November 2018


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For Winston Mc Garland Bailey, a simple country boy growing up in the 40s on his grandparents’ farm in Les Coteaux, Tobago, the whole world was music – the ripple and murmur of the river, the rhythm of the waves and the “dup-dup-dup” of his running feet being hotly pursued by “crapaud music” rising from the gully. Add the reel and jig of freshly-heated Tambrin drums, ringing steel and the bright voice of a fiddle…calypso, steelpan and the Les Coteaux jab jabs’ “Pay de devil…pac pac-pac pac”. It blew his mind!

His family may have had other plans for him but from very young his mind was set: “Dey could say what dey say, and want what dey want! What about me? I supposed to say what I say and want what I want! What I want to hear is music.” He decided he would make his own music. Always beating on some ol’ bucket, he would tell them that one day he would sing calypso and that he would be “The Shadow”.

One day, he left Les Coteaux for Charlotteville where Joseph Kerr aka “Bar Joe” handed him a guitar, taught him two chords and went off to work in his garden. When Bar Joe returned, he was stunned to find that Winston had taught himself to play the instrument. He called his neighbours, “Look! I just went in my garden and leave this boy here and when I come back he playing music … and singing too”. Winston’s novice fingers were in serious pain but Bar Joe and his new audience wouldn’t let him stop. They kept a rhythm and he went on strumming late into the night. The next day they wanted more. When he returned to Les Coteaux, the question was on everyone’s lips, “How he just leave here and come back home a musician?”

Soon after, he was on his way to Trinidad to make his way as a calypsonian.

His style was unorthodox from the start. There were many detractors and numerous setbacks but Winston was (in his own words) “a stubborn little boy who grew up to be a stubborn old man”. Ever the rebel and never one to compromise his originality, he persisted, true to his unique style of composing and performing.

Today, we have the Shadow-image (the long, dark jacket or flowing cape with a broad-brimmed hat), the curious, bouncing Shadow-dance, the distinctive Shadow-sound that brought the bass line to the forefront and the very African Shadow-beat. While others found success by adapting to suit the changing musical environment, Shadow compelled us to adapt to him! He now has more than four decades of converts to his infectious “rhythmic melodies” and the philosophical poetry of his imaginative, humorous and deceptively simple lyrics.

Historian Bukka Rennie maintains that “Shadow in his very simplicity and apparent childish lyrics remains in fact our most complex calypsonian…no different [from William Blake] in his simplicity, poetic abstractions and glorifying of nature”.

Winston Bailey’s off-beat genius didn't always find favour with the judges and he eventually decided to ignore the Calypso Monarch competition. However, in 1993, after a 17-year absence, he returned to competition. Finally in 2000, the judges could deny him no longer. He took home the Calypso Monarch title with “Scratch Meh Back” and “What’s Wrong With Me?” The following year, he won both the Road March and the International Soca Monarch competition with “Stranger”, making him the only person to attain these three major titles and at 60, the oldest International Soca Monarch winner to date.

And who can forget the iconic Road March winner “Bass Man” in 1974, a year in which he also copped the Road March second place with “I Come Out to Play”, a feat that no other calypsonian or soca singer has equalled.

Mr. Bailey did not give up calypso to go plant peas in Tobago and instead has given us over 45 albums and CDs of extraordinary music that has influenced generations of calypso and rapso artists. Calypso expert Professor Gordon Rohlehr believes that “Shadow is going to be remembered for his contributions to rhythm and melody, for his strangeness, his weirdness, that sense of obeah in his music, the theme of retribution, his dedication and obsession with the music”.

His songs have been featured in major motion pictures, he has received citations from mayors in many cities, was the UN Honorary Caribbean Spokesperson on AIDS from 2001 to 2002, and in 2003 was the recipient of the Trinidad and Tobago Hummingbird Medal.

However, Mr. Bailey did not measure his success by titles and awards; for him it was truly all about the music. Winston Bailey was The Shadow, Shadow was the music, the music was Winston Bailey. As he put it: “My story never move from music … I could do plenty things without the music, but it would be empty things.”

We mourn the passing of The Shadow, The Bass Man, The King from Hell, The Dread Wizard of calypso music, and we celebrate his music.