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

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.