An Appreciation: Dr. Winston (Shadow) Bailey, Our Conscience

By Roger Toussaint

Roger Toussaint's remarks as delivered at a Tribute to Dr. Winston (Shadow) Bailey and Winston Scarborough, De Original De Fosto Himself - at  Brooklyn’s Tropical Paradise Ballroom, November 14, 2018, which was presented by Herman Hall, Shadow’s Agent/Manager 1978-2018.

Provided by, and published with, the expressed permission of: the Author

© 2018 -  All Rights Reserved.

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Winston Bailey
Winston "Shadow" Bailey

Greetings all! I flew in this afternoon to be here and am out tomorrow because it is truly an honor to be asked to help honor our beloved Dr. Winston Bailey, The Shadow. Many of you here today are probably more knowledgeable about his work and some of you may have even known him more intimately - a pleasure, which I did not have. Actually, my last carnival before first coming to the U.S. was 1974, the year Bassman won. As we battled that wrenching period spanning several years of adjustment to life in this country, Shadow's works were among the things that helped keep me--as it did others--anchored in our Caribbean Culture while cheating depression, if not insanity. 

Indeed, Shadow kept the Trinbagonian Village alive. He was a constant reminder of our better values and kept our Conscience in check. 

"Poverty is Hell" - performed by Shadow

Renowned for his ability to pare down emotions, feelings, experiences and language into potent and ironic catchphrases as in, “Poverty is Hell” or “We Live to Die” and the haunting “Survival”, Shadow quickly cut to the chase and laid bare our barest emotions, feelings, and experiences in language befitting a true master of the art.

He embraced and extended Valentino’s  ‘Life is a Stage far and wide offering more than 350 calypsos—really a full thesis—on every conceivable aspect of Being and of our humble place among the species in “The Story of Life. I think at the bass of his life-work was a commitment to continually challenge us to look in and Through the Mirror  and be better than our former selves and: give more than take, help more than hurt, care more for the soul as he did in  “My Belief”, pondering ‘life and its problems’.

While Shadow’s music often made us Dingolay, (sometimes even if not “Lookin’ Fuh Horn,) I’d like to touch on a few songs which I think reveal the agelessness of his work and Shadow as a man of conscience which, I dare say, has been so lacking in our governance among those who run and ruin our society.

Dr. Winston Bailey, grassroots philosopher that he is, had a knack for capturing from the simpleness to the drama and theatrics of village life in the Caribbean and presenting it as great art worthy of any Stage, Savannah, and beyond. Just witness his presentation of “Pay de Devil, (Pac Pac, Pac ... Pac, Pac) (Pac, Pac, Pac... Pay the devil... Abyssinia coming down… The children begin to tremble) and one realizes how deeply the Bassman was steeped in celebrating and preserving village life—our uncensored history. His was an intense commitment to inverting the social order by re-positioning the marginalized and “Outcasts (about which Sparrow sang so brilliantly) and their quest for equality and fair play, center stage of the national dance-floor and dialogue. And by so doing he presents calypsos not merely for revelry but, subtly, for contemplation. Our celebration of his music helped cement his imagination and the events he captured and dramatized so eloquently, into our history. Who can forget the dramatic humor of “Cook Curry & Crow”! 

Shadow’s work also exhibited a masterly treatment of complex socio-political matters.  Which calypsonian, political scientist or economist--especially those burdened with “degrees in stupidity”--can beat Shadow’s encapsulation of economic hard times, with the terse Pressure”--a thesis in which the master sings, “The cry in town is pressure”, underscoring an early allusion to an exploration of decency, “I don’t want my conscience bother me”?  Or, consider “Inflation” with “man looking for enemies and planning to fight/instead of planting peas so someone could get a bite”!

"Greed" - performed by Shadow

Again in “Greed” he calls out those opposed to true progress and a higher morality, offering:  “Greed is a kind of a sickness… You want and you want and you never satisfy.” We hear Shadow emoting not just on the street/village level but at an angle challenging us, on behalf of the poor and less fortunate, to consider man's purpose in life, “Bedtime is my greatest luxury/ I don’t want my conscience bother me.” And it is this engagement with conscience, a recurring theme in his work, which sets him apart.

"Do Good" - performed by Shadow

In “Do Good” Shadow ponders the predicament of someone who is “always in war with one’s conscience.”  There can be little doubt that Shadow wasn’t merely referencing neighbor to neighbor “schism” but more the bigger wrongs and injustices around “living in a den of luxury yet you always unhappy/ The wrong things you do like a bomb in your head.” Though we can all agree with Sparrow’s “Capitalism Gone Mad”, Shadow’s “Conscience” with its evocative “I could live nicer without conscience…/ I want to do wrong things and feel like a king” nails it. Sounds familiar? Know anyone like that – Sure! -- They ru(i)n our society, for now. 


Again, the resolute Shadow belts out in “One Love”, a desire for “equality throughout humanity.” In thinking of the long road to freedom it’s as if the great bard hears Composer’s “Workers’ Lament” in the background while rejecting the unfairness meted out to those who labor with words laced with deep understanding of class conflict: “They had my grandfather waiting for good things that come to those who wait / but he end up in a coffin poor like a church rat/ he found out too late…”

Shadow - Winston Bailey

Indeed in his quest to raise the issue of social justice and ensure a world touched by conscience, Shadow cautions us, Stoop to conquer could never be alright…/ If you want really to conqueror you gotta learn to fight! And, this soldier has been waging a musical war throughout his life against those in society hell-bent on silencing and marginalizing him by saying he was singing stupidness even though people love his music. And this is perhaps our greatest shortcoming; a failure to fully appreciate and take care of visionaries like Shadow who gave their all in taking care not only of our culture but of the very soul and conscience of our nation and region. We can and must do better!

Though Winston Bailey’s work targeted pricking the nation’s conscience, sadly even an underdeveloped sense of morality is still lacking among too many of our ‘leaders’.

"Jump Judges Jump (1976)" - performed by Shadow

I’d like to end with Shadow’s words offered in “Jump Judges Jump”, “… and when I’m gone/ my name will live on.” Get your well-deserved rest, Dr. Shadow! Plant those peas in beautiful Tobago, knowing that the Bassman will forever live in our heads, and…

…NUFF Respect to the two Winstons and let’s commit to preserving legacy as we think of ways to lighten the load of past, current, and future warrior travelers!

"Yuh Lookin Fuh Horn" - by Shadow - arranged by Clive Bradley - performed by Desperadoes Steel Orchestra

Roger Toussaint

About the Author:
Roger Toussaint, former president of the Transport Workers Union, Local 100, is a founding member of the Caribbean Awareness Committee, NY.


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