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The Cosmic Journey of Jimmy Cliff

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He spins by the downtown avenue that was once the throbbing, syncopated heart of the Kingston music scene. "We called this Beat Street because that's where the beat was," Cliff says. In the early 1960s, Cliff would walk to school along this corridor, which was lined with bustling record stores and labels, hoping to get discovered. "It was quite a walk, but I didn't mind it," Cliff says. "There were always lines of singers who wanted to get recordings made. Every day that I passed, I thought it was one more chance to get an opportunity."

He cruises by the building that housed Coxsone Dodd's famous Studio One, which released classic records by the Wailers and Burning Spear; across the street is sound-system pioneer Prince Buster's old store, where faded murals of Augustus Pablo and Dennis Brown are still visible on the wall. A little while later we pass by Duke Reid's Trojan Records, which still appears to be a working studio. "None of those guys ever really give me a chance," Cliff says. "I guess they just didn't like my songs."

He pulls up at the bombed-out husk of a two-story building on the corner, occupied by stray dogs and little shacks that appear to be workshops of some kind. This was Beverley's Records, where Leslie Kong – arguably the greatest reggae producer of the early period – recorded Jimmy Cliff, Bob Marley, the Maytals, Desmond Dekker, the Melodians and countless more. "I thought once of buying the place and setting it back up, like as a monument," Cliff says. "But there's nothing happening here anymore. All the buildings are broken down."

Back in 1962, when Cliff first walked into Beverley's, it was just a record store – Kong had never recorded anyone. The way it happened was Cliff was walking home from school when he noticed the store, which was run by three Chinese-Jamaican brothers, and started working out a song called "Dearest Beverley" in his head. "I told them I have some songs," remembers Cliff, who muscled his way in as they were preparing to close for the evening. "And one said to me, 'I'm not in the business.'"

"But you sell records," Cliff pointed out. "You might want to get in the business." The tallest of the brothers, the one who turned out to be Leslie Kong, told Cliff to go ahead and sing his song. "Two of the brothers laughed," said Cliff. "But this other brother told me, 'You have the best voice I've ever heard in Jamaica.' And I was like, yes! Because when you get somebody who sees in you what you see in yourself, it was a great encouragement."

Kong booked studio time and recorded Cliffs first sides, the ska classics "Hurricane Hattie," "Miss Jamaica" and "Dearest Beverley." He started getting played on the radio, booking gigs and writing songs for other artists. By 1964, his childhood dream was coming true. He was on a plane to New York, to play a Jamaican-music showcase at the 1964 World's Fair.

Cliff has something like 300 songs written over more than 50 years, and plenty of them are about love and heartbreak and good times and gold diggers (case in point: 1962's "Gold Digger," on which the teenage Cliff warns a friend about a girl who "tried to dig my gold once/I caught her hands deep down in my pants"). But the abiding theme of Cliff's music is support for the world's poorest, most vulnerable citizens – particularly in Africa, the Caribbean and South America. Unlike Marley's often overt calls to revolution, Cliff's best-known songs tend to be motivational and empowering, with lovely, uplifting melodies and arrangements to match. "I still believe that you can get it if you really want it," Cliff says, referring to his classic song, most famously recorded by Dekker. "But you need to create jobs for the people. I guess it's an international situation, isn't it? We are in a drastic time of change on the planet. Socially, spiritually, politically, ecologically, the whole cosmic situation is changing."

We're headed to the West Kingston neighborhood of Denham Town, near Marley's Trench Town, where Cliff lived in a corner of his aunt and uncle's one-room shack and was so poor he couldn't afford long pants. "It takes less fabric to make short trousers!" he points out. "But at school they made fun of me for still wearing short trousers."

Until recently, this was one of the most dangerous urban zones on the planet. In 2010, Jamaican police and military (backed by U.S. surveillance) laid siege to the housing project Tivoli Gardens – built on the former site of the Back-o-Wall Rasta encampment – in an effort to capture Christopher "Dudus" Coke, a drug lord who ruled an army of hyper-violent young gangsters. (And whose acts of charity, like paying for the neighborhood's electricity, made him an Ivanhoe Martin-style outlaw hero for many West Kingston residents.) Coke was apprehended five weeks later; at least 73 civilians were killed in the siege. He's since been extradited to the United States, and in June of this year he was sentenced to 23 years for drug trafficking. "All this was Dudus' territory," Cliff says, gazing down the road. "But this was my stomping ground."

Things have settled down: As hip-hop and dancehall booms from passing cars, Cliff pulls over at 63 3/4 Spanish Town Road, which marks the entrance to an alleyway packed with brightly painted corrugated-aluminum and plywood shanties. We climb out of the BMW and a group of teenagers appears, offering to watch the car and show us around. It's not clear at first if they know exactly who Cliff is, but they know he's someone – and people who are someone don't come around Denham Town very often.

A kid who seems to be the leader, wearing a sharp reddish-pink button-down and big diamond studs in each ear, leads Cliff through the tightly packed shacks along a mud path. He stops to greet a group of older residents – including a woman smoking a monster spliff who beams at the sight of the reggae great. We wind our way back, past younger kids returning from school in immaculate uniforms, when suddenly Cliff spots a tiny, not-entirely-weatherproof-looking blue shack. It's about as spacious as an Apollo space capsule – without running water or electricity. "This was my home," he says, peering into the dim, sparsely furnished space. "I slept right in the back there." He soaks up the energy of the place for a few minutes, and then makes his way back to the car.

When he gets there, Cliff thanks our guides, sliding a fat roll of bills out of his pocket. "Which 'o y'all the boss?" he asks, and the pink-shirt kid steps forward. Cliff breaks off several $1,000 Jamaican bills (about $11 each) and instructs him to use them to buy some drinks for the others. Then he slips another bill in each of five or so outstretched hands, gets back in the car and heads uptown.

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