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Jimmy Cliff’s 10 Best Songs: Staff Picks

Written by on November 26, 2025

Few names are as synonymous with reggae music as Jimmy Cliff.

The Grammy-winning artist, whose music traversed reggae, ska, rocksteady, soul and rock ‘n’ roll, passed on Monday (Nov. 24), as announced by his wife, Latifah Chambers, in an Instagram post.

“It’s with profound sadness that I share that my husband, Jimmy Cliff, has crossed over due to a seizure followed by pneumonia,” Chambers wrote. “I am thankful for his family, friends, fellow artists and coworkers who have shared his journey with him. To all his fans around the world, please know that your support was his strength throughout his whole career. He really appreciated each and every fan for their love.”

After amassing a handful of local hits in the mid-1960s thanks to his trademark soulful tenor, the Kingston-born star achieved his international breakthrough with his eponymous 1969 LP (released as Wonderful World, Beautiful People in the States in 1970), which included the hits “Wonderful World, Beautiful People” and “Vietnam.” Bob Dylan famously called the latter of the two singles one of the greatest protest songs he’d ever heard. Wonderful World also housed the timeless “Many Rivers to Cross,” an evergreen reflection on navigating the industry that also appeared on the soundtrack for 1972’s The Harder They Come.

The first major commercial film release from Jamaica, The Harder They Come, is a classic crime drama musical that employs several elements native to spaghetti westerns. Cliff starred as the film’s main character, tackling payola, bad faith contracts, lust, loyalty, religion, and a tireless quest for stardom. Noted for its use of Jamaican patois, The Harder They Come proved that Cliff could continue specifically dedicating his art to his people while reaching new heights internationally. By 1976, he made his Saturday Night Live performance debut ahead of a decade that included a smash hit in 1983’s “Reggae Night,” a Bruce Springsteen co-sign, and a best reggae album Grammy win for 1985’s Cliff Hanger.

Cliff’s success continued throughout the ’90s, thanks to film-adjacent hits like his 1993 cover of Johnny Nash’s “I Can See Clearly Now” (from Cool Runnings) and 1995’s Lebo M-assisted “Hakuna Matata” (from a compilation accompanying The Lion King). In the ’00s, Cliff delivered a pair of new albums (2002’s Fantastic Plastic People and 2004’s Black Magic) before Wyclef Jean officially inducted him into the Rock & Roll Hall of Fame in 2010, making the icon just the second Jamaican artist to receive the prestigious honor, after Bob Marley. In 2012, Cliff won his second career Grammy for Rebirth; ten years later, he unleashed his final studio album, Refugees.

Boasting eight top 10 projects on the Reggae Albums chart and three Billboard Hot 100 hits — “Wonderful World” (No. 25), “Clearly” (No. 18) and 1970’s “Come Into My Life” (No. 89) — Jimmy Cliff has left an indelible legacy across music and film that highlights the rich cultural heritage of Jamrock.

Here are our staff picks for Jimmy Cliff’s 10 all-time greatest songs.


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