An icon in Caribbean music, a legend within the calypso art form and a powerful force in shaping calypso’s up-tempo descendant soca, Winston “Shadow” Bailey died at Mount Hope Hospital, St. Joseph, Trinidad, on Oct. 23, following complications from a stroke. He was 77.

An enigmatic musical figure, Shadow was typically attired in an entirely black ensemble covered by a cape or waistcoat and topped with a hat, all suggestive of his calypso moniker. Shadow would alternate his sung vocals with hypnotic chanted choruses, and further punctuated his onstage delivery by jumping in place. The distinctive calypso and soca rhythms he chose were characterized by heavy, unrelenting bass lines as heard on such classic compositions as “Dingolay,” a poetic ode to the power of music; “Tension,” a statement on corruption in the soca business; the deeply affecting commentary “Poverty Is Hell,” and the song that first earned Shadow attention throughout Trinidad, 1974’s “Bassman.” A recipient of countless awards throughout the Caribbean Diaspora including The Hummingbird Medal, one of the highest civilian honors bestowed in Trinidad and Tobago (T&T) for his contributions to the arts, Shadow was scheduled to receive an honorary doctorate from the University of the West Indies, Trinidad, for his lifelong contributions to the nation’s music; that recognition will be conferred posthumously on Oct. 27.

“I studied this calypso thing all alone and that’s part of my music being different,” Shadow told Billboard in an interview in Trinidad’s capital Port of Spain a few years back. “I did 'Bassman,' then I started to use melodic bass lines, not like they used before, and when I performed in the calypso tents (venues set up for the carnival season, each with their own cast of artists) in the early days, I had one extra sheet of music, just for the bass. I came up with a lot of rhythms and my thing was so sweet, I knew the others had to follow that style coming down the road.”

Born Oct. 4, 1941, in Trinidad, the larger island in the republic of Trinidad and Tobago, Shadow was raised by his grandparents on a farm in Les Coteaux, Tobago, where his earliest musical influences were the rhythms played on goat skin drums that were often accompanied by fiddle players, which he heard at local celebrations. Shadow started writing and singing calypsos at eight years old and by age 15 he was playing guitar and honing his craft “in front of the guys hanging on the corner.” At 16 he moved to Port of Spain, the birthplace of calypso, soca and the steel pan, just three of the vibrant genres the cosmopolitan city has given to the world. There Shadow auditioned for various calypso tents, enduring homelessness at various times in his early pursuit of music, as disclosed in the 2017 documentary, King From Hell, also the title of Shadow’s debut album.

The first time Shadow appeared on stage was in 1970, as part of a chorus singing in venerable calypsonian The Mighty Sparrow’s Young Brigade Calypso Tent. By 1971 Shadow was writing songs challenging the dominance of Sparrow and Lord Kitchener at the major musical competitions held throughout Trinidad’s carnival season, but his efforts went unrewarded. Shadow’s fortunes changed in 1974 with the singles “Bassman” and “I Come Out to Play.” While many said Shadow should have won that year’s Calypso Monarch title, “Bassman” was nonetheless rewarded with the Road March honors, given to the song that receives the most plays as costumed carnival revelers parade through the streets of Port of Spain; “I Come Out to Play” placed second.

“Between 1963-1973 Kitchener and Sparrow were the only Road March Winners, their sweet melodies ruled so as a youngster then, I was intrigued by the new sound of Shadow. Shadow's Threat' in 1971 asked 'dem steel band boys' to give his music a simple try, it was an announcement of things to come,” recalls Mortimer Baptiste, the Port of Spain based founding member of The Artist Vector, a non-profit organization that develops young artists and provides relief to artists in need. “Then there was the bass line that easily transitioned from Shadow's recording into one's head, just as 'Bassman' described: 'Every time ah lie down in mi bed/Ah hearing a bassman in mi head,'" Baptiste continued. “Musicians, program directors, all of us became lifelong fans of Shadow’s iconic dance, his costume and mysterious, near-mesmerizing presence. With his passing, there’s a hole in the calypso/soca firmament.”

Calypso is the first recorded music of the English-speaking Caribbean. A calypso craze swept America in the 1930s and again the 1950s; during that time Trinidadian artists sold records in significant numbers and enjoyed long term engagements at New York City nightclubs. Actor Robert Mitchum and poet Maya Angelou each recorded calypso albums and Harry Belafonte’s Calypso became the first million seller in any genre. Yet Trinidad’s calypso and its pioneering practitioners have not received their due credit for taking Caribbean music out of the region and onto the U.S. charts. Likewise, Shadow is barely known beyond the Caribbean Diaspora, despite his music having influenced a younger generation of Trinidadian superstars who now travel the world and have cracked the mainstream. Machel Montano, who has worked with Pitbull, performed on Drake’s OVO Fest and was joined onstage by Rihanna when he performed in Barbados three years ago, said Shadow was “that true African voice in calypso” from whom he derived a “tougher rhythmic structure.”

“In the 1990s era of dancehall and hip-hop, Shadow definitely struck a chord,” comments Kees Dieffenthaller, leader of popular soca outfit Kes The Band, who have sold out several New York City venues. Kes the Band also promote the annual carnival event Tuesday on the Rocks, which featured Shadow as a special guest in 2016; Kees described performing with the Bassman as a dream come true. “I got into Shadow in 1994 when he released 'Poverty Is Hell,' which grabbed the public’s attention again and influenced another generation,” recalled Kees who started out singing R&B and pop, elements he integrates into his current soca brand. “Before Shadow if you couldn’t sing and dance like Sparrow, then probably calypso and soca weren’t for you. But Shadow’s lyrical content and how he bubbled on the beat, showed me that soca doesn’t have to be run of the mill; he made it acceptable to be different. It was as if his inspiration came out of The Midnight Robber, a traditional carnival character that wears big hats, dresses in black, and comes to tell the truth. Shadow represented a different dimension in Trinidad music, he was a true original, a calypso and soca rock star.”

In Trinidad’s 2000 carnival season Shadow was crowned Calypso Monarch for his songs “What’s Wrong with Me” (which, ironically, mused on why he hadn’t been recognized with the honor after 30 years in the business) and “Scratch Meh Back,” a hilarious yet heart-rending song about aging; the acknowledgement arrived just a few weeks after Lord Kitchener passed away, which cast a pall on that year’s festivities. In 2001 Shadow secured his second Road March victory and won carnival’s Soca Monarch competition, besting contestants young enough to be his children or even grandchildren. His big hits that year -- “Stranger,” offering simple instructions to a visitor at Trinidad’s carnival, and “Yuh Looking for Horn,” a wry commentary on the relationship between financial insecurity and marital infidelity -- should have earned Shadow Calypso Monarch honors, too, according to many (he placed second).

Soca artist Bunji Garlin, whose Major Lazer produced track “Differentology” earned a 2013 Soul Train Award for Best International Performance, calls Shadow a direct influence on his development as an artist. Garlin cites Shadow’s singles “Dingolay” and “Stranger” as “two of the greatest crafted songs by any artist in any genre. The way they are lyrically constructed, no songs have had the impact that those songs had on me. What Shadow represented to me as a musician,” continued Garlin, “is being honest about your craft. Some people sacrifice substance in a song for a punch line, but Shadow came from a school where the lyrical and melodic construct were as important as everything else, he didn’t compromise. He told me stories about not being properly recognized for what he has contributed to calypso and soca, but he still had to continue contributing because when it came to his music, he wouldn’t let anything get in his way.”