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From front to back and back to front; St Bernard on the legacy of the “Mighty Shadow”

“Come here Winston. Go there Winston. Dey always pushing me around,” sang the late iconic calypsonian, Winston “Shadow” Bailey.

For that reason, I always called him Winston. I considered him my friend. He was complex and self assured about his music. I once begged him to allow me to compile a “Shadow’s Greatest Hits” album, like I did for fellow great, Leroy “Black Stalin” Calliste. His response was: “How yuh go do that? All my music great.”

I loved Winston’s charming weirdness.

Photo: The late iconic calypsonian Winston “Shadow” Bailey.
(Copyright Abigail Hadeed)

I believe Shadow is the most prolific calypso writer of all time. His music also has relevance after the Carnival season and non-West Indians can follow his story lines.

He bridged generation gaps and educated the younger music fans on the true art of calypso, soca and rapso.

In 1974, Shadow redefined Soca with “Bassman” and broke the Road March duopoly of Aldwyn “Lord Kitchener” Roberts and Slinger “Mighty Sparrow” Francisco, who scooped up every title from 1963 to 1973. Shadow’s music spoke to the youth of that era, and continues to reach and influence new generations today.

Shadow once tried to explain his secret.

“Ah moved the focus of the music from the front (horns) to the back (rhythm),” he said.

It’s a style that was picked up by a new generation of soca performers like Machel Montano and Bunji Garlin. Thank you Shadow.

Sometime ago, another famous calypsonian and now NCC chairman Winston “Gypsy” Peters noted: “Shadow has the unique ability to tell the most complex story using the least amount of words, and his lyrics can be related to by an International audience.”

Photo: Winston “Shadow” Bailey.

One only needs listen to songs like “What is Life”, “Poverty is Hell”, “Music”, “HIV” and “Columbus Lie” to see the wisdom of Gypsy’s statement. I always found Shadow’s simple line in HIV—“five minutes of sweetness could lead to a life of sadness”—to be so simple yet powerful; just like the calypsonian himself.

Stalin once argued, that Winston—as he also calls Shadow—is the real deal because “Shadow composes music for de dancehall, while still saying something… At least with Shadow a foreigner would not come to our Carnival fetes and feel all we care about is rum and woman.”

Shadow’s “Dingolay” is a thesis on music.

Like Kitchener and Sparrow, Shadow rejected the dependency syndrome that hinders many of our artistes. He opened his own tent, “The Masters Den”, and exposed talents like Daniel “Rio” Brown, Gary “Mba” Thomasos, Winston “Cro Cro” Rawlins, Doric “Funny” Williamson and Gypsy—to name a few.

He told me, when the tent was in its heyday, that “green band maxis would show up with plenty Indian people. Dey love meh yuh know. I like to bring joy to everybody.”

Shadow’s “Tempo” is a gem. It documents the events after the attempted coup and applied music which was partied to in fetes for the following carnival. Many people might have missed what his crafty declaration said the society wanted after the mayhem.

Photo: Winston “Shadow” Bailey.

In the 90’s, reggae dancehall was the choice of music for young people and DJs blasted it around the savannah in the lead up to Carnival. Shadow’s music held the interest of the reggae dancehall generation too.

I remember J’ouvert morning in 1995 when Chinese Laundry came to Woodbrook with thousands of those young reggae dancehall diehards in tow. They were blasting one song on a loop; it was Shadow’s “Gossiping.”

I argued to some of my radio DJ colleagues, Shadow and Laundry saved soca in that era.

When businessman Robert Amar invested in the Kiskadee recording label and roving tent with young artistes like General Grant, Kindred and Homefront bringing a new vibe to the music industry, it was Shadow’s influence that bridged the gap. They all learned from him and kept the focus of their music on the rhythm.

No music is sampled music by the younger generations more than Shadow’s. His influence on our recording music industry is greater than anyone.

Our three most consistent writers/performers in the recent past have been, Shadow, Stalin and David Rudder. However, for me, Shadow stands out for his ability to lyrically capture everyday issues with an international perspective.

Photo: Winston “Shadow” Bailey.
(Copyright Islandmix)

Shadow said he would not waste his time on personal political picong.

“It have people fuh dat,” he told me.

He was not interested in racially tinged music either.

“I love everybody and dey love me too,” he said.

And as to why he was not fittingly honoured in the land of birth—he received only a Hummingbird Medal (Silver) in 2003 for his contribution to music in Trinidad and Tobago.

“Dey waiting until ah dead,” said Shadow. “But de people love meh yuh know so ah does do meh ting fuh dem.”

About Eric St Bernard

Eric St Bernard
Eric A St Bernard is a host and producer of Globally WACK on WACK 90.1 FM/WACK App. He holds a MSc in TV/Radio from Brooklyn College and has worked extensively in Caribbean music formats in Trinidad and New York, as well as events promotions and media advertising.

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One comment

  1. “Dey waiting until ah dead,” said Shadow. “But de people love meh yuh know so ah does do meh ting fuh dem.”
    (Shadow’s response to the query of overdue National Awards to him)
    Was that hauntingly prophetic or what?

    The Mighty Shadow dies a few days before he would have been conferred by The University of The West Indies, ‘en vivo’, the degree of Doctor of Letters, Honoris Causa.