The Barefoot Mogul: Chris Blackwell
Credit: Photograph by Joao Canziani

Back at Goldeneye's beachfront bar, Blackwell orders himself a rum punch and suggests I do the same. "They're very nice at this time of day," he says. It's about noon.

Eventually, a small party of other guests joins us for lunch, including an architectural photographer from New York who has been hired to shoot Blackwell's hotels, and Blackwell's girlfriend, Joanna Saulter, an acerbic, dark-haired woman about three decades his junior. Blackwell orders a Cobb salad and several bottles of rosé for the table. Three glasses in, he begins sipping from Saulter's unfinished glass. He mentions a new music project he's working on, a compilation people could play in the evening to help them fall asleep, though Blackwell adds that he personally has no problems with insomnia, noting proudly, "I could fall asleep in five minutes, right here, right now."

"Very true," Saulter mutters. "Frustratingly true."

Eventually we pile into several vehicles for a drive up to Firefly, Noël Coward's old house, now owned by Blackwell, whose mother was also a friend of Coward's. Chance and his friend run over to Blackwell's SUV, which is being chauffeured by a Jamaican with dreadlocks piled under a knit Rasta cap. "Me and my friend are coming, so no smoking weed in this car!" he tells his father.

As we motor along bumpy dirt roads, Blackwell tunes the radio to a Jamaican oldies station playing classic ska and reggae. From the back, Chance shouts a question at his father, who doesn't hear him. "CB! CB!" he cries. When he gets no response, he begins to shout, cheerily, "Deaf old man!" "He's quite something," Blackwell tells me later. "I remember how I was at 12, and I think Chance is a thousand times smarter. At my age, we didn't have television, there was no internet. We had nothing."

The Jamaica outside our window is a far cry from Goldeneye. We pass ramshackle rum bars, a long-abandoned bus stop, a little boy walking a goat on a leash. "When I was growing up, my family owned all this land," Blackwell says softly. We pass a bunch of Jamaicans playing cricket in a field. Blackwell tells the driver to stop, and we step outside so he can take some pictures. The Jamaicans glare at us, unsmiling. Blackwell doesn't pay any attention, snapping away. One of the cricket players, noting the camera, begins posing flamboyantly. At this, the crowd begins to laugh.

Henry Morgan, the real-life pirate who became rum mascot Captain Morgan after his death, operated a lookout station from the top of the mountain where Firefly is located. Blackwell's uncle sold the land to Coward. Blackwell gives me a quick tour of the surprisingly simple white home, the interior more or less mothballed since Coward's death in 1973. There's a piano, a tea set once used by the Queen Mother, an art studio where the playwright worked on amateur paintings of nude, sunbathing Jamaican men.

Outside, sipping another rum punch, Blackwell watches as the sky above the bay turns pink and gold. I ask if he's been turning Chance onto jazz yet, or maybe the sorts of classical music his own father played. Blackwell smiles and says, "No, he's been turning me onto dubstep. Skrillex." He sighs. "I try to be cool, but . . ." He trails off.

Beyond reggae, Island continued to work with some of the most interesting artists of the Seventies and early Eighties, including Richard and Linda Thompson, Brian Eno, Marianne Faithfull, and John Cale. Blackwell admits that, aside from the Slits, Island completely missed the boat on punk, a genre he never loved. But he personally produced several wild avant-disco records by Grace Jones, an Amazonian model he signed after seeing her photograph in a magazine. (At one recording session, he blew up a photograph of Jones to five feet by five feet and had it pinned up in the studio, telling the musicians, "This record's got to sound like that looks.") And when Elektra Records refused to release Tom Waits' Swordfishtrombones, an experimental move away from the boozy late-night crooning of his earlier recordings, Blackwell quickly offered him a deal. (Waits told Billboard that in subsequent years, Blackwell never ceased to remind him that one of the songs ended on a "sour note . . . as if he'd bought a new car with a scratch on the hood and he didn't want me to forget it.")

And of course, there was that night in 1979 when Blackwell was persuaded to slip away from a Marley concert at London's Crystal Palace to check out a scrappy rock band from Dublin playing a tiny punk club. "Chris' flip-flops made the biggest impression," recalls Bono. "It was the middle of winter. There was something very flagrant about him, and the way he related to the aesthetic du jour, that made him so much more punk than a lot of people in the room." Blackwell didn't initially love U2's music. "I love black music, and jazz, and this was very trebly," he once said. But he was immediately drawn to the band, and insisted on sticking by them, even after their second album, October, flopped.

After Marley's death, though, Blackwell struggled to find his place in a music business he'd helped to create. With the advent of MTV, he became convinced that video would be the future of the industry and shifted his focus to Island's film division. By the late Eighties, he felt Island had become too large, no longer a family affair. "I started to wonder, 'What is so special about us?' " Blackwell says. "I felt that we had lost our USP. That's an advertising expression: unique selling position. In other words, I felt that we'd had something unique and we had lost it."

After selling Island to Polygram, Blackwell stayed on as president of the label for a few years, though eventually he had a falling out with the new owners over his continued desire to focus on visual elements of music, with an audio-visual label he wanted to start called Island Visual Arts. In a fit of pique, Blackwell left Island and started Palm Pictures, a film and music production company that was meant to further this fusion of the two mediums; it would become the biggest business failing of Blackwell's career. "It was stupid, because I was driven by my being upset about not getting my own way," Blackwell admits today. "And of course, jumping from something that had been running for 30 years, with a big catalog – it was very difficult. And then my wife got sick, so . . . It didn't work too well."

Blackwell, ever reticent, unsurprisingly shuts down conversations that lead back in the direction of his late wife. At one point, he fondly recalls trekking through Africa with her, seeking out interesting fabrics for her Manhattan home-furnishing store, Royal Hut. (Mary Vinson kept her own hut adjacent to Blackwell's at Goldeneye, and the resort's batik towels and robes come from the Royal Hut collection. "I design, basically, what I need for our life together," she told The New York Times in 2001.) "I'll tell you the truth, I know nothing about fashion," Blackwell says, and when I ask if Vinson made any attempts to get him out of the shorts and flip-flops, he says, "She did. But it was a losing battle."

"The various fiefdoms of film, or music, or hotels, or whatever it is, they will rise and fall and rise again," says Bono. "But that's not who Chris is, and that's not really adversity to Chris. Adversity to Chris was losing Mary. Adversity to Chris was losing Bob Marley, and other friends along the way. But Mary's got to be at the top of the list, because it took him a long time to get to a place where he could surrender fully to a woman, and when he did . . ." There's an eight-second pause as the singer chooses his words. "She disappeared. They had some years, but not enough. And that, I think, is the biggest tragedy of his life."