Chris Blackwell, who built Island Records into one of most tasteful, artist-friendly and successful labels in music history, will quickly admit that, along the way, he made some grave mistakes. After seeing a formative Pink Floyd perform, he commented to a colleague “that’s the worst thing I ever saw in my life.” Upon meeting a young Elton John (then going by his birth name, Reg Dwight), he couldn’t imagine how such a shy and self-conscious kid could possibly become a viable live performer. And when Procol Harum tried to grab his attention with their unreleased song Whiter Shade of Pale, he thought its 5-min length made it unmarketable. More, he hated the use of the word “fandango” in the lyrics. “I blew that one for sure,” Blackwell said with a warm laugh to the Guardian. “But I have no regrets.” And why should he? Blackwell’s record of discovering and nurturing epochal talent vastly overwhelms any bumps along the way. He candidly details both his hits and his misses in a highly readable new memoir, The Islander: My Life in Music and Beyond. The dizzying list of stars it covers spans oceans, genres and eras, including Bob Marley, U2, Cat Stevens, Robert Palmer and Steve Winwood, who was, for years, the label’s MVP. A deeper look at his catalogue shows an uncanny knack for promoting some of Britain’s boldest acts, like King Crimson, Free, Mott the Hoople, Fairport Convention and Roxy Music, as well some of its most sensitive, like Sandy Denny, Nick Drake and John Martyn. Then there are those Island artists who cannot be classified in any way, like Grace Jones, John Cale, Marianne Faithfull and Eno. Beyond his work with the great artists of London and Jamaica, Blackwell backed fascinating creators in New York (from Eric B and Rakim to Tom Tom Club) and Africa (like King Sunny Adé and Baaba Maal). In the process, Island’s commitment to creativity often trumped its zeal for commercial success. “I’ve always been eager to work with people who are doing something new,” Blackwell said in explanation. “I’m interested in what’s different.” The roots of that interest can be traced to the island of Jamaica, where he moved with his parents from London when he was a child. For our interview, Blackwell, now 84, spoke by phone from a place he purchased long ago – Goldeneye – the storied, Ocho Rios idyll once owned by Ian Fleming that now serves as a high-end hotel. A child of notable privilege, Blackwell grew up in at atmosphere both elevated and isolated. Because he was often sick with asthma as a kid he had little contact with other children. “I spent most of my time around nurses, gardeners or the staff in the house,” he said. At the same time, his parents threw marvelous parties packed with their starry friends like Noel Coward, Ian Fleming and Errol Flynn. Blackwell’s mother was Fleming’s inspiration for the seminal Bond girl, Pussy Galore, a fact which makes the author roar with laughter. Flynn’s alcohol-soaked excesses became Blackwell’s first exposure to rock star-like indulgence, as well as an object lesson in how not to behave. He said it helps account for his ability to have remained relatively sober amid the mind-altering world of musicians. “Because I was so sick as a child I was always aware of health,” he said. “Also, when I was 11, my father went to the bar and said, ‘now you’re a grownup so you can have whatever you’d like to drink.’ The only thing I knew was whiskey. I took a sip and thought it was absolutely vile. I was never interested in alcohol afterwards.” (Ironically, he now markets his own brand of rum). Blackwell’s first exposure to the Jamaica that lay outside his cosseted life came from a near-death experience at age 21. He and some friends set sail on a small boat that ran out of fuel in a dangerously remote part of the island. Desperately in need of hydration, he set out on foot only to eventually meet a Rastafarian. “I’d never come across one before,” he said. “At the time Rastafarians were considered to be a very dangerous group of people. I was scared. But he brought me water. And I thought ‘here’s this guy who represents what everybody says are terrible people and he’s saving me.’ It changed my life.” Soon after he also opened up to a new kind of music. Blackwell’s father had helped him develop a deep love of classical music by blasting Wagner and Puccini at ear-piercing volume. Now, he found himself drawn to a very different style, emanating from the booming sound systems that amplified the ska records that had been produced by genre pioneers like Coxsone Dodd. At local live performances, Blackwell began picking out singers he liked, offering to record them with money funded by his family. Aided by his instinctual promotional skills, his first three singles shot to No 1 on the island. “It’s not because I’m a great record producer,” he said. “It’s because Jamaicans were finally hearing their own people’s music on the radio rather than music coming from England or America.” Successful as he had been on the island, he left for London after Jamaica won its independence in 1962, believing that, as an Englishman, he was on “the wrong side of history”. He arrived at an opportune time. The British blues boom was just beginning. But his first major hit was a ska recording he created for 16-year-old Jamaican Millie Small. Her distinct, high-pitched voice had intrigued him on a song he heard back on the island and, while he knew that her unusual voice could serve as a cool hook, he also understood that it could quickly grate. So, he made sure her single, the chirpy My Boy Lollipop, lasted less than 2 minutes, bucking the expected span of a song. The result “sold 7 million copies”, Blackwell said proudly. Today, he calls Small’s recording “the most important song in my life”. At the same time, it spurred him to make records that went deeper. He found an ideal voice for that after discovering the 16-year-old Steve Winwood who was, then, playing with what became the Spencer Davis Group. “I describe his voice as Ray Charles on helium,” Blackwell said. “He’s a musical genius.” The song that became the Spencer Davis Band’s first hit, Keep on Running, was written by Wilfred Edwards, a Jamaican artist Blackwell brought over to help him connect with London’s Caribbean community. The label chief soon made another pivotal discovery by bringing over an energetic young American producer, Jimmy Miller, to work with Winwood’s new band, Traffic. Miller’s recordings with them impressed the Stones enough to hire him for what became their most important albums (from Beggar’s Banquet through Exile on Main Street). Blackwell let his most interesting artists develop organically, supporting them through albums that were not big sellers. The label issued four fascinating, but quirky, albums by Mott the Hoople that bombed and a clutch of daring efforts by one of Blackwell’s pet bands, Spooky Tooth, that failed to ignite. “They were great musicians,” he said of Spooky Tooth. “But they never had the right songs.” The members of another one of his pets, Free, were incredibly young when he signed them. “The leader of the band – Andy Fraser – was 15!” Blackwell said. “I felt like they were my kids.” Yet, they were profoundly confident. When Blackwell balked at letting them use the name Free – thinking listeners would believe they could get their music for free – Fraser told him that unless the name stayed they would not sign. The band were just as adamant that Island not release All Right Now as a single, considering it a cynical throwaway. Blackwell overruled them, resulting in one of the top-selling singles of the 70s and a big money-maker to this day. One of the saddest sections of the book deals with Nick Drake, who died of an overdose of his anti-depression medicine at age 26. Though his three albums sold abysmally, Blackwell valued his work so highly that, when he sold the company in the late 90s, he put in a clause saying that Drake’s albums could never be deleted from the catalogue no matter how poorly they performed. That decision kept them in circulation long enough to inspire the use of Drake’s haunting song Pink Moon in a major ad campaign for Volkswagen that made him a star, decades after his death. Blackwell was just as instrumental in creating Bob Marley’s breakthrough. His decision to market him as a rock star made all the difference. “I felt the rhythm in the music should be a bit more rock, to reach that wide, college audience,” he said. At the same time, the other Wailers – Peter Tosh and Bunny Wailer – resented Blackwell for putting his efforts behind Marley’s solo ascent. Tosh nicknamed him “Whiteworst”, while the Jamaica’s dub pioneer Lee “Scratch” Perry, called him a bloodsucker. On the other hand, the striking, Jamaican-born artist Grace Jones found her ideal sound through his suggestions. Her first three albums, which leaned towards conventional disco, didn’t click. But for her fourth, Blackwell found her the right band (anchored by the abiding rhythm section of Sly and Robbie), gave her the right material (drawn from new wave) and issued a crucial instruction. Pointing to a picture of Jones that captured her at her most arch and imposing, he said, “this record has to sound like this picture looks.” In a similar way, a picture of Roxy Music – rather than their music – inspired Blackwell to sign them. “They just looked like stars,” he said. He had just as strong a feeling about U2, though their music didn’t speak to him personally. “I’m more bass and drums oriented and they were more high-frequency,” he said. “But I knew they would make it. All of them are really smart. And they were blessed with having a really good manager. A lot of people who manage bands are not really competent to do anything. But their manager was serious.” When U2 became massively successful, however, Blackwell was over-extended financially and, so, didn’t have the money to pay all the royalties he owed them. Instead, he offered the band a piece of Island, a move that wound up reaping them a far greater windfall than their original deal would have. Ironically, U2’s mega-success became one of the factors that helped bring about the end of Blackwell’s era of Island. Their immense popularity turned the label into a far larger company than its originator designed it to be, contributing to his decision to sell his stake. To Blackwell, another sad aspect of his career is the list of artists he worked with that didn’t live long, including Sandy Denny, Nick Drake, Jimmy Miller, Free’s Paul Kossoff and Traffic’s Chris Wood. “That’s the miserable part of the music business,” he said. At the same time, he finds great satisfaction in the artistic leaps that came from his decision to let his best talents follow their muse. “I don’t tell people what to do,” he said. ‘I encourage them to do what they can.” The Islander: My Life in Music and Beyond is out on 7 June