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

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.