JAMAICA | From Waldorf Triumph to National Farewell: Remembering The Hon Jimmy Cliff, OM

KINGSTON, Jamaica, December 20, 2025 - There are nights that transcend mere performance—nights when an artist doesn't simply entertain but commands history itself to bear witness. March 15, 2010, at New York's Waldorf-Astoria Hotel was such a night.

Attorney-at-Law Milton Samuda remembers it with the clarity of someone who witnessed not just a concert, but a coronation. The Honourable James "Jimmy Cliff" Chambers, OM, was being inducted into the Rock and Roll Hall of Fame, and as the snazzy ballroom pulsated with anticipation, Jamaica's reggae ambassador was about to remind the world's entertainment capital exactly who ruled their hearts.

"He was the Emperor of the night, the indisputable sovereign of entertainers as he ruled our hearts and chambers of emotions for music," Samuda recalled. The former President of the Jamaica Chamber of Commerce, invited personally by Jimmy alongside his brother Christopher, watched as the icon delivered "You Can Get It If You Really Want," "Many Rivers to Cross," and "The Harder They Come" with what he describes as "superlative aplomb and mastery."

When Wyclef Jean introduced his good friend, and Jimmy delivered his acceptance speech, something profound crystallized in that moment: this was validation not just of one man's genius, but of an entire musical movement. 

Jimmy Cliff became only the second reggae artist to enter that hallowed hall, following the posthumous induction of Bob Marley in 1994. Joining ABBA, Genesis, The Stooges, and The Hollies in that 2010 class, Jimmy proved that the sound born in Jamaica's ghettos and hills belonged among rock and roll's immortals.

The Waldorf-Astoria night was not an ending but a milestone. Jimmy would continue performing, continue representing Jamaica on global stages, continue being what Tourism Minister Edmund Bartlett would later call "a one-man global marketing campaign" for the island. But on November 24, 2025, at the age of 81, the music finally stopped. Jamaica's emperor of reggae took his final bow.

Yet even in death, Jimmy Cliff choreographed one last performance. On December 17, 2025, Jamaica gathered at the National Indoor Sports Centre not to mourn, but to celebrate exactly as Jimmy had requested. Minister of Culture Olivia "Babsy" Grange made it clear: "Jimmy didn't want a sad or sombre occasion, he wanted a celebration of his life and we are honouring his memory and his wishes."

And what a celebration it was. Beenie Man, Tessanne Chin, Nadine Sutherland, Dwight Richards, Alaine, Duane Stephenson, and Jimmy's own daughter Lilty Cliff filled the arena with music. Video tributes arrived from Ziggy Marley, Shaggy, and in a poignant full-circle moment, Wyclef Jean—the same friend who had introduced him at the Waldorf-Astoria fifteen years earlier. Prime Minister Andrew Holness and Opposition Leader Mark Golding stood united in tribute, political differences dissolved in the presence of greatness.

Jimmy's 19 children, listed lovingly by his brother Victor, his widow Latifa Chambers Cliff, and thousands of Jamaicans bore witness as the National Dance Theatre Company performed to "Many Rivers to Cross"—the same song that had mesmerized the Waldorf-Astoria and would now serve as Jamaica's final embrace of its beloved son.

The legacy Jimmy leaves behind transcends statistics, though they are impressive: Grammy winner, Rock and Roll Hall of Fame inductee, Order of Merit recipient, National Icon Award honoree. There's Jimmy Cliff Boulevard in Montego Bay, where Gloucester Avenue once stood. There are the countless visitors his music drew to Jamaica's shores, and the doors his success opened for every Caribbean artist who followed.

But perhaps the most telling measure of the man came in his final days. Even as illness claimed him, Minister Grange recalls, Jimmy was concerned about Hurricane Melissa's devastation in his native St. James, eager to return home and help rebuild. The emperor never forgot his kingdom.

From commanding the Waldorf-Astoria's glittering ballroom to receiving a nation's tearful celebration, James "Jimmy Cliff" Chambers lived a life that proved you truly can get it if you really want. And as Prime Minister Holness observed, though Jimmy has taken his final bow, "his voice will continue to echo in dancehalls, churches, and quiet moments of reflection."

The Emperor of reggae is gone. Long live the Emperor.

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