That Time Jimmy Buffett Told Hunter S. Thompson to Lighten Up, Man

Two years ago today, the world lost the legendary captain of chill, Jimmy Buffett. The world has been a profoundly sadder place ever since. And while every Parrothead from Key West to Katmandu is throwing those fins up and, hopefully, raising a salt-rimmed margarita in his honor, I’m cracking a boat drink and remembering a friendship that was as weird, wild, and wonderful as a three-day bender on Duval Street in Key West: the bond between Jimmy Buffett and the good doctor himself, Hunter S. Thompson.

When Gonzo Met Margaritaville

I’ve always been fascinated by the bromance between these two patron saints of weird. The guy who gave us “Margaritaville” and “Pirate Looks At 40” (one of the best American songs of all time) and the dude who wrote Fear and Loathing in Las Vegas were tight. I’m not entirely sure how they met (and, as a self-appointed historian of such bromances, I would love to know), but it’s likely because of Buffett’s move to Aspen, where Hunter lived nearby at Owl Farm in Woody Creek, after finally stumbling into commercial success in Nashville with his boozy ballads about tropical escapism. I imagine Buffett’s background as a former journalist for Billboard Magazine and Thompson’s employment with Jann Wenner’s Rolling Stone were good reasons to bond over strong drink and nose beers in those times.

The two were so tight, in fact, that when Hunter was in the throes of a divorce around 1980, he decamped to Key West and moved in with Buffett. This bubbles up in Alex Gibney’s 2008 Gonzo documentary about Hunter S. Thompson, where Buffett laughs about his outlaw friend. Imagine the stories those walls and boats tell.

Full disclosure: I was actually at the premiere party for that flick in New York City back in June 2008. It’s one of my few genuine life brags. I’ll never forget seeing Buffett, decked out in a white suit, wandering through the Angelika Film Center, holding court with literary titans like Gay Talese and Tom Wolfe, hooting in his signature Gulf Coast drawl about the good old days. Of course, I was just a dumb, young magazine intern at the time, so I didn’t dare get a word in with old JB.

Just wasn’t my place. A damn shame.

Anyway, there’s a million Jimbo stories I’d love to write about (like the time he played “Brown-Eyed Girl” on-stage in Florida with Phish, his court side seats at Miami Heat games, how he used to run around with Al Davis’s Oakland Raiders in the 1970s, his wonderful New Orleans and St. Barths stories, or how his book A Pirate Looks at Fifty changed my entire outlook on life), but I’m settling on this one because it feels vital. To truly get the man behind the Margaritaville empire, you have to understand the wild-eyed tribe he ran with at one point in time. His bond with the Good Doctor is ground zero for the whole damn thing.

Reddit Lore, Hammerheads and ‘That A$$hole’

And, thanks to the glorious depths of Reddit, we have some prime, unverified lore. One user shared a handful of stories from his best friend’s dad, a guy who apparently worked for Buffett in the hazy Key West days of the 70s and 80s. The dad’s first impression of Hunter S. Thompson? “That a$$hole.” Apparently, the good doctor was “always yelling at us for no reason” while the crew was busy unloading “unmarked shipping containers” for Jimmy. The dad even claims the famous lyric, “we are the people our parents warned us about,” is based on him and his cohorts. The tales only get taller from there, including a story about having to jump in the water and punch a hammerhead shark to save a drunken Buffett who had fallen overboard.

Captain Jim’s Advice To Hunter S. Thompson

The whole dynamic between the Patron Saint of Day Drinking and the High Priest of Dark Star-Spangled LSD Dreams is perfectly captured in this letter from Buffett to Thompson, dated September 13, 1996. Context is important here. When his widow, Anita, first shared the letter two years ago, she mentioned the two were kicking around the idea of a spoken-word album. Hunter was apparently getting a little too deep in the weeds about the music industry, guarded against all the sharks that swim on land.

Captain Jim, ever the voice of reason (in his own unique way), had this to say in his letter to Hunter:

“Dear Doc…

“…If anybody has been able to make a decent living out of having fun, I have. And all I can say to you as you ponder launching your recording career is, never take this sh*t seriously. Those who do, wind in the bargain bin at record stores and sulking sons of bitches who sit and blame other people for what they think would and should have been… We’re entertainers….”

….

Take Care,

“Captain Jim”

Strange Bird Aviation

Let’s just pause and appreciate the sheer perfection of that. Here’s a guy who built an empire on escapism telling the king of existential dread to, essentially, chill the hell out with trying to make a couple bucks in the recording industry. It’s the kind of advice you’d give your buddy who’s a little too good at sneaking away to the bar bathroom to do key bumps and always daydreaming about that big break, except this buddy is a multi-millionaire with a fleet of boats and a private plane.

Just chill out, man.

Acid on a Silver Tray and Jimmy’s epic Colorado Wedding

While we’re on the topic of Buffett and Thompson, let’s dive a little deeper into the lore. See, Buffett was somewhat of a rock for Hunter’s family. According to his son, Juan, in his 2016 memoir Stories I Tell Myself: Growing Up With Hunter S. Thompson, during his parents’ divorce, he spent time on Buffett’s sailboat, the Euphoria, where he was put to work as a “cabin boy.” Buffett taught Juan how to sail during a rocky summer at home.

On the other hand, there was Jimmy Buffett’s wedding to his wife Jane near Aspen, in Redstone, Colorado, near Carbondale, at a huge historic mansion high in the Rockies along the Crystal River (…great river for trout fly fishing!). According to accounts, as far as celebrity nuptials go, this was so far from a stuffy affair. They held it at the 42-room Redstone Castle, the Eagles (a fixture in the Aspen ‘70s scene) played the reception, and the invitation promised the party would rage “until it is over.” Spend a significant amount of time in the Roaring Fork Valley and you’ll hear all kinds of lore about this cast of big personalities and their many extracurriculars.

The must-follow Instagram account for every millennial-aged parrothead, Pirate Looks at 40, recently did a wonderful job digging up some old news clips about this.

You’ll also recall that Hunter’s Key West era, circa 1980, falls around the time of the filming of Where The Buffalo Roam, featuring Bill Murray as Hunter Thompson. Hence, some backstory to this picture, and the other iconic photos of Hunter piloting Jimmy’s boat.

And at the center of the storm, naturally, was Hunter S. Thompson. The night before, at the bachelor party, Thompson strutted through in a three-piece suit, reportedly offering guests acid on a silver tray and cocaine with a silver straw.

His son, Juan, later recalled being “the only child at that wedding reception,” decked out in a white tux with a walking stick, witnessing an “evening of high debauchery.” Guests stayed until 4 AM, Jimmy and Glenn jammed with the band, and $3000 worth of champagne was guzzled at the function.

Babysitting Gonzo in Paradise

I’m not sure where in the bromance timeline the wedding falls. But another major chapter between the two was Key West. Thanks to William McKeen, professor and former chairman of the Department of Journalism at Boston University, who wrote a great book on Thompson (Outlaw Journalist) and an equally great book about Key West (Mile Marker Zero: The Moveable Feast Of Key West), we have an even clearer picture of their bromance.

This is largely thanks to a guy named Tom Corcoran. Corcoran, a writer and photographer who was in the middle of it all, was allegedly tasked with “babysitting” Hunter during his stint living at Buffett’s home. And in a move that sounds like the plot of a deranged 8s comedy, the job went both ways. “Uncle Hunter” would watch Corcoran’s young son, Sebastian. His essential parenting tool was a bullhorn (allegedly). There are photos of Hunter playing front-yard football with the kid.

This whole late 1970s scene was, in a weird way, basically America’s cocaine-and-soft rock-era answer to Paris in the twenties, a sun-scorched sanctuary for a generation of artists fed up with the mainland. This scene hung out in the Rockies, in towns like Livingston, Montana and Aspen, and in Key West, which became the go-to hideout for literary heavyweights like Thomas McGuane, a legendary fishing writer who was so often called the “new Hemingway” that he was probably sick of it. McGuane ended up marrying Buffett’s sister, Laurie. If you want to read some great insight on both Hunter and McGuane, check out Terry McDonell’s 2016 memoir, The Accidental Life, about editing both of these guys during his tenure as a magazine editor at publications like Esquire and Sports Illustrated, where he was at the top of the masthead.

Anyway! This world held together by main characters like Corcoran, who McKeen documents as “sober enough to remember it all”, even as he and Hunter were collaborating on a screenplay in Jimmy Buffett’s apartment.

Grand Theft Auto and ‘Boat Drinks’

Years later, when asked by The Athletic how he managed to survive hanging with certified maniacs like Hunter (and, randomly, Al Davis-Raiders era QB Ken Stabler), Buffett gave the perfect answer of a guy who knew how to party without getting consumed by the fire. “Let’s just say I tried to keep on the perimeter of all those people,” he said. “As a child of the Mardi Gras, I had a bit of a wild side, but I always try to temper it a little bit. But when you’re around people like that, you go, ‘Man, I better watch out.’… those were some pretty wild days. I’m glad I got through it.”

Hmmm… I don’t know, Jimmy. Sorta sounds like you’re dodging the question there. But I digress. What’s in the past is certainly best left there.

Which brings me to another piece of Buffett lore that just surfaced. For years, I had a pet theory about his 1979 classic, “Boat Drinks.” Given the timeline, the song’s desperate plea to escape the frozen north—”I gotta fly to St. Somewhere / I’m close to bodily harm”—always felt like it could be about a particularly chaotic winter with Hunter in Aspen. You know, unloading pump-action shotgun rounds into some discarded appliances out at Owl Farm. Maybe it was a coded message about needing to escape after a few too many nights of shooting up freezers and dodging grapefruit.

Turns out, the reality is even better. According to his longtime collaborator Mac McAnally, the song was born out of a moment of pure, unadulterated impulse in Boston. Buffett was freezing his ass off in a Bruins sports bar when an ad for cheap Caribbean flights came on the TV. That was it. He was going. He walked outside, saw an empty cab with the keys still in it… and just stole it. Drove it straight to the airport, left it running, and bought a ticket to paradise. And he never got caught. It’s the best story I have ever heard. That spontaneous act of grand theft auto not only gave us a classic, but it also finally explains the line, “Visitors just scored on the home rink.” An absolute legend.

One Last Call to Get the Boys Back Together

Maybe Buffett was being coy because their bond was forged long before “Margaritaville” was a global brand, back when they were just two weirdos falling upwards in the Rockies. The roots run deep. Back in 1977, Buffett, the Eagles’ Glenn Fry, and Hunter S. Thompson all shared a stage at Aspen High School. After a Q&A with Hunter, Buffett—flanked by Frey—belted out one of the earliest-ever performances of “Margaritaville.” It was a perfect snapshot of their intertwined worlds: high literature and beach-bum anthems, born from the same counter-culture spirit.

Here’s the tape:

And that spirit never really died. It all strips away the cartoon versions of these guys—the caricatures that seem to live in people’s minds like Matthew McConaughey’s Moondog in Harmony Korine’s Beach Bum. The margarita-sipping beach bum and the gun-toting, drug-crazed journalist who could have been popped for a felony at any time. Forget that. What you have are two dudes who really had each other’s backs.

The depth of that bromance is hauntingly clear in one of Hunter’s final acts. On Christmas night, 2004, less than two months before he died, the writer left a message for Tom Corcoran, buzzing with excitement about getting the band back together: “I spent a lot of time talking with Buffett… and we both got very excited about the Key West years, the ‘missing years,’ the ones that you have so well documented. We’re going to reconvene down there… Let’s have ‘The Boys’ back – Chatham, McGuane, whoever’s alive. It’s going to be good.”

Hunter never got that reunion. Neither did Jimmy.

A damn shame.

But the story remains. So today, as you’re scrolling through the endless tributes to the Mayor of Margaritaville, take a moment to remember the gonzo journalist who was his partner in crime.

Pour one out for Captain Jim and the Good Doctor. Two wild-eyed American originals who doubled down on their own lanes, stuck to what made them, cared voraciously about their tribe, and lived out the very advice Buffett put in that letter: have fun, and never, ever take any of this sh*t too seriously.