Shadowing The Shadow


Above: Shadow at Dimanche Gras, 2003. Photo by Mark Lyndersay.

A life as stalking penumbra

Story and photos by Mark Lyndersay. Originally published in the Newsday Carnival Souvenir 2018.

The Mighty Shadow (Winston Bailey) struck a chord in my soul when I was a teen and like a crazed tuning fork, it’s resonated throughout my life.
I think we all felt it in 1974, the urgent release of his music, songs that rippled with a frisson of desperation and frustration.
From the first lines of Bassman, I identified.

“I was planning to forget calypso
and go and plant peas in Tobago
But I am afraid,
I can’t make the grade…”

Here was a man caught between fear and passion, trapped between a career he felt was going nowhere and the greater terror of abandoning it, and who among us hasn’t heard the insistent call of our own bassman, demanding that we return to a calling that shows us neither love nor reward.

In 1974 I had my own choices to make. To study work that no longer interested me – with the exception of English Literature and specifically Shakespeare – I cared little for my A-Level courses. Or I could write, albeit badly but with undimmed enthusiasm.

Winston Bailey in that year was my standard bearer for the hard, apparently impossible choices and the enthusiasm with which the prancers on the road took up his songs suggested it was possible to embrace one’s muse with a measure of success.

A portrait of The Shadow taken during the photo session for the Kiskidee album Moods of the Shadow. Photo by Mark Lyndersay.

So for four and a half decades I was his penumbra, a quiet stalker on the fringes. I reported on his performances and apparently inescapable conflicts with calypso’s musical authorities.
I interviewed him as a bemused calypsonian at the Master’s Den, the tent he led briefly, starting in 1979.
I photographed him from stage side, capturing within the camera’s rectangle a man who conspicuously defied boundaries of any kind.

In 1993, I photographed him for the cover of his second album with Kisskidee Records. I offered him some Witchhazel, my standard fall back for controlling shine on men when there’s no makeup artist available.
He looked cooly at the uncapped container.
“I don’t know what you have in your bottle,” he said quietly.

I sent to the pharmacy for a fresh bottle and the shoot proceeded.
Shadow could have had a very different career, one suspects. As a musician, he understood what made people dance and as a lyricist, he knows what kept people interested, but he pressed those skills into a discography that bears a rare stamp of uniqueness and singular perspective in the calypso pantheon.
Shadow’s songs are Winston Bailey’s life, clearly and indelibly.

Nobody ever had to ask The Mighty Shadow his opinion on anything. He recorded it all in a vast catalogue of 28 albums and 37 singles and EPs.
Infuriated with the widespread theft of his music, he took the fledgling industry of IP thieves to task in 1983’s Pirates.
When he grew tired of the arbitrariness of the judging in national calypso competitions, he spat in their eye with 1977’s Jump Judges Jump and broke the Savannah with it at that year’s clash of the tents.

“The world know my music.
It solid like brick,
The people enjoy it,
They dance to the beat,
But when they have competition,
The judges will swear
I am a comedian,
so I ent going back there.”

Shadow at Dimanche Gras 2001. Photo by Mark Lyndersay.

Shadow would not keep that promise. He would compete in the Soca Monarch competition and the Calypso Monarch competition winning another road march in 2001 with Stranger, one of his more direct dance numbers.

If there can be said to be throwaway Shadow songs, it is these party-focused songs of which there are relatively few, including the remorselessly cheerful Roll that Bumbulum, a rocksteady Charlane and the triple time Shift yuh Carcass, the spiritual predecessor of Rose’s Leave me alone.
In balance, you will find in his catalogue of music, a song of counterpoint that speaks directly to his existentialist musings.

Story of Life is a nihilistic view of the cycle of life, while My Belief, one of my personal favorites, is a celebration of the fulfilling minutiae of daily existence.

“I believe in the stars in the dark night
I believe in the sun and the daylight,
I believe in the little children
I believe in life and its problems
Rob me, beat me, cheat me, but you can’t change me.”

Shadow performing at the 2007 Dimanche Gras held at the Jean Pierre Complex. He placed tenth. Photo by Mark Lyndersay

Shadow is philosophical, both dazzlingly mundane and extravagantly worldly, funny when he chooses to be and utterly preoccupied with infidelity and the consequences of horn.
But for all the many amazing songs that Shadow has created in his house of music, there is probably no purer distillation of his ability to lift a spirit with quirky observations, heartfelt love and a danceable beat than 1994’s Dingolay.

“Music fills the world with happiness
plenty sweetness and togetherness 
Music have no friends or enemies. 
Everybody could Dingolay…”

The other essential Shadow songs

Yuh looking fuh horn

Friday evening,
people passing
with box of fried chicken
She watching you
In your old shoe
Feeling to hit you
Somebody will horn you…

Poverty is hell

He gone by the neighbour to beg for some rice
The neighbour under pressure, “Boy, things ent nice.”
He gone in the big shot area to beg
A police put a bullet in his teeny-weeny leg
He gone in the courts and he lost the case
The prosecutor say he have a bandit face

Pay the devil

If you bad, don’t die
Walk about and cry
The Devil down dey
And you have to pay

One Love

Love, to the world
Is all that I can say
Peace, in my soul
I would like to see the day
Of people with, happiness, and togetherness
I would like to see the day
When love would come to stay

The Garden want water

Yuh have the girl, locked up all day
She can’t even, come out and play
Bumsie getting fat like butter
The girl want some manual labour


I’ve spent restless days, And sleepless nights
In many ways, to make soca tight
Now they playing games
Heavy, heavy games
To protect my honour
I going to fight like a tiger

Everybody is somebody

Poverty is what it takes
To make such dangerous mistakes
About who is somebody
But when a woman makes her son
From the time that child is born
He is somebody

Dat Soca Boat

I doing my own thing
Don’t know why they molesting
I am musically sick
Mommy beat me with music stick

Columbus lied

He said he discovered
The whole of America
He never tell nobody
How he had to run from Apache

Updated to note that Winston Bailey passed on October 23, 2018.

Mark Lyndersay

Mark Lyndersay is a photographer and writer living and working in Trinidad and Tobago. His writing about technology is found at TechNewsTT and his photography is here. A long running series of photo essays, Local Lives, considers T&T culture and its Carnival. He has covered Trinidad and Tobago’s Carnival celebrations for the last four decades. He writes a weekly column for NewsdayTT and contributes to Caribbean Beat.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

One comment on “Shadowing The Shadow

  1. adele Oct 23, 2018

    Mark, thank you for such a beautiful and sensitively written article on one of my ultimate favorite Calypsoneons of all time. You made me smile.