Keys Weekly Exclusive With Jimmy Buffett-Streets you know by heart

On the south end of Duval Street, just before you hit the water, there used to be a restaurant flanked by red fringed umbrellas with a thatched tiki bar inside. “Logun’s Lobster House” the sign read, and if you wandered into the seaside lot on the right night in the early ’70s, you might have heard a long-haired young Jimmy Buffett play with his band.

“The first gig we did as the Coral Reefer Band, we did at Logun’s Lobster House, and it was a dollar a ticket,” says Jimmy Buffett. “David had a table on the front row, and at the table was Truman Capote, John Malcolm Brinnin, Dotson Rader, and a few other people.”

The “David” in question was David Wolkowsky, longtime friend and patron of Buffett’s. A few years before the Logun’s gig, in 1968, Wolkowsky opened the Pier House Resort at the north end of Duval Street. The Miami Herald called the opening “the turning point in Key West’s transformation from washed-up military outpost to funky tourist destination.” Wolkowsky recognized the glitter of Key West under the grime of neglect and economic depression. And he recognized something special in Jimmy Buffett. “One of the great attributes of his was his tolerance of crazy people … me included,” he says.

Buffett and Wolkowsky first crossed paths when he was taken to Key West by Jerry Jeff Walker and his girlfriend, Teresa “Murphy” Sadler. He was living in Miami and struggling to make it. “I had just come from Nashville, and I didn’t have enough money to get my own apartment.” As strange as it sounds coming from the Margaritaville mogul of today, Buffett’s past is the one that lives on in his song lyrics: flip flops and pop tops and peanut butter. The trio rolled into Key West on the momentum of Walker’s reputation, having broken into the public consciousness with “Mr. Bojangles” in ’68.

Jimmy Buffett on the water, near Key West, 1977. TOM CORCORA

“They took me to the Chart Room, and Jerry Jeff was already a force of nature in Key West in those days. That was my first time, and they kind of left me there.” After a few days of playing downtown, Buffett returned to Miami, but the island stayed with him. “I loved it so much. After I did a few gigs back in Miami, I thought … I’m going back to Key West. I had odd jobs and could play the Chart Room, and then I met David, the owner.”

Buffett’s Key West story is a familiar refrain: I met X who introduced me to Y over on Z street and 20 more years slipped away. “I ran into my now brother-in-law Tom McGuane at the Chart Room. I ended up subletting his apartment at 123 Ann Street, and then I was a Key West resident.” Buffett didn’t immediately skyrocket to fame—it would be nearly 15 years before he and Sunshine Smith opened the Margaritaville Café on Duval Street—but he fell in love with the island.

Wolkowsky was already known for championing writers, quietly supporting eccentrics and artists who have become the defining set of Key West culture. Buffett says, “He was so supportive in every way, from letting writers he knew stay there, and putting up with our nonsense.”

Buffett describes the Pier House poolside scene: a band of charming (and multi-talented) miscreants who were kept in line by Wolkowsky, playing the part of the bemused adult in the room. “I don’t think David ever paid me there, but he let me sing … and we’d just lay out by the pool and hang with the paying guests.” One of Buffett’s best friends, Larry “Groovy” Gray (it seems all of his friends had cool nicknames) ran a catamaran sailboat school on the beach at the Pier House. “Groovy always got along too, and any time David had problems with our crowd — if something had gone wrong or we stayed too late — I’ll never forget his voice, ‘Oh, Groovy,’ and that meant something had happened.” Buffett laughs. “I’m talking about real artistic support: you could lay around the pool and not get thrown out.”

He describes Key West not as a musician’s town then, but a literary town (one improvement, in his eyes, is the current Key West music scene, thanks to efforts like Charlie Bauer’s Songwriters Festival). “I was hanging with a literary crowd: Dotson Rader and McGuane and met [Jim] Harrison, and I was just a bar singer on the street.” The joke almost makes itself: Jimmy Buffett as “just a bar singer.” But he was then. “I had graduated from the university of the Chart Room and moved onto graduate work at Howie’s Lounge.” It was a time mythologized, romanticized, and riffed on by everyone from the guy at the package store to my grandmother. In ’70s Key West, literary giants, rock stars and pirates broke bread. Preferably Cuban bread.

Jimmy Buffett performing in 1976. LYNN AUERBACK

Buffett is as mythologized as Key West. Everyone has a spin on the legend, whether he’s a founding father or a prodigal son. Rumors about him trying to cash his first big check at Ed Swift’s record store, or surprise shows at Margaritaville (that one’s true), or about him being Warren Buffett’s nephew (he’s not—but he calls the billionaire “Uncle Warren” anyway) fly with the frequency of trade winds.

The Jimmy Buffett of today has grown up. He no longer resembles the long-haired, pot-smoking singer of the ’70s. The mogul-in-flip-flops has recently negotiated a licensing deal for his “Coral Reefer” brand name to be applied to medical marijuana products. According to Forbes, the Margaritaville lifestyle brand “has more than $4.8 billion in the development pipeline.” Now, it’s a white sport coat and a conglomeration. The icon of tropical escapism successfully turned what used to be a feeling into destinations around the world: bars, restaurants and even retirement homes. The Margaritaville website bills it as “a state of being” in addition to a state of mind.

But Jimmy Buffett’s voice sounds the same as it always has. That Mississippi-by-way-of-New-Orleans twang, with laughter in nearly every word. When he reminisces, his voice takes the listener on a boat ride into the past. So which of the stories are true?

The Coral Reefer Band did used to rehearse in an old gas station on Fleming Street, where Tom Corcoran also had a leather hat shop. In Buffett’s “Louie’s Backyard Days” (he lived in the house next to the restaurant on Waddell Street), “one of Tennessee Williams’s boyfriends worked at Louie’s backyard, and on one or two occasions, I was hired to play a pool party at Tennessee’s.” He demurs, “Let’s just say it was an interesting gig, and he loved Hank Williams songs.”

David Wolkowsky did invite Buffett out to Ballast Key a number of times, under the auspices of being a regular party guest, and then would say, “Oh Jimmy, bring your guitar.” And while they “hemmed and hawed” about Buffett buying Ballast Key (Buffett eventually “came to his senses”), he did sell Buffett the building that is now Margaritaville … with the stipulation that Wolkowsky got to keep the rooftop apartment at a fixed rate until his death. “I think he was 60 at the time,” Buffett laughs, “and so he had a fixed rate on the roof for as long as he lived.” Wolkowsky died this year at 99.

Sometimes the charm of today’s Key West gets overlooked in favor of nostalgia. Locals bemoan the congestion of tourists, the CVS that once was Fast Buck Freddie’s, and espouse the general “this was better when it was that” attitude. Does Buffett take credit—or responsibility—for this more commercialized version of paradise, rough edges smoothed and lawns manicured?

Jimmy Buffett and David Wolkowsky at a party in 2014. NICK DOLL/Nick Doll Photography

“I never thought it would be what it’s become, but I’m not ashamed of any part of it. I made some mistakes along the way, but today, it sure seems like an extension of what it was to us.” Buffett tells a story about filming “Tarpon,” the ’73 rogue fishing documentary for which Buffett wrote the music. “In ‘Tarpon,’” Buffett says, “they were interviewing Jim Harrison and he said, ‘Every place I’ve been to, they say I needed to be here 10 years ago.’”

“There’s a lot of people I know from those days who still live in the past,” Buffett says. “Because it was a wide-open town, still a Navy town to a degree, and it was also a primary location for the marijuana business. It was very casual, and it had that kind of pirate mentality.” Yet he attributes the enduring charm of Key West to its tolerance. “Everyone had a place there. … New Orleans was the magic city of my youth. I played on Bourbon Street, and it has that same je ne sais quoi feel that you have about a place that’s tolerant.”

His voice does that thing where you can hear it drifting out the window. “Everyone has their version of Key West. I hope that people still have that. I still smell black beans and chicken cooking when I’m riding my bike around,” he says. “It’s much more gentrified, but it still has that authenticity. … I relish the past, but I don’t live in it.”

Everyone has a version of Jimmy Buffett, too. The one we want to keep preserved in time, with his Gulf Coast drawl and his dream of escape. Does Jimmy Buffett still dream of what’s next for Key West? This version seems to have his sights set on the rest of the world, rather than the original “Margaritaville.” Since Wolkowsky’s recent passing, the old rooftop apartment above the restaurant is vacant, and Buffett muses on plans for that. “In my fantasy world,” he says, “I wanted to have a great mambo club up there. I thought it has one of the best views, and I still have the rights to the roof. … If I can get some management, I’d like to keep my mambo fantasy.”

“I don’t spend a lot of time in Key West any more,” he says, “but I might fix it up and let it be mine until I leave the planet, and have it up there, kind of in David’s honor. I think I’m going to go back to Key West and take a look at it.” Until then, we can dance in the mambo club that only exists in Jimmy Buffett’s mind.

Sarah Thomas
Sarah Thomas
Sarah Thomas is the Editor of Key West Weekly and moved down from her second-favorite island, Manhattan. She has worn many hats: publicist, tour guide, bartender, teacher, and cat wrangler, but this one seems to fit the best.

Must Read


Florida swimmers Connor Signorin and three-time Olympic gold medalist Brooke Bennett took top honors at the Swim for Alligator Lighthouse on Sept. 9. The...

Subscribe To Our Newsletter

Get Keys Weekly delivered right to your inbox along with a daily dose of Keys News.

Success! Please check your email for confirmation.