Sometimes I think I was born too late.
That’s the honest truth when I think about the Jamaican music scene. I wasn’t there for the dances in the late sixties, the fever of the seventies, or the raw, urgent creation of a new cultural identity. I missed the first golden era. But even from my side of the timeline, the impact of those times—and the giants who forged them—is immediate and profound.
It’s why the news hit differently.
When I heard that Jimmy Cliff had passed away at 81, a subtle sadness settled in. In recent times, we have lost some of our musical stalwarts—like Toots Hibbert, whose sound defined a generation (read our tribute to him here: [https://kareemsquest.com/toots-a-musical-luminary/]), and then the soothings voice of Cocoa Tea (whose work you can explore here: [https://kareemsquest.com/cocoa-tea/]). Now, Jimmy Cliff. It feels like the books of that magnificent chapter are slowly closing.
But Jimmy Cliff’s book, specifically the chapter on his career, remains open, dominated by a single, powerful film role that changed everything.
Before Ivan
By the late 1960’s, James Chambers, better known as Jimmy Cliff, was already a world-renowned star. He had signed to Island Records in 1964 and moved to London to pursue a broader career under the label, which was owned and operated by Chris Blackwell (who later went on to sign Bob Marley). By 1968, Cliff gained world-wide notoriety with his smash hit, “Many Rivers to Cross,” proving his immense crossover appeal long before he ever stepped on a set.
But it was a different kind of ambition—a cinematic one—that would turn the respected singer into a global movie star.
Finding the Spirit of Ivanhoe
The film was The Harder They Come. It was an immense undertaking by writer, producer, and director Perry Henzell. Production took almost 10 years, primarily due to budgetary constraints, yet it became the film that defined Jamaica on the world stage.
I recently spoke with 84-year-old matriarch of Jakes, Treasure Beach, Sally Henzell. She was in charge of the costume for the film. Her connection to the project was personal; she was born in 1941, was her own island rebel with a deep creative streak, and her family had moved to Treasure Beach in the 1930’s, remaining there ever since.
“Those days, no one knew Treasure Beach, it was really a paradise escape,” she told me.
When she met her husband Perry, they began the challenging journey of developing his debut film. She shared the insight behind the casting choice: “Perry didn’t want an actor, he just wanted someone who captured the spirit of Ivan, and Jimmy was the person. He (Jimmy) had an album with two different versions of himself on the front and back, and that was the concept my husband was looking for.”
Jimmy Cliff’s intense dedication to the role of Ivanhoe Martin—the aspiring singer turned outlaw—was clear to everyone on set. “Jimmy took the character seriously and it showed how profound his artistic range was as an entertainer,” Sally recalled. She shared a detail that speaks volumes about the iconic look: “Jimmy came on set with his cowboy boots and they stood out so much that we kept them for his famous ‘outlaw’ shoot. As for the iconic ‘star’ shirt, both he and I drove down to Carbies to buy it.”
The film’s international acclaim was instant, largely powered by Cliff’s raw performance and the movie’s unforgettable soundtrack, which featured his own extensive work alongside other greats. The success led to Perry Henzell producing a second film, No Place Like Home, a beautiful movie, even though it was not as popular as his first. Henzell’s final project was a book, Power Game, which he hoped to adapt into a movie, but unfortunately was unable to accomplish.
From Ivan to an International Career
The acclaim for The Harder They Come made Cliff a bankable face. The authenticity he brought to the screen led to him getting more roles in the decades that followed.
Most notably, he was featured in the 1986 comedy, Club Paradise, alongside Robin Williams and Peter O’Toole. In the 1990s, he continued to contribute to major film soundtracks, a career highlight being his 1993 cover of the Johnny Nash song “I Can See Clearly Now,” which was featured prominently on the soundtrack for the hit film Cool Runnings.
His major musical milestones are too numerous to list, but they include his induction into the Rock and Roll Hall of Fame in 2010.
Childhood and the End of a Journey
Jimmy Cliff was born in St. James, near Montego Bay, a fact celebrated locally by the renaming of a street to Jimmy Cliff Blvd.
His childhood friend, Skillman, reflected on their early years to the Gleaner, painting a picture of a simple, grounded friendship before the fame: “Me and Jimmy were best friends from childhood. We grew together, go to school together, go a bird bush together, and go to mango bush together. On the weekends, we would go to show (movies) out a di crossroad,” recalled Skillman, who, at age 84, is three years Jimmy Cliff’s senior.
Skillman, who himself gave up a singing passion to run a sound system, remembered his friend’s loyalty: “He was the kind of friend that everyone would love to have. He was the best. He never ever came to Somerton and don’t check me. When mi mother dead, him come to de funeral; when my sister dead, him come a de funeral. We were always very close over the years.”
This beloved friend and global icon passed away due to complications from pneumonia. Pneumonia is an infection that inflames the air sacs in one or both lungs, which may fill with fluid or pus. While treatable, it poses a severe risk to the elderly and those with compromised health, as it was the ultimate cause of death for the 81-year-old star.
His body of work, captured forever on film and vinyl, ensures that James Chambers will always be greater than his character Ivanhoe Martin, the star in the dark-blue shirt, eternally walking away with his head held high.
