshield. Six others peppered the rest of the plane. Jamaican authorities descended upon the plane looking for answers. Who were these drug traffickers and what made them think they could just land their plane unannounced at their small airport? There were no drug traffickers, of course.

Jimmy Buffett had sworn off that career path years ago. There was only confusion. Bono was pissed. He, his wife, his children. Once things were cleared up with authorities, they split from Miami, leaving Jimmy Buffett and his jerk chicken behind. How it all got to this point was anyone's guess.

A pissed off pop star, violent Jamaican authorities firing bullets at his plane. It wasn't Jimmy's first escape from death's clutches. He'd survived the plane crash in Nantucket a couple years prior. But where was all of this going? And what was the point? More money? For more toys?

More business endeavors? More adventure? Where's the fun and escape if it ends up killing you? Jimmy Buffett needed his own change in latitude and attitude. Throughout the 1980s and 90s, Jimmy Buffett steadily built a commercial empire that was on the verge of eclipsing his success as a musician. Not that he wasn't a success musically.

He most certainly was. He sold records. He packed stadiums with fans, but he wasn't atop the zeitgeist, and he never really was. Sure, Margaritaville was a smash, but by the early 2000s, that was decades in the rear view. And yes, Jimmy had his name and face on all manner of merchandise, but that was all fan service. Weird as it seems, even with all the success, Jimmy Buffett in 2003 was kind of a niche product. You know what wasn't a niche product in 2003? Country music. The genre was doing hundreds of millions in concert tickets in record sales

and resurging with youth in American culture beyond the Bible Belt. Country radio stations were enjoying more success than they ever had in non-traditional markets. Alan Jackson was one of country's biggest stars. So when he asked the question in his smash single, it's 5 o'clock somewhere of, what would Jimmy Buffett do? country music fans everywhere wanted to know the answer. That drink they were planning on right after work depended on it, God damn it. And Jimmy Buffett didn't disappoint.

He answered Alan Jackson in a partial duet on the hit single, singing with his trademark charm and Island Ease, and he was instantly introduced to an entire new generation of fans. The song was a smash hit. It spent eight weeks at number one on the Billboard country charts, and Jimmy's name and voice were suddenly, with an earshot of anyone in a parking lot before a sporting event, or at a beach, or in a bar on a Friday afternoon, getting out of work and in rush hour traffic with a radio

on, trying to escape the confines of their adult lives. And the song helped Jimmy escape once again. It helped him level up from being the flip-flop adventurer with a devoted but niche fan base to national treasure status, a sort of half-stone, half-loaded, poet laureate country star for partiers everywhere. The guy from that song. No, not that one, the other one. That one? No, the other one.

Jimmy was no longer the Margaritaville guy. He was Jimmy Buffett. And with this new level of success, his business is soared. So much so that he became friends with another Buffett, the billionaire investor and philanthropist Warren Buffett. I'm not sure what that means or why I think it's important to tell you that. Maybe because it underscores the fact that Jimmy Buffett was so much more than one thing.

And that's a hard legacy to leave. There's an old interview with Jimmy's friend and brother-in-law, the writer Tom McGuain. He's not talking about Jimmy, but he's being interviewed about Key West. And he quotes French poet Stefan Malarmé, in part by paraphrasing. At a point an artist dies, whatever his life was, whatever his work was, becomes one thing. that's heavy because it means that being an artist is a curse of sorts. I don't know one artist and I count myself among them who was just one thing. Jimmy Buffett's life and his work were about escaping the restrictions of being one thing.

First, it was about escaping the limitations of being a Nashville artist, then a trafficker or just another happy-go-lucky saloon singer in Key West or just a niche artist. Jimmy Buffett fought his way out of those traps with his music and he inspired millions in the process. But Jimmy Buffett was, of course, more than just one thing. He was a musician, a fisherman, a sailor, a joker, God's own drunk, a bandleader, a businessman, a father, husband, brother, and an entertainer

who gave millions of fans an off-ramp from their stressful lives, even if it was just for one night in October and not on the shores of Key West as he experienced it. He played music until the end, even staging his last performance on an island, sort of, Rhode Island. And then spending his last moments in 2003

before the cancer took him at age 76, surrounded by family, smiling and laughing, and then leaving it all on the beach and sailing away. I'm Jake Brennan, and this is Disgraceland. All right, thanks for checking out this episode of Disgraceland. Apple Podcast listeners, make sure you have auto downloads turned on. Listen, question of the week, which artist did you at one point in time despise? And now find yourself kind of digging a lot.

Jimmy Buffett is that artist for me. All right, let me know, 617-9066638, voicemail and text, to let me know which artists you didn't like before, but now I kind of can't get enough of. 617-90666-66-36-3-8 voicemail on text. You might hear your answer on the after-party bonus episode coming up right after this. Hit me up on the socials at Disgraceland Pod. Disgracelandpod at gmail.com to email me. All right, I got to go.

Here comes some credits. Disgraceland was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes page at disgracelampod.com. If you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to disgracelandpod.com slash membership.

Members can listen to every episode of Disgraceland ad free. Plus, you'll get one brand new exclusive episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelampod.com slash membership for detail. Rate and review the show and follow us on Instagram, TikTok, Twitter, and Facebook at DisgracelandPod, and on YouTube at YouTube.com slash at disgraceland pod. Rockerola. When a group of women discover they've all dated the same prolific con artist, they take matters into their own hands.

I vowed. I will be his last target. He is not going to get away with this. He's going to get what he deserves. We always say that trust your girlfriends. Listen to the girlfriends. Trust me, babe, on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. This season on Dear Chelsea, with me, Chelsea Handler,

we have some fantastic guests like Amelia Clark. When, like, young people come up to me and they want to be an actor or whatever. My first thing is always, can you think of anything else that you can do? Rather be disappointed in. Do that. David O'Yellow-O. I love this podcast, whether it's therapy or relationships or religion or sex or addiction or you just go straight for the guts. Dennis Leary, Gaten Moderato from Stranger Things, Tana Monsu, Camilla Morone, Carrie Kenny Silver, and more.

Listen to these episodes of Dear Chelsea on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Sometimes a suspect is found guilty before a verdict is ever read in court. on the Wicked Words podcast, I talk with the writers who dig deep into the cases that changed history, including Marsha Clark, who went from prosecuting one of the most famous murder cases to writing crime fiction. It doesn't matter that you didn't take part in the murder. If you were at the scene at all, you're guilty of murder. Every week, the real story is revealed. Join us every Monday for new episodes of Wicked Words. Listen to Wicked Words on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.