One night in August, couples dining by moonlight at an exclusive resort on Jamaica's northern coast glance up from their steamed whole fish and haute jerk chicken to take note of a latecomer who has just shuffled into the open-air restaurant. Even by relaxed island standards, the old man seems underdressed for dinner: a faded Trojan Records T-shirt, knee-length red surfer shorts, flip-flops, several days' worth of rummy-looking stubble, his mane of white hair, or what remains of it, aggressively unkempt. Leaning against the bar as if he owns the place, the man begins pecking at a smartphone, ignoring the stares, and giving the waitress, who quickly brings him a mixed drink, a nod and a wan smile.

Eventually, when his friends arrive, he sits at the best table in the restaurant, because, it turns out, he does own the place. Chris Blackwell, the 76-year-old founder of Island Records, did more than almost anyone to transform reggae from a niche, fairly provincial music into a full-fledged international pop genre. As a visionary label exec, he signed and brilliantly marketed acts like Toots and the Maytals, Jimmy Cliff, Burning Spear, Steel Pulse, Black Uhuru, Third World, Gregory Isaacs, Junior Murvin, Sly & Robbie, Lee "Scratch" Perry, and, most fatefully, a young singer-songwriter named Robert Nesta Marley. When Blackwell met the Wailers in 1971, he quickly recognized Bob Marley as a performer charismatic enough to take reggae to rock audiences with "something about his demeanor," Blackwell says simply, "that made you interested in him." And, as Timothy White notes in the Marley biography Catch a Fire, Blackwell also glimpsed a sort of kindred spirit. "Like Marley," White writes, "[Blackwell] was his own brand of eerie hybrid."

In Blackwell's case, the hybridness comes from growing up in one of the poshest En­glish families in Jamaica and yet throwing himself into the unsavory, quasi-criminal subculture that was the early record business. It comes from cultivating a reputation as the mellowest of jet-setting entrepreneurs, a decidedly anti-corporate mogul, decades before Silicon Valley tech titans made hoodies and turtlenecks acceptable in the boardroom – some years ago, when Blackwell attended an awards ceremony for Jimmy Cliff, he had to borrow a suit – and yet at the same time building Island with a stealthy single-mindedness and a ruthless set of negotiating skills. This latter cunning has earned Blackwell both props and ire. His friend Bono says, "Chris is the right tough guy to have in your corner, and he's the wrong one to have against you." Adds Jon Baker, a protégé and the founder of Gee Street Records, "Chris is a great guy, and compassionate in some ways, but he'll always say, 'Baker' – he calls me Baker – 'you have to do what's best for business.'" Jimmy Cliff, on the other hand, wrote a song about Blackwell in 1974 called "No. 1 Rip-Off Man." Sample lyric: "Helped you to build your empire, but you turned out a dirty old liar." (They've since made up.) Atlantic Records founder Ahmet Ertegun – the closest Blackwell ever had to a mentor – famously nicknamed him "the baby-faced killer."

In person, Blackwell's louche beach bum presentation is quickly undercut by an impeccably well-bred, highly ironized, very British sort of world-weariness. Time has made his eyes sad and rheumy and given his face a bejowled, hangdog quality. He speaks in a low-toned, aristocratic mumble, the voice of a man who should be narrating a book on tape by P.G. Wodehouse. He is the Dude by way of Downton Abbey, Sir Laurence Olivier wasting away in Margaritaville.

If Blackwell's contribution to popular music had stopped with bringing Bob Marley to stadiums around the world, that would have been enough, of course. But the legacy of Island Records, known in its heyday for possessing the most adventurously curated roster of any major record label, extended far beyond the sounds of Kingston to encompass Cat Stevens, Roxy Music, Tom Waits, Traffic, Marianne Faithfull, Nick Drake, Fairport Convention, Grace Jones, Brian Eno, the B-52s, King Crimson, Mott the Hoople, and U2.

"You see, Island Records never had a lot of hits," Blackwell explains. "We just had a lot of things that sold forever."

By the end of the Eighties, Blackwell sold his stake in Island for $300 million and shifted into the hotel business, first in Miami and then in Jamaica, where he currently owns several properties. Goldeneye, where he's dining tonight, once belonged to Ian Fleming, who wrote all the James Bond novels here, having purchased the 15 remote acres, including a decommissioned donkey racetrack, in 1946. While in Jamaica, Fleming snorkeled and speared fish, smoked up to 80 cigarettes a day, and carried on a long-term affair with Blackwell's mother, Blanche, who was also courted by another Jamaican neighbor, Errol Flynn. (Blackwell himself has diplomatically characterized Fleming as a "good friend" of his mother's; she turned 101 in December. "We're still not allowed to talk about the affair," one of his employees tells me.)

Blackwell bought the property in 1976 from Fleming's estate, at the behest of Blanche, and before he turned the place into a resort, he hosted friends like Sting, who wrote "Every Breath You Take" in one of the villas, and Steve Jobs, who "celebrated his 29th birthday right there," Blackwell says, nodding at a banquette area near his dinner table. Blackwell himself is famously reticent when it comes to most personal subjects. In some ways, his reserve reads as simply a British thing, though the more time you spend with the man, the more you realize there's something peculiarly Blackwellian about his inscrutability. Bono and his wife, Ali, spent their honeymoon at Goldeneye in 1982, a gift from Blackwell at a time when the fledgling band was still deeply in debt to Island. One night, the singer found himself sitting with Blanche Blackwell. Chris wasn't around, but he'd asked his mother to look after the newlyweds. Blanche didn't know the first thing about U2, but she asked Bono how he was getting along with her son on the business side of things.

Then she offered a bit of wisdom. "You know, Chris' biggest strength, and also his biggest weakness, is that he doesn't really need you as much as you need him," she said. "Remember that."

Bono asked Blanche Blackwell what she meant.

And she responded by telling this story: One night when Christopher was a child, she heard a horrible scream coming from his bedroom. Dashing to her son, she found him thrashing and wailing in his sleep, clearly in the throes of a terrifying nightmare. She shook him awake and held him in her arms, squeezing him tightly, as only a mother can do, and he sobbed and convulsed until he emerged from his dream.

At which point, fully awake, he looked up with preternatural composure and said, "OK, Mummy, you can go back to bed now."

"Age five!" Bono says, cackling at the memory. And that, in the mind of the U2 singer, has remained the story of Chris Blackwell.

One arrives at Goldeneye after passing through Oracabessa, once a hub of the local banana trade, now a sleepy town with a handful of shops, pleasingly remote compared with bustling tourist zones like Montego Bay and Negril. Behind an old metal gate, a dirt road wends through a miniature forest of banyan and mango trees, which does nothing to prepare visitors for the spectacular view of a hidden bay just past Fleming's original house. A footbridge leads down to a beachfront bar and a row of villas.

Though Blackwell has maintained residences all over the world, Jamaica remains the place where he's most at home. He loves living near the ocean and still swims and jet-skis regularly. And Jamaican culture is inexorably part of his own, no matter where he happens to be. A former Island Records employee told me about the heavy Rastafarian presence at the label's London studio in the Eighties, along with Jamaican cooks who made delicious communal meals for the entire company.

When Blackwell stays at Goldeneye, he lives in a modest two-room hut overlooking an impossibly clear lagoon. Technically, it's one room and a covered porch, all very open-air: Blackwell does not approve of air-conditioning – "Sweating is good for you," he says. "All this stuff is one of the reasons people are getting cancer. It's ridiculous" – and only grudgingly conceded to the demands of luxury tourism by installing units in the guest lodging. Framed, oversize Rolling Stone covers featuring Bob Marley and Bono hang on his walls; a small stack of books near his bed includes The Last Sultan, a biography of Ahmet Ertegun, and Brother Man, a 1954 novel by the Jamaican writer Roger Mais that's considered one of the first popular depictions of Rastafarianism. There are also, throughout the hut, framed photographs of his late wife, Mary Vinson, a fashion and interior designer Blackwell met in the early Eighties through their mutual friend Grace Jones. The couple didn't marry until 1998, finally doing so in part to celebrate the fact that Vinson's bone marrow cancer had gone into remission. The cancer eventually returned, however, and Vinson died in 2004.

While the hut is certainly understated, Blackwell, of course, also has all 52 acres of Goldeneye on which to roam freely, which he does, less like a traditional hotelier than a lord of the manor. The resort employees, who seem to appear out of nowhere bearing what food or drink he desires, no matter where on the property he ends up, feel like his personal servants. And Blackwell's fussy attention to detail, combined with his ever-present patrician air, keeps everyone on edge. While Blackwell displays an easy familiarity with the help that's certainly friendly, over the course of a few days I also watch as he tells one waiter the pepper grind is too fine, another that his rum punch doesn't taste the way rum punch is supposed to taste. A third, while clearing a table, accidentally moves a cup that Blackwell was using to prop up his iPad. The tablet falls over, and Blackwell glowers at the man and says, "You know, I had that cup there for a reason." The man nervously apologizes, and then Blackwell slowly smiles – he's just teasing!

Some mornings, Blackwell descends the stone steps leading from his hut to a private, lagoon-side bar, stocked with 15 different types of rum and only a handful of other liquors, for a breakfast of fresh fruit and scrambled eggs. Alternately, he'll dine with his guests at the rustic resort bar overlooking the beach, where the hip world music and EuroDisco soundtrack come courtesy of Radio Nova, a favorite station of Blackwell's. (If you seek out Radio Nova online, he warns, make sure it's the one based in France, not Ireland, because the latter is "terrible; they play Bon Jovi, things like that.")

After breakfast, Blackwell takes me on a tour of the grounds. Today he's wearing cargo shorts and an old T-shirt from U2's Achtung Baby tour. As we stroll along a path, two kids dash past us. They're chasing a rooster. When one of the kids, a skinny boy with glasses who looks like Harry Potter, ends up hopping onto the back of a golf cart and riding off, he calls out, "Goodbye, Father!" I wonder if I'm witnessing some sort of strange paternalistic ritual, whereby the children of Blackwell's employees refer to him deferentially as "Father," but soon I realize the boy is actually Blackwell's 12-year-old son, Chance. Later, another employee mentions that Chance and Blackwell's "baby mother" have just arrived from another part of the island. The latter, Blackwell's girlfriend, Joanna Saulter, used to work at the Marlin, one of Blackwell's Miami hotels, but she grew up in Negril in the 1970s with her hippie parents. The place was so undeveloped back then, Saulter recalls picking her dinner from the trees and walking the seven-mile stretch of the main beach without seeing another soul. Saulter's parents partnered with Blackwell in 1990 to open a luxury resort in Negril called the Caves.

It's a hot day, and as we tour a shadeless section of the property, Blackwell wraps an extra T-shirt around his head like a turban. Spotting a tree with a tumorous-looking black growth, he pauses, mid-conversation, to grab a stick and scrape at one of the ashy veins growing up the trunk. "Termites," he says, frowning. "Anyone have a match?" No one has a match. "You need to burn their nest to save the tree," he says. Later, he alerts one of the gardeners.

Along with the Caves, Blackwell owns Strawberry Hill, a resort located in an 18th-century coffee plantation in the Blue Mountains overlooking Kingston, purchased by Blackwell in 1972. A few years later, Bob Marley convalesced there after armed assailants burst into his Hope Road compound in Kingston and shot him. (Blackwell, meanwhile, "hastily chartered a private jet and left the island," writes Timothy White.) Strawberry Hill became a restaurant in the mid-Eighties and eventually a hotel. When Yoko Ono stayed there, "she thought it was going to be like the Himalayas, but you could hear sound systems blasting all night," Blackwell recalls with a chuckle, adding that she checked out after a single night. Another property, Pantrepant, a 2,500-acre cattle ranch near Montego Bay, has become an organic farm Blackwell hopes could be a model of sustainability for the island as a whole. "If you match agriculture with tourism, you're going with Jamaica's biggest assets," he says. Gesturing out at an empty field and a rocky, isolated cove, he details his plans to build 25 more huts, eventually developing the coast and expanding the tiny Ian Fleming International Airport (built largely thanks to Blackwell's lobbying efforts) and integrating an expanded tourist trade with Oracabessa. "It's really a long shot, but I want to try and create a resort town," he says. "The problem with Jamaican tourism is that it completely cuts out Jamaicans. They're natural entrepreneurs. They'll create in the worst of the worst conditions. So you need to bring the community into the loop, and encourage visitors to not be cooped up in a hotel the entire time and instead go out to a little bar or restaurant or sound-system dance or grocery store. Just like people do when they go to France or anywhere else. Without that early model of 'Come to Jamaica; you'll be perfectly safe because we look after you,' there wouldn't have been any tourism, so I don't put that down. But I think there should be a mix."

And the gate at Goldeneye?

Blackwell narrows his eyes. "There's a gate, but it's a very rural gate. You could push down that gate with a bicycle. It's the original gate Fleming had."

The sight of a pair of snorkelers approaching his cove distracts him. "Let's see what they're doing," he mutters, gazing coldly at the couple as he makes his way along a sharp, rocky inlet in bare feet. When a man and a woman emerge from the water, though, he quickly brightens, shouting, "Ah, Marco! I was about to arrest you for trespassing!" It turns out to be Marco Fila, the Italian sneaker heir, who owns 50 acres on a nearby hilltop formerly owned by Blanche Blackwell.

Making our way back to the bar, we pass a rocky stretch of beach cut off from the rest of the property by a chain-link fence. Blackwell says he owns the beach but allows area fishermen to use it; the restaurant at Goldeneye buys fish from the locals when possible, and Blackwell sponsors an annual contest in which they decorate their canoes. A group of the fishermen, all black Jamaican men, stare at us warily. "What up, CB?" one of them finally calls out. He's the youngest of the men, skinny and shirtless, with a belly button protruding at least an inch and a half from his navel. Blackwell waves, and the man peppers him with questions in patois that's incomprehensible to me. Blackwell nods, understanding everything, and responds affirmatively in standard English. In general, Blackwell speaks softly, often pausing to clear his throat with very regal-sounding ahems.

After we walk away, he says that he encourages the men not to overfish the local waters but that they don't listen. "Fishermen are very difficult to deal with: They have their own boats, they're independent, and they'll just say 'Fuck you' if they don't want to do something," he says. His tone suggests a mixture of annoyance and respect. "Very similar to musicians, actually!"

The dynamics of class and race are impossible to ignore when telling the story of both Jamaica and Chris Blackwell. The employees at resorts like Goldeneye are almost all black Jamaicans, while the guests are overwhelmingly white and privileged. Blackwell, meanwhile, would take the music of Kingston's black ghettos worldwide, but his mother's family were "members of Jamaica's old plantocracy," in the words of Ian Fleming biographer Andrew Lycett. Blackwell likes to tell the story of his first encounter with Rastafarians at age 21, when his boat ran out of gas on a remote beach; Rastas were considered dangerous at the time, and their kindness to a shipwrecked white man made a lasting impression.

Sephardic Jews who'd come to Jamaica in the 17th century, the Lindos, Blackwell's mother's family, owned sugarcane and banana plantations, bonded warehouses, and later the top-selling rum in the country, eventually becoming one of the so-called "Twenty One" elite white families of Jamaica's long colonial era. (The rough section of Kingston now known as Tivoli Gardens was once called Lindo Town.) Blackwell's father, Joseph, was a military officer of Anglo-Irish descent whose family started Crosse & Blackwell, a successful English food company specializing in jarred chutneys and relishes. Joseph Blackwell owned the best thoroughbred horse in Jamaica, Brown Bomber, as famous as Seabiscuit on the island, and also loved opera and classical music, which was all his son grew up listening to.

Young Christopher was a seriously asthmatic child, spending much of his time indoors, at times in an oxygen tent; household servants like the horse groomer and gardener became some of his closest friends.

He turned against his Catholic school after he asked a teacher if his dog could accompany him to heaven and was informed that dogs did not possess immortal souls. When the Blackwells' marriage broke up in 1945, Blanche and her son returned to England, where Chris attended Harrow, a prestigious private boarding school for boys. (Alumni include Winston Churchill and Lord Byron.) Blackwell sold liquor and cigarettes to other students out of his dormitory room. Eventually he returned to Jamaica to work at a hotel owned by his cousins, managing a water-skiing concession and getting obsessively into jazz. When a blind pianist from Bermuda named Lance Hayward gigged at the hotel, Blackwell, captivated, took him to Kingston and made a recording that became the first album Blackwell ever released. It was 1959.

Blanche Blackwell gave Chris £18,000 on his 18th birthday. With this seed money, he began traveling. In New York in 1960, he met Miles Davis through mutual friends and ended up spending three months with him, going to shows and soaking up the music of a band that also included John Coltrane and Cannonball Adderley. "Miles took a liking to me, which was strange, because he wasn't very fond of white men," Blackwell notes drily. Once, Blackwell, who had grown up listening to people like Louis Armstrong, asked Davis why he played so many bad notes. "He replied, 'I play what's in my head, rather than what I know I can play,' " Blackwell recalls. He says that's one of the greatest descriptions of jazz he's ever heard.

Meanwhile, back in Jamaica, sound systems – mobile parties thrown by disc jockeys with massive speakers, often on the backs of trucks – ruled the music scene. Blackwell, who was able to travel to the States to pick up hot rhythm and blues records, began bringing them back to the island, scratching off the labels and selling them to the sound-system DJs at inflated prices. "Now you can get anything, anywhere, instantly, but back then, it was worth it for them to have exclusives," Blackwell says. He also delivered records to the 63 jukeboxes he managed in bars throughout the country: "I would travel around with my maintenance engineer and take the records, usually five or so. A fishing town called Rocky Point, on the south coast of Jamaica – I think I was the first person of my complexion they had ever seen. And I'd put on the records and see if they liked them. It was instant American Idol. It didn't take 20 seconds. It took five seconds. 'Take it out! Take it out! We like the other one! Take it out!' "

Around this time, Blackwell dabbled in the movie business, thanks to his mother's old friend Fleming, who got him a job as a location scout on the first Bond film, Dr. No, which was being shot in Jamaica. Blackwell remembers watching the daily rushes of a bikini-clad Ursula Andress coming out of the ocean as the moment when everyone realized they had a potential blockbuster on their hands. (Before that, a veteran member of the crew had been pulling Blackwell aside and apologizing that his first film was such B-movie crap.) Sean Connery remains his favorite Bond, though he loved the recent Casino Royale. His biggest moment of Bond-related dismay came when Pierce Brosnan signed on to play 007, just because "Brosnan was so lame, and of course the first Bond film he did was GoldenEye, so I was worried it would fuck up my brand."

Blackwell was also traveling back and forth to London, where he sold ska records he'd brought up from Jamaica to immigrants in the Caribbean ghettos. Around 1963, he decided to attempt a crossover single with Millie Small, the female half of a Jamaican duo called Roy & Millie, whose single "We'll Meet" seemed to appeal to a broader audience. Millie was only 15, with a distinctive, high-pitched singing voice. Blackwell brought her to London to record with the great Jamaican guitarist Ernest Ranglin, eventually settling on a cover of a sweet – and, depending on the cast of your mind, extremely suggestive – rhythm and blues song called "My Boy Lollipop."

The single would sell 7 million copies worldwide. "Do you know how long the record is?" Blackwell asks, his face still beaming with pride. "Take a guess. Most singles go from basically four minutes and 30 seconds down. 'Lollipop' is one minute and 52 seconds!" Blackwell understood, even at such a young age, exactly how much of Millie's helium-voiced singing style audiences could take. "When the song is finished, that's great, but you haven't heard enough," he says. "If it goes on another 30 seconds, you've heard enough. And I recognized that, and cut it to that length. It's a quick fix."

Blackwell would travel the world with Millie, acting as her chaperone and, along the way, making a number of auspicious acquaintances. "Millie put me on the map," Blackwell says. "Right at the same time as the Stones hit, the Beatles hit, the Kinks, the Who, everybody in that year or 18-month period all just exploded, and 'My Boy Lollipop' was right there, and I was suddenly thrust into this world. Before Millie, I was just driving around the Jamaican parts of London selling records out of my car, and suddenly I was in the mainstream scene." In Lagos, Nigeria, where Millie was huge, Blackwell needed a last-minute backing band for his star and wound up hiring Fela Kuti. Back in Jamaica, one of Millie's opening acts was Otis Redding. When the 1964 World's Fair in Queens, New York, designated August 12 Millie Small Day, Blackwell visited Jamaica's pavilion, which was dedicated to ska music, and ended up signing a young Jamaican singer-songwriter named Jimmy Cliff, who immediately responded to the burgeoning Island aesthetic. "If you asked Chris what British groups he liked, he wouldn't say the Beatles," Cliff recalls. "He would say the Who or the Stones, because it's the more rebellious side of him." Back in England, when Millie appeared at a television studio in Birmingham, someone advised Blackwell to check out a local R&B act called the Spencer Davis Group, fronted by another youngster with a high voice, 15-year-old Steve Winwood. It became the first white act on Island.

Through Sue Records, an American label Island purchased a stake in and distributed in the U.K. as an imprint, Blackwell continued to release blues and R&B sides by Ike and Tina Turner, Elmore James, and Jimmy McGriff. But he also saw the writing on the wall, and with the rock scene exploding, he began spending more time in the U.K., producing and even touring with white rock acts like Traffic, the new psychedelic band formed by Winwood, and Free, whose "All Right Now" remains a classic-rock staple. With its distinctive pink label, and an eye-catching logo designed by the new advertising firm Saatchi & Saatchi, Island was quickly becoming the hip indie record company of its day. After hooking up with the British folk-rock producer Joe Boyd, Blackwell signed Nick Drake and Fairport Convention; Cat Stevens was lured over from Decca Records, with Blackwell advising him on how to get out of his contract (by demanding that his next album be recorded with the London Philharmonic Orchestra and Choir); Blackwell agreed to sign Roxy Music because he liked the look of their first album cover.

Adventurous prog-rock acts that have perhaps aged less well (King Crimson, Jethro Tull, Emerson, Lake & Palmer) also found a home at Island. Blackwell had the opportunity to sign Pink Floyd in 1965 after seeing them play a church hall, but passed: "They were the first band who came up with a show with visuals, but at that time, the visuals were very simple, bubbles and things like that. And you couldn't see or hear the lead singer at all." Ditto Elton John, introduced to Blackwell by Joe Cocker, whom he was managing at the time: "He came to see me, but I think he was shy or something. It seems impossible to imagine Elton John being shy! But he was so withdrawn, I felt that he's probably not somebody that could project onstage."

Jamaican music also remained an abiding love. Throughout the late Sixties and into the early Eighties, Blackwell would have a hand in releasing many of the most important records in the history of reggae: Jimmy Cliff's Wonderful World, Beautiful People, Toots and the Maytals' Funky Kingston, Max Romeo's War Ina Babylon, Junior Murvin's Police and Thieves, the Upsetters' Return of Django, Burning Spear's Marcus Garvey, Dillinger's CB 200, Steel Pulse's Handsworth Revolution, Black Uhuru's Red, Third World's 96° in the Shade, Linton Kwesi Johnson's Bass Culture.

Blackwell had long believed that the right reggae act, marketed like a black rock band to young audiences in England and the U.S., could be massive. Part of his strategy hinged on winning over the mainstream with explosive live performances. Initially, Blackwell's best hope was Cliff, whose sunny, soulful Wonderful World, Beautiful People had been Island's biggest reggae seller. Blackwell attempted to broaden Cliff's reach with The Harder They Come, a blaxploitation film with a Caribbean twist starring the singer as a musician turned criminal trying to get by in the mean streets of Kingston. Now the film is considered a classic, with a soundtrack that Rolling Stone ranked at number 122 in a list of the 500 greatest albums of all time. (It would probably make my top 30 list.) But the picture didn't do much box office at the time, and a frustrated Cliff left Island for another label's offer. A week later, Bob Marley and the Wailers paid a visit to Blackwell's office.

At last Blackwell had found the perfect vessel for his plot to infiltrate the white rock mainstream. When Marley said the group would need £4,000 to record an album – more than the Wailers had ever spent in the studio – Blackwell wrote them a check on the spot.

"Bob had been recording since 1963, so he was a kind of underground leader," Blackwell recalls. "And he had such a strong natural presence. He projected without trying to project." And yet the problem of live performance remained. Traditionally, Jamaican musicians were studio artists. Live gigs were prohibitively expensive for the average Jamaican – you needed instruments, for one thing – and sound-system DJs ruled the local clubs. "What I was suggesting to Bob didn't exist at the time, which was actually a touring, self-contained reggae group," Blackwell says.

Blackwell also found himself infuriated by the naysaying at his own record label. Bob Marley and the Wailers' Island debut, Catch a Fire, was co-produced by Blackwell, who persuaded Marley to allow Muscle Shoals guitarist Wayne Perkins to play on some tracks. After the album's release, Blackwell was dismayed when he checked in with one of his executives and discovered it had sold only 6,000 copies. That's good for a reggae record, the exec insisted. "And I remember being so disappointed and pissed off that he was just thinking of it as a reggae record," Blackwell recalls.

Of course, Blackwell's plan eventually worked, in more epic fashion than he could have ever imagined. Marley, today, remains nearly unmatched as an international musical icon. Blackwell's friend Jimmy Buffett tells a story about how, on a trip to a world music festival in Mali, the two men stopped in a tiny record shop – literally near Timbuktu! – and found a little girl selling bootleg Marley CDs. "Chris went over to her and said, 'Now, you shouldn't be doing this . . .' " Buffett recalls with obvious delight. Later, in Bamako, they caught a reunion of the legendary Malian group the Rail Band at a train station, which Buffett calls one of the greatest musical nights of his life. "With Chris, it was like royalty had come to town, like Jesus had come over the hill," he says. "They all knew he'd brought the world Bob Marley."

The rest of the Wailers would come to resent Blackwell and his focus on Marley's star power. Peter Tosh dubbed him "Chris Whiteworst" and, according to some accounts, threatened him with a machete. "He never threatened me," Blackwell insists. Bunny Wailer, on the other hand, insisted his contract be worded so that he would become a free agent if Blackwell died. When Blackwell agreed, Wailer grinned and said, "Good, now I know I can get out of the contract whenever I need to."

"Some people would say, 'He made all that money off Bob Marley,' and view it as exploitation," Blackwell says. "But there's nothing simple here. I never paid a Jamaican less than I paid the English rock acts, in terms of their royalties. To me, I couldn't do shit without my artists because I couldn't sing songs, I didn't write music. So it all basically depended on them."

Linton Kwesi Johnson, a former Black Panther and radical dub reggae poet, slammed Blackwell in a 1975 essay as a "descendant of slave masters . . . continuing the tradition of his white ancestors." But a few years later, after Johnson had a hit on Virgin Records, Blackwell was eager to sign him. When they met, Johnson recalls, "Chris was the epitome of charm." He wound up shifting to Island, and today says, "Chris Blackwell's intervention was absolutely decisive in not only putting reggae on the map but making Jamaica a brand name. He understood the music better than most people in the business, and he knew how to market it. Some of the criticisms about him may be justified, some may be unjustified, but I think he's done Jamaica a great service, and he should be respected for that."

When Marley became seriously ill with cancer, Blackwell visited him a few times in Germany, where he was receiving treatment. "At that point, you knew he wasn't recovering," Blackwell says soberly. Marley's importance to Blackwell had extended far beyond their music business partnership. "It had nothing to do with charts or sales figures," he once said. "It was something so much bigger. He was a Jamaican artist, and I am from Jamaica." While Marley's death in 1981 did not come as a shock, Blackwell was unprepared for the outpouring of love at his state funeral – particularly as the procession made its way from Kingston to the hilltop burial site. "The streets were lined all the way along," Blackwell says. "It was an incredible thing to see." In the wake of his friend's passing, Blackwell admits, "it was hard to get excited about the record business, because for me, it was such a high to have worked with him, to have seen him become so big internationally."

What did it take, I ask, for you to recover your passion about the music business? Blackwell says, "I never got back to that level again."

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."The next morning, Blackwell rises early for a long day of business meetings. Of course, for Blackwell, business meetings can be generally attended in beach attire, and they take place at his private bar overlooking the Goldeneye lagoon. Still, it's an odd scene: a 76-year-old millionaire, friend of the wealthy and powerful, spending his day attending to the most tedious minutiae of his business affairs. This particular morning he is surrounded by a half-dozen women, including Saulter, debating, in stultifying detail, what sorts of fabrics will be used for employee uniforms and bedsheets at a new hotel property.

To be fair, while Blackwell is present at all these meetings, he's not always "present," often pecking away at a smartphone or, as he does for a long stretch today, untangling a thicket of electronic-gadget cables. "Is this a battery?" he mutters, staring at a white plastic cube.

At some point, the photographer who's been shooting the hotels shows up to give Blackwell a preview of his work. He cues up a slideshow on his laptop, and as pornographically lush shots of tropical luxury flicker by on the screen, a Bob Marley song begins to play in the background. Blackwell's face lights up. "Oh, this is my favorite," he says. The photographer nods, pleased, and says that that's what someone had told him. The song is "Time Will Tell," from the 1978 album Kaya. As the beautiful images fade from one to the next, Marley's voice repeats the chorus in sharp, taunting counterpoint: Time alone, time will tell / Think you're in heaven / But you're living in hell.

If Blackwell were a different sort of fellow, we could end it right here, on this ironic juxtaposition, but CB is most certainly not living in hell. He's right where he wants to be. Or so he insists. When he began purchasing properties in Jamaica in the Seventies, he always had the long-term plan of opening hotels later in life. He says he loves paying attention to detail, that that's the secret of his success. He spends his days jetting between New York and London and Jamaica, and he still has a toe in the music business – a new Jamaican artist he's working with called Chronixx, a friend of Saulter's brother's – and his own brand of rum, a business his eldest son, 20-year-old Chris Jr., helps to run. (Blackwell also has a 46-year-old daughter, both products of different romantic dalliances.)

Another flawlessly sunny day in Oracabessa, another leisurely working lunch on the beach. There is more wine, and talk turns to the great Jamaican sprinter Usain Bolt, and later to Edward Snowden's Russian asylum. "Putin! He's such a gangster!" Blackwell cackles. Despite the difference in their ages, Blackwell and Saulter seem very much like equal partners. (If anything, Saulter is tougher than Blackwell on the help at Golden­eye.) Throughout the meal, Blackwell remains simultaneously affectionate and distant, a courtly ghost. Someone mentions a Jamaican friend who looks much older these days after recovering from a severe bout of kidney stones. "Nothing," Blackwell says softly, "ages one faster than pain."

For all his inscrutability and sangfroid, Blackwell, at heart, remains what used to be called an aesthete: a man of wealth and taste, with the emphasis on taste. In London, his limousine was an old, retrofitted cab with a fantastic sound system. In Los Angeles, he eschewed boring, fancy restaurants for business meetings, instead seeking out tiny Ethiopian joints on Fairfax, Afro-Peruvian places in East L.A. And he loved the music he released to such an extent that he's still trying to turn people onto his favorite acts. Just a few months ago, Blackwell tells me, with no small satisfaction, he had some friends listen to an old record by Ijahman – one of the most undersung Island artists, in Blackwell's opinion – and they loved it, "said, 'Where did this come from?' Even though it was made in 1978!"

More than 10 years ago, Blackwell told Rolling Stone, "I have always been kind of a loner, you know, a bit of an outsider. . . . I don't live the life of somebody who figures out who they are going to have lunch, drinks, and dinner with, going to cocktail parties and the theater. I just like building things, making things, causing things to happen and chasing ideas I'm excited about." Considered in that context, Blackwell's obsessive-seeming daily routine makes more sense. When I ask what makes him happiest these days, Blackwell says, "I love to get things done, to make things happen. I think I've been given that gift, and it's worked in different fields. And I love that. It gives me a huge amount of pleasure." As for legacy? "Well," he says, slowly, "I think I'd like to feel that I've made an impact. Ideally, a lasting impact, not just a quick flash. I would love that. That would make me feel like everything was worthwhile."