Winston’s Shadow: a Visual Analysis of the Shadow

Posted: January 18, 2015 in Uncategorized

From the beginning Shadow set out to be contrary, not only in the content of his lyrics and his innovation of Calypso music but also in his on-stage persona. This article offers a visual analysis of Shadow’s persona—his image—with a few expository detours along the way to sketch the landscape under and behind the shadow that was cast. I owe Winthrop Holder and Dalton Narine many thanks for some fact-checking around the unfolding of events in the 1970s when I was but a wee lad and dem was big man arready. But because there is still a little disagreement among us about certain things, I take full responsibility for any historical errors herein. Thanks Shadow soldiers!


Photo of Shadow’s silhouette by Edward Barrow (detail)

Shadow Takes Centre Stage

In the 1970s, while other Calypsonians glittered in sequins and blinded the audience on Dimanche Gras night with the electric colours of their outfits, Shadow stepped out in black. When trademark dance moves and on-stage hi-jinks ruled the roost, sometimes splitting the sides of the audience in laughter, Shadow stood still, arms at his sides, or fidgeted—only from the knees down—in his patented tiptoe “dance.” If you were lucky, you might see him extend the tiptoe into a full fledged “skip-rope” leap into their air, not quite as high as a Maasai tribesman, but completely vertical, arms still at his sides.[i] Shadow was not just an original, he was redefining the medium: in the studio; on the album cover; and on the stage.

Cloaked in Darkness: of the Sobriquet and the Sartorial

When Winston Bailey was a young fellow, there was an American mystery show on the radio. It was called The Shadow. The protagonist of this show was advertised as a dark, brooding character who stalked the night. Spooky, discordant music introduced each episode of the serial, followed by sinister laughter. Finally the narrator’s voice (in the 1940s, provided by Orson Welles) provided the programme with its signature introduction:

“Who knows what evil lurks in the hearts of men? The Shadow knows.”

The Shadow was described as “a man of wealth, a student of science, and master of other people’s minds”. What impression did this ominous character make on the young Winston Bailey sitting by the radio?

Broadcast of The Shadow episode, Carnival of Death, 1940

Since in the 1930s The Shadow’s disguise—described in broadcasts and illustrated in magazines, published advertisements and other promotional materials in the U.S. and abroad—was a black cloak, with a high collar and a broad, black hat. It would make its way into the persona that the adult Winston Bailey would construct for himself beginning in the 1970s. The liner notes from his first album frankly acknowledge this connection.[ii]

And the very name of the mysterious vigilante, “The Shadow,” seems to be at least part of the mysterious inspiration from which Bailey drew his sobriquet sometime in the late 1960s. For unlike many other Calypsonians, who received their nom de guerre from more senior members of the Calypso fraternity (like receiving a noble title from a monarch), the upstart Bailey selected his own sobriquet—in blatant, Napoleonic disregard of pre-existing hierarchies, hierarchies that saw, for example, Lord Blakie confer on Leroy Calliste the name “Black Stalin,” Commander confer on Kenroy Smith the title “Black Prince” and Lord Shorty, confer on Timothy Watkins the title “Baron”.

But right from the start, Calypsonian Shadow’s persona would begin to evolve, and diverge from the radio vigilante’s on the radio. This was bound to happen. At any given point people are acting as: products of their upbringing and personal history; reflections of their situation in world history and their geographical and cultural locations in the world; and as conscious (and self-conscious) agents of their own analytical outlooks, convictions, inspirations, aspirations and impulses. It can be difficult figuring out your own mind, and which of the above factors are making you do what. This is because these factors act on each other while shaping our behaviour.

With this in mind, the unilateral concept of “influence,” in this case from American radio, seems a bit simplistic (i.e., the concept that an idea comes only from one place, is handed down whole and is preserved by the receiver as if the receiver were a mere receptacle). This is why I would propose that Winston Bailey’s Calypso persona was a shrewd selection from elements of the mystique of ‘The Shadow’ on radio but was a selection mitigated by several other, more local factors.[iii]

After all, in Winston Bailey’s youth, no one became “a man of wealth” (like the vigilante on the radio) by singing Calypso. In fact Bailey has always evinced a particularly ‘bohemian’ purity in privileging artistic creativity over capital gains. And as far as we know, while he always had an interest in science and science fiction, it was never Bailey’s intention to manipulate and “master” other men’s minds. Quite the opposite. He teases men’s minds with mysteries, enigmas, dilemmas, and conundrums. He doesn’t persuade them to confess nor does he bring them to justice. He troubles their conscience and leaves them fiddling with potentially liberating questions; not with restraining handcuffs. So The Shadow’s outward persona, not his modus operandi, seems to be what Bailey selected from the radio vigilante.

On the other hand, long before little Winston ever heard The Shadow on the radio, and long after it went off the air, another dark figure in a long cape and sprawling black hat haunted the Carnivals of Trinidad & Tobago, and haunted young Winston’s imagination: the Midnight Robber.

The Midnight Robber has been an important stock character in Trinidad & Tobago Carnival for about a century.[iv] This macabre character may sport a dash or more of colour in his overall accoutrements, but he often dresses mostly in dark colours, with appliquéd skulls, bones and other symbols of death, destruction and decay, especially on the inside or back of his cape. His broad-brimmed hat may be in the bolero, cowboy, fedora or some other style—as long as the brim becomes a veritable parasol over his shoulders. He blows a whistle to announce his entrance and to punctuate his speeches, and may carry a pistol, or two.


Commentor (Brian Honoré) as the Midnight Robber, O’Cangaceiro

By the 1950s and ‘60s, bands of Robbers could be seen roving together, but “long ago in Tobago, the Carnival wasn’t so.” For the original Robbers from the period of Winston’s youth, on both islands, were solitary figures who seldom spoke to each other.[v] They frightened and berated the Carnival bystanders instead. The Midnight Robber speaks in “robber talk,” a verbose and boastful rigmarole of self-reflexive praise-singing, a deliberate inversion of the griot tradition, which sings the praises of leaders and ancestors (while also carrying the news and reciting the histories). Almost a century before “brag rap” in the Hip Hop tradition the Midnight Robber was singing his own praises in the form of frightful and wicked autobiographies, mythologized self-histories, with Olympic levels of ‘lyrical dexterity’:

I am the voice of the Agent of Death Valley,

From the day my mother gave birth to me

The sun refused to shine

And the earth started to tremble.

Terror hit the city streets.


From the age of one

my toys were cannons and machine guns


…from the age of four

my name was marked with blood stains on every door


…at the age of seven my physical structure

was of steel ribs, iron jaws, and copper bowels…

Excerpt from Commentor’s Robber Talk, featuring the speech of Andrew “Puggy” Joseph, the Midnight Robber known as The Agent of Death Valley

Thus in the costume and the repertoire of the Midnight Robber, we find some other elements of Bailey’s “Shadow” persona, especially that of the bombastic bull in the Calypso china shop that he was to become in 1971, issuing threats to the revered kings of the genre:

I quite agree Kitchener is great

But in ‘71 he must feel meh weight.

If those steelband boys give this tune a little try

Kitchee boy, water in yuh eye!


So tell Kitchener

to prepare for real war.


And tell Sparrow and Blakie

to leave Kitchener to me.

And if they ignore me,

Well it’s licks for everybody.

When Shadow issued his Threat, some people wondered who this cheeky young fellow was. Was he worth watching or a mere ‘mocking pretender’?

Actor, choreographer and scholar Jeff Henry says of the Midnight Robber, “The Robber was a locally evolved character whose focus and thrust indicated a subversive intention in the people of African descent. In their quest not only for a profile, but for a voice in their developing society, the Robber proved to be an effective conduit. The bombast and extreme exaggeration conveyed a hidden anger and resistance to authority. In all its manifestations, a contained powerlessness was evident and deeply understood by spectators.”[vi]

Thus, in 1971, “The Threat,” like a Midnight Robber speech, was the menacing growl of an outsider, the vainglory of the yet-powerless. But in 1974, Shadow would prove he was no powerless pretender, making good on his treat with his monstrous debut album and a double Road March victory (see section, “Steps into the Shadow,” below). And yet for decades thereafter Shadow did not soften his tone. In fact since “The Threat” he has never put down the mantle of the Midnight Robber for very long. From his follow-up album, ominously, Robberishly titled King from Hell to the equally menacing Dreadness (1976) and beyond, he rained earthly and infernal retribution down on the wicked, the coquettish, and the officious alike. On these recordings he echoed the wrathful aspect of the Midnight Robber far more than the righteous retribution of The Shadow on old radio.

And when I bounce up a woman who come out for love

I huggin’ she up like a real turtle dove.

I would make so much love that you won’t realise

All I want is to dig out your eye. 

You tellin’ yourself you pick up a man.

I tellin’ mehself I have one to hang…

—“King from Hell,” 1974

Poverty dread.

Misery dread.

And I was born in them,

So I must be dread.


When a man tough;

Tough, tough, tough,

Man does think instead

Cuz they ‘fraid to dead!


I always cool,

Like somebody fool.

But when man threaten

I does smell [their] coffin.

—“Dread Wizard,” 1979

Young Bailey did not just invoke the physical appearance and lyrical posture of the Midnight Robber. Also attributable to Robber tradition is a precise part of the mystique that Bailey adopted for his Shadow persona. For Bailey’s would not be simply a watcher, and knower and corrector of the evils of men like The Shadow on the radio. He would also be a product of mysterious natural forces, a mystic, a bard, a spinner of a cosmic (not just urban) mythos and ethos.

The Shadow of detective lore cloaks himself in darkness to terrorize evil men. But the Midnight Robber is a product of the darkness, born on moonless nights, when the earth stood still, or trembled; when the other babies were stillborn and deformed! One is reminded of the villain Bain’s speech to that other dark vigilante, Batman, in Christopher Nolan’s third film of his trilogy.

Bain is more like a Midnight Robber. “The shadows betray you,” he says to his caped, blue-blooded rival, “because they belong to me.” And as he is the inverse of the dark, tortured hero, the Midnight Robber is the unencumbered, amoral wreaker of havoc, the nemesis of The Shadow.

So between extrajudicial para-cop, The Shadow, and supernatural villain, the Midnight Robber stood Winston. His legs spanned the X of the crossroads between the righteous and the wrathful.

But he would seek neither to, ‘master other people’s minds’ like The Shadow nor cloud them with “influential spells and supernatural powers” like some Midnight Robbers[vii] but rather to open their minds with questions (see the post “Judges Jump to Conclusions”). Of course, Bailey would turn out to be more than just both or neither Shadow and/or/nor Midnight Robber. He would become something else. Bailey has often been “something else.”

So just as the Shadow radio programme from America was a popular phenomenon of Winston’s youth, informing his choice of a persona, the Midnight Robber was an aspect of his upbringing and cultural history, perhaps predisposing him to mysterious, hypnotic protagonists with whom he might identify. But not everyone would be attracted to such characters. So what in Bailey’s personal history might have shaped his taste for: (a) a hero in black that operates outside the accepted institutions of the realm (like The Shadow); and/or (b) a spectral and grandiose being with mythic origins that stupefies his rivals (like the Midnight Robber)? And what stroke of genius caused Bailey to identify a need in Calypso for such a dark character?

Black Beauty

Black is all colours and none, a colour out of which anything can come, inside of which anything can happen. Black is possibility. Black is infinity.

But in the Judeo-Christian milieu of colonial and “post-colonial” Trinidad & Tobago where Hindus and practitioners of African religions are routinely marginalised (if not chastised) by chauvinists, the colour black carries definite macabre connotations. Shadow’s decision to adopt this as his colour was definitely a conscious move to situate himself as an opposing pole to that of his jolly peers in their shiny, sequinned suits and sparkling jewellery. By choosing this colour Shadow signalled that he had begun his exploration of the language of opposites.

In the surviving African traditions of Trinidad & Tobago, however, black has a somewhat different symbolism than that held at trembling arms-length by the administrators in town or the pale-frocked ladies in the pews. Black is the colour associated with two orishas that we might link very closely to Shadow’s style, his message and the symbolism that he deliberately adopted in his early career.

Black is the colour of the crossroads gatekeeper Eshu (Elegguá), the messenger between the corporeal and spiritual realms and reverser of conditions; and Ogun, the lord of metals, the crafting thereof into tools and weapons, and the patron orisha of blacksmiths, warriors and all manner of craftspeople and technologists. Black is not the only colour assigned to these orishas. While Eshu is symbolised by black in opposition with red or white (as befits his role as Reverser), Ogun devotees often wear black and green. The precise meanings of these colours as symbolic of these particular orishas is kept in secrecy by their devotees but it is not unusual to see green foods on an altar to Ogun, and blacksmiths derive their very name from the colour of metal and the ash and carbon that is part of their fiery art. So we can guess at a partial explanation.

We cannot ignore that there was an intentional racial implication here too as Shadow proceeded to cloak himself in this darkest of colours only two or three years after the beginning of T&T’s Black Power movement. Shadow is not a high-brown fella; is not a ‘red man’ in line with the predominant tastes of Trinidad’s brown-skinned majority. He chose black as a badge of pride in the complexion and the self-evident ethnicity that made him so unlike the Calypso darlings of yesteryear (from Roaring Lion to the Mighty Sparrow) and as a satirical rebuke of the association of blackness with negative states and behaviours.

This engrained, archetypal tendency in ‘the West’ to literally denigrate the undesirable as “black” had been explored broadly and attacked directly by the Mighty Composer in his “Black Fallacy” Calypso of 1970. There was little to say lyrically after this thorough, near encyclopaedic rebuttal of literary characterisations and popular idioms from “blackmail” and “blackjacks” to “blackballing,” and from “black market” and “black magic” to “Black Friday.” So Shadow adopted the visual symbolism of blackness instead. Every time you saw him you would think about this troublesome category and transcend to embracing black.

In the limited gene pool of writers that have tackled Shadow seriously, much has been said about the African aspect of Shadow’s blackness.[viii] But I would offer a caveat in locating Shadow’s colour choice primarily in social constructions of race. While many attribute to Shadow the most African of origins and inspirations, not only based on his rhythms and what I call his recondite syllabic “shadolingo” (the namesake of this blog, spelled with the “w” so people can find it more easily in web searches) but also on the time in Trinbagonian history out of which he emerged, Shadow seldom talks about Africa and race in interviews. He sings about Africa rarely; about race even more rarely and often, only obliquely. Even in his direct interrogation of the Calypso judges in 1999-2000’s “What Wrong?” he never asks about his complexion.

I propose that as a student of nature, a mystic, a cosmic philosopher race is too corporeal and mundane a topic to dwell on for Shadow. Let me propose an even greater blasphemy to the prevailing scholarship that informs analyses of Shadow by saying that Shadow’s music comes out of him, partially through Tobago, and partially through Africa from a place before Africa, before Pangaea, before Earth!

Shadow flows from the dark matter of the astral plane. You can fiddle with his race if you wish. It’s part of him. Like you, I believe it’s part of him that bothers the Carnival judges sometimes (whether they admit it or not). To them, he’s so strange and so…Negro, at the same time.

So then, how do we reconcile cosmic blackness and racial blackness? Yes, that’s where a discussion of Shadow brings us. Did you think we’d end up here—straddling the awesome, infinite universe and the racial treachery of society?

We might consider that the dark chroma of Shadow’s persona was shaped by previous and then contemporary life experiences of the 1960s and ‘70s, and that it provided a corporeal and temporal foundation, a platform from which he launched his probing, questioning, mysterious, joyful experiment in music, poetry, and philosophical thought. As much as it might have said about him at the time of inception (and continues to say), Shadow-blackness, or ‘the Shadow mystique,’ has been a tool for exploration, a device that opens up a universe of ideas from any location. We are fortunate and proud that the location in question has been the island Republic of Trinidad & Tobago.

Steps into the Shadow

In image, thought, lyrics and creative creed Winston Bailey has always been the quintessential outsider. His inspiration, persona, and performance all come from somewhere beyond Calypso’s broad, corporeal sphere. But his geographic origins also lie far outside the typical watershed of Calypso—the cosmopolitan capital city of Port-of-Spain and the hilly catchment surrounding its northern and eastern boundaries. Although he was born in Belmont in Trinidad, Shadow’s mother sent him to live with his grandparents in Les Coteaux, Tobago early in his childhood. Shadow has always considered this village on the western side of Tobago to be his home both historically and symbolically. Now, it might surprise some people—especially those from outside the Republic of Trinidad & Tobago—that the mere fact of being from Tobago would make Shadow an instant outsider or underdog. But suffice it to say that the relationship between these two ‘sister isles’ is…well…complicated.

Tobago is perceived by many Trinidadians as a slow-paced, paradisiacal, somewhat rural (or ‘backward’) and outlying province of the twin-island nation and Tobagonians are seen by some as veritable foreigners in Trinidad. Tobagonians for their part have often felt neglected by government initiatives and policies drafted in Trinidad, seemingly with only that island in mind, have complained about this openly, and have on occasion proposed secession. To some Trinidadians, Tobagonians might as well be Grenadians—and as a matter of fact, I’ve heard some Grenadians claim Tobago as more Grenadian than Trinidadian. Thus, much of the usual ‘xeno-politics’ that clandestinely, subtly or brazenly affect the appreciation, criticism and official judging of Calypsos (at Carnival competitions) by artistes from Grenada to Antigua have also affected Calypsonians from Tobago. Tobagonian Lord Nelson’s 1978 Soca, “Foreigner,” encapsulates the ironies of being othered in one’s own country.

“Foreigner” by Lord Nelson, from the 1978 album Black Gold

Certainly, Trinidad Calypso history is full of revered, naturalized Grenadians especially, such as Small Island Pride and the Mighty Bomber but even they are considered a notch above the ‘foreigner’ status that Nelson describes in his brooding song about Trinidadian regionalism. In short, if you live ‘in town’ long enough (i.e., in the cosmopolitan milieu of the capital), many Trinidadians there will learn to overlook your foreign origins, and even hold you closer than people from the proverbial provinces, including Tobago. City people, after all, are a separate breed onto themselves.

Still, Lord Nelson, Calypso Rose and Shadow among several others have managed to largely overcome these urban Trinidadian biases to be hailed as Trinbagonian national treasures, even as Tobagonians swell with pride every time one of them trounces singers from the bigger island in Carnival competitions.

So coming out of the village of Les Coteaux, in western Tobago automatically made Winston Bailey an outsider to the 1950s and ‘60s Calypso scene. But it was an outsider status he could and would mostly transcend. He didn’t ask the judges “Am I from Tobago or what?” in 2000 either. But maybe that was the other elephant in the room for just a small, stubborn few.

Winston’s country youth in Tobago, minding his grandparents’ animals, observing them closely and even talking to them as children often do left him with a deep fascination with the interior life of non-human creatures, not just a passing allegorical interest as in the case of other Calypsonians of “Sly Mongoose” and “Donkey City” fame. His wayward, sometimes even homeless wanderings during his teenage years along much of the western part of Tobago tested and deepened his resolve as a seeker, one who peers and listens deeply into the rhythms and harmonies of nature.

The nights of that same wayward youth, sometimes spent outside in the un-electrified, starry blackness of rural Tobago seem to have expanded the young seeker’s curiosity to cosmic breadths. The rich folklore of Tobago with its jumbies[ix] and mythic characters like La Diablesse[x], douens[xi], and loup garou[xii] lent an eerie aspect to Winston’s otherwise astronomical enchantment with the night.

After leaving his grandparents’ home where he had picked up some musical training from his grandfather and local musicians, Winston wandered the countryside and continued his musical training mostly on his own (i.e., autodidactically and solitarily)—on the road, in the forest, under the sky. In the process, he became a self-made musician and poet, resolved on becoming a professional Calypsonian. By the time he made his way down to Scarborough and took a boat to Trinidad in the late 1950s, Calypso music was reaching a kind of international crescendo.

In the following decade, what were arguably the waning years of Calypso’s second golden age, Winston learned from the best, first on the radio and then at the Calypso tents. It took him quite a while to gain his footing in the big city, this stoic from the wilderness (some of that wilderness still protected Forest Reserve today). It was during this period that he selected for himself the multivalent sobriquet, “the Shadow,” and started building the Shadow persona. The name was familiar, struck from the dark hero of radio lore. But the persona, as it evolved over the next two decades was at once clever and unfamiliar: clever in its combination of the physical aspects shared by the international, crusading radio hero and the ominous, boastful West Indian anti-hero; and unfamiliar both in how it adapted the shadowy features of those two disparate literary characters to a musician’s persona and in how it seemed neither vain nor self-indulgent like they were.

But Shadow’s initial appearances on stage in the ‘60s met with mixed results: sudden and sometimes unexpected popularity, stage fright, rejection and neglect by organisers and MC’s, self-doubt, a frustrated retreat to Tobago, an audacious decision to return to the Trinidad Calypso business, and eventually the nurturing encouragement from a few in the music business, perhaps most notably, Lord Blakie. It was Blakie who introduced young Shadow to master arranger Art De Coteau.[xiii]

In those early years of the 1970s, laying his hat where he could up in Laventille, Shadow meditated and composed music in the sporadic quiets of the day, but especially in the still of the night. In the studio, the collaboration between Shadow, the ‘farmer boy from Les Coteaux’ and master-arranger, ‘Professor’ Art de Coteau “reinvigorated” Calypso, effectively creating a new music. It is easy to be superstitious about all the ‘coteaux’ in Shadow’s life (‘coteau’ meaning ‘hill’ in French), from his hilly Tobago village home to the name of his most fruitful and influential collaborator, to the hills of Laventille—the crucible of Calypso. Three hills. The power of trinity, triad, trimurti. Zepie papa!

Trigonal zemís from Tobago. These enigmatic ancient objects can be found only in the Caribbean. Thousands of them have been made, mostly in the islands between Tobago and Hispaniola inclusively (i.e., few are found in Trinidad and none in Cuba so far as I know). Their exact functions thoughout the period they were made (from the beginning of the Common Era to the fifteenth century) are poorly understood but they were observed by Spaniards to be placed in the soils of agricultural plots to make the crops grow. The Arawak term zemí or cemí (meaning “icon” or “powerful charm/object”) is the probably origin of our word zepie/seppie, meaning “secret spell or object that enables us to prevail.” Photographs by Lawrence Waldron (Tobago Museum)

Trigonal zemís from Tobago. These enigmatic triangular/conical objects can be found only in the Caribbean. Thousands of them have been made, mostly in the islands between Tobago and Hispaniola inclusively (i.e., few are found in Trinidad and none in Cuba so far as I know). Their exact functions thoughout the period they were made (from the beginning of the Common Era to the fifteenth century) are poorly understood but they were observed by Spaniards to be placed in the soils of agricultural plots to make the crops grow. The Arawak term zemí or cemí (meaning “icon” or “powerful charm/object”) is the probable origin of our word zepie/seppie, meaning “secret spell or object that enables us to prevail.” Photographs by Lawrence Waldron (Tobago Museum)

Shadow and De Coteau, in their binary orbit, took the bottom of the music—the bass—and put it on top like Bernard Odum and Bootsy Collins had done to R&B in James Brown’s bands, making it Funk, and in the heady, subversive Black Power days of Trinidad history, the audience went insane for the reversal, the musical coup. This was a new kind of Calypso, if it was even Calypso at all. It passed through the speakers, down into the earth and pulsed up into our bones before we even heard it in our ears.

The self-named, uncanny Shadow, the mystic from up in Les Coteaux had come from outside and had overthrown the ‘house of music.’ He stepped onto the Dimanche Gras stage on February 24th, 1974, dressed in black with a floppy black hat, and the bass started talking like a guitar in front of and on top of the music. By the time he complained that “Every time I lie down in meh bed, Ah hearin’ a bassman in meh head” the audience could feel the bassman rattling their ribcages, rupturing their cochleas and making their hearts ‘beat mistakes.’ In the legend of that night, the Mighty Sparrow conceded defeat in his own heart and steeled himself for the judges’ verdict. He himself was shocked when they named him Calypso Monarch instead of Shadow.[xiv] The audience was not happy.

Dimanche Gras loss aside, the Shadow had arrived. That same outraged crowd of newly minted Shadowphiles filed out of the stands that Sunday night and returned to fight another day…the very next morning. Hell, some of them never left the Savannah. And by the end of that Carnival Tuesday Shadow had won the Road March, the people’s choice of what they wanted to prance to in their costumes or ‘civilian’ attire. Not only did Shadow’s “Bass Man” win this popular award. The second most-played song was also his, a tune called “Ah Come out to Play,” which captured the reckless abandon of Carnival itself in the vein of Kitchener’s immortal “Margie,”[xv] but in that inimitable ‘Shadow + Art De Coteau’ style.

From 1974 to around 1985, Shadow continued to craft his dark, mystical persona. As the 1970s rolled on, the rebellious young bard in the pink suit on the cover of both The Bass Man and King from Hell albums receded not only into blackness but seemed to disappear under the broadening brim of his black hat. Somewhere between 1975 and 1976, audience members lost sight of his eyes entirely.

And by the end of the decade he had introduced his infamous skeleton costume—a black suit like many of his others, but this one with white, glow-in-the-dark skeleton bones appliquéd onto the front. While skeleton mas is found throughout the Americas from Trinidad Carnival to Mexico’s Día de los Muertos, Shadow’s nightglow skeleton suit was straight out of the new American Halloween catalogue. But it had never been seen in this context before—on stage, singing Calypso! When the spotlights went out and the psychedelic ‘black light’ came on, the recontextualised skeleton was all that was left, dancing skip-rope style under a black hat as the Shadow’s voice rang,

And in de middle of de night,

Jumbies came out in de bright.

They heard de melody,

So they come to jump with me.


“We want Calypso,

Sing more Calypso,

We love Calypso,

Sing more Calypso.


…and if you stop that jam

We make you a jumbie man!

And as the synthesizer and bass of the new sound started to do that thing together—pulsing and buzzing at the same time, the buzzing “bass warm like Tiger Balm”—audiences were mesmerised…electrified…damned near electrocuted.

On the cover of the 1980 album Doh Mess wit meh Head Shadow is pictured wearing the by-then infamous skeleton suit, looking like an off-duty jumbie on his way home from a hard day’s night back at the cemetery (with that inexplicable briefcase!…what’s in that briefcase?!).

Doh Mess Wid Meh Head (1980)

By 1985, if we had been in any doubt at all about the Midnight Robber aspect of his persona, Shadow made it abundantly clear. The back cover of the 1984 album, Mystical Moods, features Shadow with his back to the photographer, with his arms out to display the iconic appliqués and embroidery on his cape. On either side are boiling cauldrons, embroidered in thin, wire-line (i.e., of unwavering thickness, visually echoing Vodun vévés). The cauldrons send snakes of steam into the surrounding darkness of his cape. In the centre of the cape, at the bottom, is a third cauldron with what appears to be much fancier embroidery on its body. And in the very middle of Shadow’s back are the skull and crossbones, above which is a five-pointed star. These are ominous symbols typical of the Midnight Robber, with his claims of occult powers and origins.


While the first decade of Shadow album covers took some pains to help in the construction of his macabre and mystical persona, the next decade was mostly a mixed bag of imagery in which Shadow seemed to be trying on some ‘different hats’ as it were. This urges us to look more closely at the role of the album covers in the construction of the Shadow mystique.

Dark Jackets: Calypso, Album Art, and Shadow

Calypso music is not known for the artistry of its album covers. Some of the worst designed, worst photographed, worst drawn, worst typeset jackets in published music history have hitched their jalopy wagons to some of the best music—Calypso music. Local Calypso publishing has never had a ‘Reid Miles period’ of graphic design like Blue Note did with its iconic album covers of the 1950s and ’60s. So Calypso fans learn quickly that you really can’t judge the Calypso book by its album covers.

The way that an album cover can sit in your lap and fire your imagination as you get into the groove of the music is a beloved, nostalgic and increasingly resurgent pleasure. Record companies have never stopped making vinyl records—with their nice, big, printed album covers—and some have even increased their production in recent years, and not just because some audiophiles have rejected the tinny, hissing timbre of digital ‘if I don’t have a digit for it I’m leaving it out’ music. The sensual experience of the LP, its jacket, its smell, its tactile interface, its collectability are making a bit of a come-back in the age of MP3s. Who would have predicted that?[xvi]

The reasons for the just plain ‘bad’ album covers in Calypso publishing history are myriad, relating to the economics of the local record companies, some of which just come and go; and the seasonality of Calypso itself, a much lamented reality in the business as the Trinbagonian public listens to imported music for much of the year between Carnival and Christmas. Both of these are ‘sustainability’ problems with which Shadow and other Calypsonians for whom images are important have tried to contend.

But another, far more systemic problem affecting the visual marketing of Calypso music in Trinidad (where the records are pressed and the jackets are printed) is the limited pool of creative visual artists with skills and insights to serve the music industry. Note that the charge here is not a lack of ‘qualified’ artists because a lot of people walk around the island with ‘qualifications’ in various arts not directly related to the beloved, revered and institutionally nurtured ‘Festival Arts,’ ‘qualifications’ which some of them got the devil-knows-where. But the pool of visual specialists in Trinidad who think hard and apply sharply honed skills to the production of insightful and expressive album covers has never approached the size to sustain the album-cover, and now CD-cover making business. Another sustainability issue related to Calypso seasonality.

But this points to an even broader problem in the nation, especially in the bigger island of Trinidad, which is expected to be the publishing centre. That problem is the lack of reverence for the visual arts in general. What are some of the reasons for this? I deal with that in the Appendix to this article as not to distract from the discussion of the Shadow persona itself.

With all the historical, social and economic vicissitudes effecting the dearth of trained, inspired and affordable artists for album covers, Shadow managed to get some effective album covers made in the 1970s and part of the ‘80s. Some of these directly participated in the construction of his persona as the dark wizard; others did not. The first two albums, Bassman and King from Hell, while they reflect a professional and typically 1970s style of album jacket design (a la Granville Straker’s un-credited designers in New York?), they contribute nothing to the dark persona Shadow had already adopted for the stage. Rather they seem to ignore it. On these first albums, evidently using different pictures from the same photo shoot by Cecil Wharff, the artiste is featured in a magenta outfit clutching his cerulean-coloured guitar.

But while the layout of the collage elements by Sam Rodney Jr. is a little ungainly on the jacket of Constant Jamin’ (1975), that album was the first to introduce the silhouette of Shadow in his long, black coat and big, black hat. This silhouette would become a kind of emblem, versions of it appearing on several other album jackets, and on 7” singles as a logo. For example, it appears on the front cover of Going Off (1983), hastily rendered by Ming Tung betwixt two moulting trees.

An almost frustratingly dark, poorly exposed photograph is featured on the cover of If I Coulda, I Woulda, I Shoulda (1979) but the image manages to contribute greatly to Shadow’s obscure persona. Just discernible in the darkness is a topless, bespectacled, turbaned Shadow, lighting a cigarette with one hand while holding a vase of cockscombs in the other. Cockscomb is a flower of the global amaranth family (a symbol of immortality in the ancient Mediterranean world) and here with his turban and lit match, Shadow looks like he’s about to use them in some secret ritual.

The early album that makes the most use of classic studio arts (i.e., drawing and painting in this case) is Music Fever, whose Trinidad and Barbadian prints feature two different works of art, one featuring a painting of Shadow in a bed of musical notes, listening to his own heart with a stethoscope and another featuring a drawing of the singer in one of his patented floppy black hats staring into the distance. While the painting on the Trinidad jacket is uneven in its attention to detail, fussing over Shadow’s face but dashing off his exposed arm in the foreground, in a different colour paint no less, the drawing on the Barbados jacket is masterful through and through, energetically executed with an understanding of how to shade things of different textures.

The Trinidad album leaves the artist and designer completely uncredited and I have been unable to find out whether the artist on the Bajan print received any better treatment (an illegible signature is visible near Shadow’s left shoulder). The graphic design on both jackets is competent, the Bajan version featuring a zooming superhero type of font, as is that of If I Coulda, I Woulda, I Shoulda.

Other album covers of the 1970s feature similarly innocuous, sometimes interesting typesetting accompanied by usually poor photography, but the Dreadness album is well-photographed and designed with an interesting spin on the Shadow image. Here the musician looks like some kind of Jamaican rude boy or Cuban revolutionary (in that hat with that cigar) on both the back and front of the jacket. I suspect he’s just being a badjohn from Laventille, and I think that’s my old street in Trou Macacq he’s sitting in over on the flip side. I could be wrong. The three-dimensional-looking font is classic 1970s style for album covers and TV action dramas alike.

But in the top left hand corner of the jacket front is a little cartouche with a silhouette inside it—the emergent logo of the Shadow. It is a black figure in a broad-rimmed hat, so broad that it clears his shoulders and is in fact wider than the figure’s body. This is the unmistakeable profile of the wrathful, dreadful Midnight Robber. The album’s designer, Art Cirillo, has made this “Dreadness” album design in evident consultation with the artiste. A graphic designer who listens to the music, reads the book or understands the language (so he doesn’t put, say, the Arabic letters upside down or the Chinese ideograms backwards) is doing his job of coordinating the design with the content.

In 1981, Joe Smith snapped an interesting photo of Shadow in a long black gown and black skull cap, coming in from the waves like a Shouter returning from a baptism, and with his guitar held over his shoulder like an axe. This is the photo that “PERAZA” makes into the front and back cover of Return of the Shadow. While the print quality of the photo by Caribbean Graphics (Barbados) leaves something to be desired, the selection of this image (i.e., of the mystic coming in from the waters after some musical ritual) for an album with this name is appropriate and generates just that fascination that makes one hold on to the album cover while playing the record. And the choice of typeface (in some kind of Spanish colonial style like you might see in a Mexican frontier town) is also kind of clever, even a little amusing, like the Shadow is in a Western sequel.

I should note that misspellings of Art De Coteau’s name are common throughout these albums, which suggests that a final review by the men in charge of the music did not always happen before press time. The most embarrassing typo is perhaps “Bread Wizard” instead of “Dread Wizard” on the ‘Coulda, Woulda, Shoulda’ album, compelling every writer who ever mentions this infamous song to write a little “[sic]” next to the title each time. I have dispensed with that throughout much of this blog. “I tired, oui.”

Shadow finished composing his dark wizard image on jacket covers around the 1985 Carnival season with the Mystical Moods album (1984), whose back cover has already been mentioned. The front cover features a kind of colourful, rococo combination of painted and collaged landscape that manages somehow to be a bit spooky…in that way that the bric-a-brac in old people’s house can seem a little unnerving. In the centre of the image is a painterly-rendered tree the top of which resolves mysteriously into the head of a giant bird. Hanging from the same tree are unrelated species of strange, collaged fruit: cherries, grapes and berries. One giant fruit also hangs from the right side of the tree, and on it is pasted an image of Shadow in black, causing the curvature of the fruit to seem at once convex and concave. While this kind of rococo collage by Victor Bloise is not my taste and the boxy font for “Mystical Moods” is wholly uncalled for, I can appreciate the cosquelle creativity of the ‘bird-tree with strange fruit’ and consider it an interesting and appropriate image for a Shadow album, especially one of the last with the then-ailing Art De Coteau.

In fact for much of the next decade (i.e., from 1985 to 1995), Shadow’s album covers did not seem as concerned with perpetuating the established macabre persona he had constructed there and onstage in the first decade. The CD Shadow Mania vol. 1 is the only exception with the superb photograph by Abigail Hadeed and graphic design by none other than the future contemporary art giant, Christopher Cozier.


In Abigail Hadeed’s photograph, the penumbral, in-between world of the shadow (a dark thing intimately identified with a person, having a name, but possessing no tangible substance) is pushed further into the realm of intangibility and inscrutability. Hadeed gives us a reflection of a shadow named Shadow, or rather a reflection of a shadowy silhouette of the Wizard.

Otherwise, in this second decade of his career the dark Shadow persona was now a given and was maintained on stage, while the album covers experimented with a variety of ‘looks.’ On the pastel-coloured Better than Ever (1985) Shadow is a bit of a dandy. I can hear the Miami Vice music in my head instead of the Bass Man. On Raw Energy he’s a man about town, hurriedly photographed in the glow of urban lights. In 1987, he dons the broad hat and black gown again for the High Tension cover but now he looks slick with the studio light reflecting in his shades (hey, it was the 80s!). Even his black gown is shiny.

He’s like a black, hooded assassin on the cover of Pressure Point (1988); softens his images back to plain musician for the next few albums; and then returns to overt occult references in 1992 with Moods of the Shadow for the 1993 Carnival season. On this professionally designed album cover a now bald Shadow is photographed by expert portraitist Mark Lyndersay raising his arms like a priest. But his white gown bears appliquéd snakes crawling up his chest—a big no-no in any church I’ve ever been to!—and pasted below his photo on this slickly designed jacket by contemporary artist Steve Ouditt and graphic designer Juliet Ali is a photo of a cock, favourite blood sacrifice of orisha-worshippers.

If we stare at the jacket long enough, we realize that Lyndersay has lit one of Shadow’s hands and has left the other in darkness, fitting symbolism for the Crossroads master. Again, this is art bouncing off the music.

Front cover of Moods of the Shadow, 1992 (Compare with back cover of Mystical Moods above

From 1992’s Moods of the Shadow to 1994’s Enchanted, the hairless Shadow seems interested in inverting the image of the dark wizard, appearing again in white in a watercolour on the latter. While the artist seems to have had some trouble with his features, the image has an elegant storybook quality, incorporating the trope of the twisted tree from albums like Going Off and Mystical Moods. Behind the Merlin-like ‘white shadow’ is an adorned, golden circle, the adornments rendered to resemble low relief sculpture. Houses, foliage and perhaps water are discernible in the stylised patterns thereon but the engraved circle reminds us of the Yoruba sculptures bordering Shadow’s portrait on the Dingolay album of the previous year, designed by Peter Shim. There, the low relief figures were reminiscent of those on an Ifa divination tray.

On Dingolay‘s jacket, lightning strikes the master’s guitar string, a fitting analogy for the electrifying music of this album that had even the children of privilege prancing in the Trinbagonian nightclubs, shouting “Poverty is hell!” But the electricity is also a prompt that the age of electronic graphic design will take over the jackets from here. Just as the music recording was going digital and Calypso and Soca musicians were switching over once and for all to CDs, the graphic designers on the margins were switching over to programs like Adobe Illustrator and Photoshop; for better or for worse.

In the ensuing years, as Shadow grew his hair back, only silver this time, the Shadow album covers have been designed using digital cut-and-paste, and electronic tiling, watermarks, inversions and distortions. The cool tricks have been executed by technicians more skilled with computers than with the principles of design; a common occurrence in the analogue-digital transition phase of the late ‘90s, especially among people with little training in graphic design and the studio arts beyond it (which all inform graphic design in ways that many technocratic graphic designers themselves don’t always understand).

So without much thought, the name of the album goes on top or on the bottom depending on which of these positions you put Shadow’s name in. As for the colours of these CD covers: if you grab a stack of Shadow CDs from the 2000s and fan them out on the table, they will dissolve into a black, brown and silver blur—like so much spilt black coffee. Sophisticated interplays of line, form, composition, colour, value and implied digital textures are evidently not in the range of the Shadow’s jacket designers. He’s the ‘man in black’ right? So let’s just make the album blackish. Simple enough. A mediocre straight jacket outside of whose range are truly bad and truly good designs.

But we can live without those covers, just close our eyes and travel with Shadow’s music. We could dispense with them entirely, put the songs on our iTunes and go down Cedros and just watch the waves with Shadow in our earbuds. But when we’re home, trying to remember how to relax and contemplate in a Morris chair, that’s when we miss good art with good music.

Today, as the revered silver-haired national treasure, Shadow is now that familiar ‘man in black.’ The brim of that hat has narrowed somewhat to the dimensions of a 1960s Mad Men porkpie, not quite a badjohn stingy brim. And under his hat is a watershed of dreadlocks and a lifetime of coming from outside and challenging the authority inside. His 2015 single, “They Sticking,” is another missive to the Calypso authorities. Somewhat self-imitative in the melody and inexpensively electronic in the production, the lyrics of “They Sticking” are as wry as always.

They’ll give me my piece of pie

they only waiting until I die.

They trying to fool me,

like they think I’m stupidee.

They want to read eulogy,

Something they wrote for somebody

“He was a good man, a very good man,

The late man was a great man”

And if you are bad when you alive

and you doing bad things to stay alive

As soon as you close your eyes

They find you good; they start to cry.

It is not strange to hear Shadow consider his own death. He has been considering it in song since 1974, often threatening to strike out from beyond the grave. Every time he takes another spin in the judges’ tails and takes another crack at this plaintive sub-genre of making judges jump he comes up with some fresh, wry lyrics. In “They Sticking,” he has pinned down the moment when some pompous fool will read an insincere, recycled eulogy over his embalmed head…and then shower him with posthumous awards.

He might be a national treasure, faithfully coming out to every venue dressed in his black uniform but the ‘guardians’ of tradition and the gatekeepers of ‘standards’ are still unsure what to do with Shadow, this tradition of one, this species of one. The danger he faces now is in being at once venerated and outcast, like Diogenes with his lamp lit in the daytime ‘searching Athens for an honest man’ or John Craig wandering Port-of-Spain and environs with his cardboard tablets of wisdom, a person whose criticisms ‘hard-head’ people learn to disregard. Ignorance and folly can develop antibodies to wisdom by adopting its language but forgetting its meaning, in a kind of spry, functional senility.

If yuh tired hearin’ Shadow complain. If it seems like Shadow is too concerned with the opinions of the Calypso authorities he so disdains, especially at this stage in his life when he is definitely his own man and has gained respect for sticking to his Midnight Robber guns, I remind you of the importance of institutional patronage in the fostering of the arts and the role that lack thereof has played in the narrow pool of progressive visual artists in Trinidad & Tobago. We have a few LeRoy Clarkes and Dean Arlens, yes, but how many coming up behind them?

A high master of one of the few arts that are institutionally nurtured in T&T who still doesn’t receive the monetary and/or logistical support from institutional authorities, support that would enable him to hire quality musicians, staff and crew to make the music as finely as he possibly can, is bound to be frustrated. Shadow doesn’t need a medal when he’s dead. He needs to make rich, sweet, multivalent, polyrhythmic, polyphonic music NOW! And put out with decent CD covers, insightfully designed and nicely printed! Let us think about the poet-musician for a moment and the vital role he plays in critiquing the institution which he enriches, and upon which he relies in a circuitous, cultural ecology. Let us consider his importance and his delicate equilibrium before just commanding him “Sing boy, sing!” while shooting at his feet!

The silver-haired Shadow might have to draft a plan to frighten the Calypso gatekeepers one more time. But will that spectre signal his exit, like it did his entrance all those years ago?


The Trinidadian ‘Artwinter’ or “Why Trinis Doh Care ‘Bout Visual Art”

These island territories were not founded as colonies that would specialize in cultural production. We were never meant to be islands full of deep thinkers, contemplating our lot in life or our place in the universe. The colonies of the West Indies were founded to produce sugar, cocoa, coffee and other CASH crops, which would be sold at market abroad. And to minimize the costs of material production in a ‘free’ market, the cheapest possible labour was sought—slaves and then indentured workers.

We, the callaloo hoi polloi, were meant to keep our heads down and work those tools, and if we were encouraged to count or read & write at all it was so we could read ledger books and Bibles, the former to make ourselves useful helping the supervisors with their maths, and the latter ostensibly to give us solace (but in a more practical sense to soothe the beast so he would be less savage, and thus less inclined to burn something down).

Carnival managed to slip through the chicken wire that was hammered around our work schedule and our social cycle because that festival, like the religion it was linked to by Ash Wednesday, allowed us to blow off steam, indulge ancient passions and then calm down…before we returned to work, our bestial urges slaked and our need to satirise our situation and the people who kept us in it, satisfied, hopefully for a year or so.

If even the musical instruments we used at Carnival had occasionally been banned at other times (and at other times of the year), at what point in our history were we supposed to indulge any tastes for painting and drawing and fashioning fine or expressive things in archival materials? Some of our neighbours in former Spanish or French colonies might offer a response to this.

Because throughout Latin America and the Roman Catholic Caribbean, in countries like Haiti and Cuba especially, there has never been a shortage of visual artists. This is because the Roman Catholic Church became an important, institutional patron of the visual arts from the very beginning of the Conquest of these Americas.

For over a millennium the Catholic Church has been awash in imagery and has used it in many ways to inspire and instruct the faithful. Art was a tool for evangelising Amerindians and Africans alike and it turned out that they themselves, being comfortable with icons, were quite good at making images and were quick studies in learning the new kinds of art introduced to them by Europeans.

Andrés Sánchez Galque, The Mulattos of Esmeraldas: Don Francisco de la Robe and his sons Pedro and Domingo, 1599. This Ecuadorian painting is done in a style linked to The Quito School of Ecuador and the Cuzco School of Peru, colonial church-established academies originally established to train criollos (i.e., white Creoles), mestizo, then Indigenous artists to paint in the late renaissance and baroque styles of the 16th and 17th centuries. Eventually even African-descended pupils were taught to paint in this localised style of Peru and Ecuador where it was used to paint this work, one of the earliest known Western style portraits done in the Americas. The panting shows the cacique/governor Don Francisco and his sons in European ruff-collared cloaks, Amerindian jewellery and holding spears of either African or European design. Don Francisco can be properly called a cacique because he was descended from escaped and shipwrecked Africans and the Amerindian Ecuadorians of the area nor known as Esmeraldas, still an African ethnic enclave today. The painter, Galque, was of Amerindian origins and so we have a European style painting of Africans, done by an Amerindian.

Andrés Sánchez Galque, The Mulattos of Esmeraldas: Don Francisco de la Robe and his sons Pedro and Domingo, 1599.
This Ecuadorian painting is done in a style linked to The Quito School of Ecuador and the Cuzco School of Peru, colonial  academies established by Christian friars to train criollos (i.e., white Creoles), mestizo, then Indigenous artists to paint in the late renaissance and baroque styles of the 16th and 17th centuries. Eventually even African-descended pupils were taught to paint in this localised style of Peru and Ecuador where it was used to paint this work, one of the earliest known Western style portraits done in the Americas. The panting shows the cacique/governor Don Francisco and his sons in European ruff-collared cloaks, Amerindian jewellery and holding spears of either African or European design. Don Francisco can be properly called a cacique because he was descended from escaped and shipwrecked Africans and the Amerindian Ecuadorians of the area now known as Esmeraldas (still an African ethnic enclave today). The painter, Galque, was of Amerindian descent and so we have a European style painting of Africans, done by an Amerindian.

Today, those of us who study the art history of the Americas regularly confront the irony of the catastrophic, genocidal Conquest and the fertile breeding ground it provided for a veritable explosion of artistic production, with the Church as the main patron. It is perhaps the biggest conundrum we face, the reality of our syncretic, painful (art) history.

But when Catholics ran Trinidad and Tobago, there was barely anyone here! A lot of the Amerindians had been killed off (the rest mostly confined to missions/reducciones) and a few Spaniards and comparably few enslaved Africans eked out a living on relatively modest, sometimes miserable plantations. So the system of patronage, art training and taste-making in the mainland viceroyalties never took root here. And the Catholic French, both white and ‘coloured,’ who arrived after the Cedula de Población in 1783 with all their enslaved Africans in tow to inflate and infuse the Trinbagonian population got here only a few years before the Protestant and Anglican British walked in and took the place over from Governor Chacón in 1797, basically without firing a shot.

Now, the British have always had a lot of beautiful art in their own country, where art is a far more secular and somewhat elite pursuit that has enabled the English to maintain for centuries a kind of nominal competitive parity with the Mediterranean countries. But Protestants are doctrinally aniconic, encouraging no ‘graven images’ in their thousands of often-decentralised churches. So upon the arrival of the British in Port-of-Spain at the end of the eighteenth century, it wouldn’t even have occurred to islands only just freshly stocked with Catholics that institutional patronage of the arts from the yet-newer Protestant bosses was now effectively off the table in Trinidad or Tobago. After all, people had other things to worry about while they were adjusting to British rule, and for the next couple of centuries they always seemed to have yet another thing to worry about before they gave any thought to visual art.

So as Latin America, Cuba and Hispaniola stepped into the nineteenth century and then the twentieth, transitioning all the while from sectarian Church-funded art to the highly accomplished, non-sectarian art of the romantics then modernists (with the benefit of that handed down, church-funded art training) the British colonies managed to produce very little art by comparison. I challenge the reader to consider the Martiniquan family origins and European training of Trinidad’s great nineteenth century painter, Michel Jean Cazabon to either prove or disprove my point. The reader might also go searching throughout the rest of the then British West Indies to find more than a handful of comparable artists.

Michel Jean Cazabon, Laventille View, 1860s

Laventille View (1860s) by Michel Jean Cazabon, Trinidad’s premier landscape and costumbrista painter (i.e., painter of local “types” of people) and one of Trinidad’s few painters of note in the 19th century.

In the British colonial period (when the Afro-Franco-Catholic custom of Carnival was provisionally indulged) if a governor needed a monument sculpted here or there to commemorate some important countryman of his, His Excellency could send abroad for it. Why bother to train local artists? It wasn’t as if that would become their profession, like in Peru or Mexico or Cuba. So like the persisting centuries-old (pre-British) Carnival, its attendant (and often contingent) Calypso music, and the subsequent Calypso publishing business of the twentieth century, visual art production in these Anglophone islands has hardly been sustainable as a year ‘round venture.

And today, the fact that our ancestors in Africa, India, and China (and also France, Spain and the pre-Columbian Caribbean) had lived their whole lives surrounded by, making or interacting with the visual arts (be it sculpture, painting, drawing, calligraphy, adorned pottery or handmade textiles etc) is easily forgotten. The pelau hoi polloi have been habitually, unconsciously trained out of most of our visual art impulse, regardless of our religious affiliations. For over a century and a half we were subjects of a realm in which there was little pictorial or other art being regularly commissioned by church or state. A hundred and sixty-five years is long enough to forget a tradition. So by independence in 1962, we had become a nation of rural labourers and urban bureaucrats, heavy lifters and paper-pushers…fussing over petroleum instead of sugar.

By independence time, we had accumulated some important visual artists from Sybil Atteck to Carlisle Chang. Many of them had brought back their art training from foreign schools, paid for by their families from the growing merchant class who had just enough free time and education to remember the importance of art. Thus the visual arts had become almost exclusively a private sector initiative, an elite pursuit behind gate & fence, a luxury that was free from broad societal value like it had enjoyed back in Asia, Africa, the Mediterranean or pre-Columbian days—although such societally value-less art did provide a plush (continental?) backdrop to the clinking of glasses at the most ‘social’ soirées and shindigs.

It’s not just artists who don’t fit into a nation of technicians and technocrats, accountants and attorneys, bankers and merchants. Philosophers don’t fit either. They too are obscure and elite; envied and ridiculed. Art and philosophy? “How much yuh could get fuh dat?” How much a pound is art, ethics or existentialism on the London Stock Exchange?

Christopher Cozier, Attack of the Sandwich Men, 2004

Christopher Cozier, Attack of the Sandwich Men, 2004

Ironically, even though his is one of the few socially endorsed, though admittedly Carnival-contingent, art forms (i.e., Calypso/Soca) to survive what I call the ‘artswinter of 1797 to 1962,’ Shadow is as much the misfit in this ‘mad society’ as any committed, hard-thinking, hard-working visual artist. He fits in like a bristling Kongo nkisi sculpture or delicate Rajput painting fits on the factory floor. He fits in like a LeRoy Clarke panting fits in at the KFC down Lara Promenade or a Chris Cozier installation fits into the car park at Trincity Mall (although mischievous Cozier might think that’s a cool idea). Just as ironic is the fact that it is African-looking Shadow, often cited for having the most African musical inspirations (see David Rudder’s comment in Jacob, “Shadow: the Uncrowned King”), who is the one that seems to have broken out of the cash-crop shackles to go journeying into solitary, deep thinking about our lot in life and our place in the universe. Weren’t his people brought here to cut bush for free, six and seven days a week an’ t’ing?


[i] Ironically his minimalistic skip-rope dance would become the most memorable dance move of all the Calypsonians.

[ii] “Winston Bailey…adopted the unusual name, Shadow, and…even goes on stage dressed as the famous “Shadow” of serial fame…” (Liner Notes, Bass Man, 1974)

[iii] In the same way we might look into the origins and ‘influences’ on the American radio programme, The Shadow, and find a range of superficial, facile, instinctive and deeply considered selections from the history of literature and visual symbolism.

[iv] Jeff Henry, Under the Mas’: Resistance and Rebellion in the Trinidad Masquerade (San Juan: Lexicon Trinidad, 2008), 81; Ruth West, Caribbean Quarterly, Vol. 36, No. 3/4, Konnu and Carnival—Caribbean Festival Arts (December 1990), 43.

[v] Henry, Under the Mas’, 84.

[vi] Henry, Under the Mas’, 81.

[vii] Attributed to Midnight Robber, Two Gun Crowley in Henry, Under the Mas’, 85.

[viii] For brief but poignant discussions of Shadow in the context of racial blackness, see Bukka Renie, “Shadow: the ‘William Blake’ of Calypso” in Bukka Renie, May 1999,

(Accessed January 18, 2015); and Claire Tancons, “Lighting the Shadow: Trinidad in and out of Light,” in Third Text, vol. 21, issue 3 (London: Routledge, 2007), 330-331.

[ix] Ghosts.

[x] The ghostly temptress.

[xi] Forest-dwelling children (in fact the souls of stillborn, aborted and other children who died before baptism) with large hats and backward feet.

[xii] A night time shape shifter.

[xiii] Debbie Jacob, “Shadow: the Uncrowned King” in Caribbean Beat, issue 16,, (Accessed January 15, 2015).

[xiv] “Shadow: the Man and his Music,” in Tobago News, March 24th, 2011,, (Accessed October 24th, 2011). The Mighty Sparrow is quoted here as having said of Shadow’s performance that night, “I stood there and saw Shadow take the crowd and turn them upside down; he did what he wanted to them. I realised, if I had lost to Shadow, I would have been beaten by a great artiste.”

[xv] I hope to compare these two magnificent Road March gems in a future post.

[xvi] Actually, many people predicted the endurance and renaissance of vinyl recordings, and even after the supposed death of analogue music, the famed Japanese stylus/cartridge maker Yoshiaki Sugano, descendent of a line of expert samurai sword makers and potters, continued his quest to ‘perfect’ the record stylus. After his death in 2002, his sons have taken over the development and sales of Koetsu cartridges. See and

  1. […] the decades, with a fan website dedicated to unraveling the mystery behind his many intricacies. In one of the posts on Shadowlingo, it’s explained in detail how he would mold this adventure character with heavy influences […]


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