Calypso’s Shadow: Reworked & Pieced Together

“As long as you can hear music, music is yours, music is very, very special.” — Shadow

The 1984 disco/soca hybrid “Let’s Get It Together” by Shadow is a gem for anyone into exploring odd islander synthesizer experiments. The record was recorded in Trinidad, its two sides mastered by different studios in New York and London, pressed up in Barbados, and now it’s been reworked in Munich — the result of a 4am message from Miami’s Allen Rodriguez, a resident at the Electric Pickle, to Munich’s Lino Rodrigues, a Portuguese transplant who we previously described as a Fort Knox of edits in an interview. Merely internet acquaintances, Lino and Allen do funnily enough share the same last name. Better known to the music world as Alkalino, Lino has recontextualized the record into into a faster, almost techno form more suited for today’s DJs. It’s not the first time in recent years that the songs has seen renewed interest, just last year the Whiskey Barons did a version as part of a repress of the original’s dub mix by Cultures Of Soul Records. The Barons were “asked” to do so and it sort of reflects in the results, not contributing much to the overall vision. It definitely makes sense as a repress though considering that the first pressing of the Sweet Sweet Dreams album that the single was released on shows lustful numbers as far as Discogs is concerned; 1016 people want what only 96 have, and the vinyl marketplace shows you won’t find prices below $100 regardless of the domestic (if any of the very first Shadow Records pressings are even on sale) or import release. The special US dub version on Kaliko Records graces upwards of $250.

If one were to look into the backstory of the charismatic Shadow, born Winston Bailey, they’d be exposed to a perplexing character that the traditional calypso world has had no clue what to make of. Dig deep enough and it becomes clear his contributions to calypso were comparable to Frankie Knuckles’ impact on house or Juan Atkins’ influence over techno. In a 1989 interview with Trinidad newspaper the TnT Mirror, Shadow explained his contributions to calypso as such, “My music is characterized by a lot of energy, because of my emphasis on the foot drums and bass…” Shifting focus and priority to these very same elements is what would solidify Chicago house and Detroit techno as their own distinct evolutions in dance music, with house expanding upon the Philly Soul sound by adding drum machines and synths while techno took its inspiration from the robotic Kraftwerk, only ratcheting up the funkiness — granted both were working with a lot more moving parts than any one reduction.

For those paying attention, Shadow is credited with godfathering in soca, in its so (soul) + ca (calypso) sense, and the genre is largely what his body of work has fallen under, although he’s always been an outsider. Ahead of his time, the significance of this was overwritten by the popular, but confused, narrative. Bukka Rennie certainly depicts Shadow as an enigma when he writes about him, “He copies no one, he imitates no one, he composes like no one before and like no one ever will, he is completely and totally original in his thinking, his way of seeing and his way of articulating.” Much of his work is looked over as simple by critics, but it’s in his economical use of words, carefully spending each one, that his charm and complexity — often what’s left unsaid — really lie. In the fiercely competitive and hotly debated world of calypso, his eccentricities have not always played well with the status quo.


Shadow's 1979 record ”Dat Soca Boat” was a witty response to the ”soca“ controversy.

Not only artistically, but geographically Winston Bailey didn’t quite fit the mold of the other calypso kings that he dreamed himself joining the ranks of. He was born in Trinidad, but spent his childhood on its more rural sister isle Tobago, staying with his extended family and tending animals in Les Coteaux. As a farmer boy from the bush, his Tobagonian upbringing instantly placed him outside of the admittedly Eurocentric — ironic, then, that today one of his comparatively overlooked singles is being reworked through the European lens — aspirations of the Trinidadian cosmopolitan capitol city Port of Spain, and subjected him to its cultural biases of upholding a certain pedigree of calypsonians. Perhaps in both his music and his looks, his blackness and Afro-informed fusion of styles did not sit well.

Already breaking with tradition, Bailey bucked the conferring of titles from one calypso royalty to another and adopted a dark horse mentality, coming up with his own sobriquet of Shadow — which he has also always chosen to forego the customary designation of “Mighty.” The name was literally a natural calling for Bailey, he himself recalls hearing someone being called by the name of “Shadow” and feeling like the person was addressing him. It’s hard to tell if his persona was the root cause of the rough trajectory of his career or if, through some mystic insight, he had preordained what his experience would be; was he too innovative, too African, or harboring too much of a chip on his shoulder? Whatever the case, the calypso world at large kept him at a distance, yet, much like the real thing, one may try and psychologically run from it, but a shadow is never physically far behind. As for this particular Shadow, he’s certainly hard to pin and full of increasing intrigue should anyone attempt to shine a light where it doesn’t belong. In a rare TV interview with Calypso Showcase, the interviewer says, “We almost didn’t know what to cut out as far as Shadow was concerned.”

According to the liner notes on Winston Bailey’s first album, inspiration for the identity also came from listening as a youth to a radio incarnation of the serialized drama, The Shadow, a broadcast that would open with the introduction, “Who knows what evil lurks in the hearts of men? The Shadow knows!” This crime fighting vigilante figure with uncanny abilities was a predecessor of the superhero. Like The Shadow, Bailey has become somewhat of a cult hero in his own right over 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 from one of the most discriminate and heavily favored characters during Carnival, the agent provocateur of the Midnight Robbers. A major part of the Midnight Robber tradition is the costume, robbers stand out from the colorful surroundings of Carnival with their black clothes, capes, large brimmed hats, and macabre accoutrements, which would all become visual signifiers of Shadow. He’d also adopt their “robber talk” style of braggadocio rhyming, threatening attitude, and borderline supernatural capacities (similar to, but predating the kind of boasting later found in rap).

It’s funny, then, that on the Dimanche Gras night in 1974, he himself was robbed. Extremely evident, even through the curious eyes of a child, the stripping of the title from Shadow was captured by an anecdote preserved in the Rolling Stones’ coverage that year. “And outside the TV shop, the little kid in pajamas turns his back on the replay of the Sparrow’s coronation and sets off bopping down the street with his empties, yelling, ‘The Shadow was robbed!'”

Carnival is a massively hedonistic affair, just look to some of the poignant descriptions of it in the Rolling Stones piece and one would be amiss not to see the parallels between it and their favorite electronic music gatherings. In that ’74 magazine issue, the Carnival is depicted as a “mob exercise” where “everybody gets wired up on rum and Carib beer and ganja and most of all the sheer ecstatic tribal delirium of being there, and they all jam the streets, tracking their favorite bands and jumping-up — just generally leaping and jumping and dancing till you drop.” Later, writer Michael Thomas goes even further in highlighting the religious resolve of the revelers. “By now, they’re staggering on their feet, some of them, suddenly convulsed by a sharp spasm, their eyes rolled back, their limbs twitching. They haven’t slept for days, they’re running on rum and Coca-Cola and the beat of the drums, and they can’t stop now because if they did they’d seize up and splinter. And they’ve still got two days to go.” Memories of the tabloid-like media frenzy surrounding the acid house explosion during the reign of Thatcherism in England come to mind when he speaks of the Carnival’s historical early days. “It was all too pagan and high spirited and it scared decent people half to death.” Finally, we all have those stories of that overindulgent member of the scene that’s eventually, to repurpose a house classic, too far gone and with no way back. “A few manic ecstatics get so carried away they can’t speak for weeks, one or two burn out altogether — they forget their names, some last thread snaps, and they can be found weeks later, lurking in doorways…”

This is Shadow's 1974 hit ”Bass Man,“ which won him the Road Monarch.

As a folk-based music in the griot tradition, calypso has always been the people’s music, and at that Carnival in 1974 Shadow was unanimously considered to be the favorite, winning the Road March competition, determined by sound trucks and steel bands, with both the 1st and 2nd place accomplishments of “Bass Man” and “Ah Come Out To Play.” This alone involved years of struggling to make it onto any tent stage during Carnival Season — since the age of 16 — and the many ups and downs whenever he finally did. At one point he was even relegated to ghostwriting for other calypsonians, earning them encores while he still couldn’t make it no matter where he tried. As Shadow said in a feature with Caribbean Beat later in life, “I was always good for the people, but I couldn’t please the judges.” The lyrics to “Bass Man” even open with Shadow singing, “I was planning to forget calypso, and go and plant peas in Tobago.” The problem? A bassman from hell who would not let him quit singing, haunting him in his sleep, a poetic injustice of creativity’s possessive spirit and a common plague to many an artist. So, after three years of different versions of “The Threat,” directed at untouchable tyrant calypsonians the Mighty Sparrow and Lord Kitchener (who had the Road March title in a stranglehold for eleven years), Shadow had finally delivered on his promise to overtake the reigning kings — at least as far as the streets were concerned. The less easily moved and more critical moment of judgement during Carnival comes in the form of the Calypso Monarch title though, awarded for the best songwriter each year. Finalists’ performances are showcased on the national stage — to a predominantly middle class live audience due to ticket prices — at the Queen’s Park Savannah the night before the more public-facing Carnival kicks off. Sanctioned by the government, it institutionalizes the patronage of calypso artists as Trinidadian national treasures (or not), meaning it suffers from a purist unwillingness to bend or change and an overt classism.

”Doh Mess Wid Meh Head“ is a look into Shadow's struggle with acceptance and contempt for authority.

With the wisdom of age and experience, Shadow has said, “Judges don’t worry me too much. They don’t try to understand. They remain in the past. They have to understand everything is based on change. Anyway, I can’t keep them in my head or else there’d be no place for my music. And I can’t make a tune for them.” But Shadow’s constant struggle with the judges of this competition during his earlier years is well-documented through his own music and songs like the retributive “Jump Judges Jump,” which asked the judges to join him in hell after that painful 1974 defeat. His ’75 album was titled King from Hell, the fiery pits of which he felt forced to resign to if he ever were to take his rightful place as king, albeit now a vengeful one. Subsequent losses would lead to more calypsos on the subject and eventually result in him refusing to re-enter the Calypso Monarch race again for 17 years–not until ’93. During this break, 1980’s “Doh Mess Wid Meh Head” scathingly criticized classism in calypso and its authorities’ reluctance to give him the trophy. “I know why they acting so, I come from the ghetto,” he sang. Shadow frequently spoke on many plights of the world in such a universal way, with the topic of poverty and its effect on the dignity of people ever-present in songs like “Everybody Is Somebody” (1976) and “Poverty Is Hell” (1994). Many people’s belief, including his own, would turn to the hopeless notion that he’d never receive his proper honors, not until he was buried in his grave, but this was not to be the case. It was a long time coming, but Shadow was eventually crowned in 2000, when, after years of tearing down the establishment, he reevaluated his message and shifted the focus towards a place of humility, asking his detractors the question, “What’s Wrong With Me?” The song’s backing vocals would answer the call with “we don’t know,” and the judges searched, but couldn’t find a reason either. He’d take it all home with “Scratch Meh Back,” a song about the indignities of age. Yet, he has aged well with cross-generational appeal and a now legendary status as an anomaly within the world of soca and calypso: a true folk hero.

A live performance of Shadow's 2000 Calypso Monarch winning ”What's Wrong With Me?”

Austen van der Bleek

"The problem is that bad writers tend to have the self-confidence, while the good ones tend to have self-doubt.” — Charles Bukowski... Is Austen a good writer? It’s doubtful. As a DJ he’s been described as “too young to be this deep.” You can find him performing around Florida and representing for Open House Conspiracy.