About Shadowlingo and its Author

This web space is dedicated to the considerable musical oeuvre of the man, Winston Bailey, also known as The Shadow.* It will celebrate the career of this mighty bard, share research on Shadow, and grapple with the questions that Shadow’s music encourages us to ask.

This blog is launched neither by Shadow nor his industry representatives. It is launched by a fan, perhaps a “fanatic,” as I have always been—since before I was blasting British Punk over the hills of Laventille, blaring synthesised New Wave through the halls of St. Mary’s College in Port-of-Spain, wearing out vintage Hip Hop cassettes in Queens, hunting down classic Blues LP’s in Greenwich Village or maxing out my credit card on old Cuban music at Casino Records on Calle Ocho in Miami.

I was listening close to Shadow long before I became somewhat of a Calypso aficionado in my dawning midlife. And since I am certainly not the only one who thinks that Shadow is timeless and transcends genres, that Shadow is a singular genius, I have launched this blog to recognise the master and his devotees in this, OUR own online paddock.

Here we can vindicate, in writing, Shadow’s staunch cult following. There is a method to the ‘musical madness’ and intellectual rigour in the weirdness!

We know that Shadow’s music is at once innovative and timelessly elemental and that his “message,” if we could use so naïve a term, is universal. So we can at least valorise it on this international stage that is the Web.

Besides being an online space that pays humble tribute to Winston Bailey’s prodigious musical project the Shadowlingo** blog will make clear why ‘de Shadow,’  the man at the crossroads is a Musical Master and Natural Philosopher; a Wordsmith,  Trickster and Perennial Outsider; a Living Legend and a National Treasure of the Republic of Trinidad & Tobago.

We don’t need “lunatics in politics” or experts with highfalutin “degrees in stupidity” to concur. But we are glad they too have begun to notice and to credit the brilliance of this dark jewel.

Lawrence Waldron, March 19th 2014

* Some journalists still call him the “Mighty Shadow,” employing one of the standard heraldic prefixes of the 1960s and 70s, but among his fans and his compatriots in the business this formal qualifier fell away almost as soon as it was coined. Notice that the titular “Mighty” does not appear on any of his album or CD covers, because Shadow doesn’t call himself that either. To call Shadow “The Mighty…” would not only be stating the obvious (as I must do above) but would also be locating this Trinbagonian original on a traditional Calypso lineage where he only partially belongs.

**As for the term “Shadolingo” (spelled “Shadowlingo” in this blog’s URL to make the spelling easier to remember) I coined it to denote the rhythmic syllables that Shadow utters in between and after verses, like Shouter Baptist doption or jazz scat, but neither. “Heem tama hoom day, tam tama hal, heem yoom tama hoom day-yao, eeyoom tama hal” (from “I’m Sick” on the album Mystical Moods, 1985). Shadolingo is like the vestigial syllabary of some ancient galactic language accessible to humankind only if they listen very, very closely to nature…or music. It is not like the spoken languages of we tiny men. But it borrows randomly from our consonants, vowels, and diphthongs  so that it might make some part of itself known to us in our time.

  1. merepamphleteer says:

    Kongrats!!!! Shadow, our organic philosopher, deserves no less. Thanks for the foresight in memorializing the work by creating this space for appreciation and critical reflection on his work.


    • Denyse Plummer, composer of the other great “Tabanca,” admonishes us that it’s better to crown a Living Legend than awaken too late to a lost legacy. We aint waitin’ ’til a hero dead to put a crown on dey head.


  2. thanks for this blog. Thought I was alone in my assessment of Shadow as a stream of consciousness philosopher utilizing the calypso art form as his canvass/page/stage.


  3. Thanks, Gerry.

    It is precisely because each one of the “upper level” fans of shadow feels like we’re alone that I launched this blog. I have had people try to make me feel “weird” because I ‘read too much into Shadow’s nonsense.’ They don’t even realize they’re paying me a compliment when they say stuff like that.


  4. merepamphleteer says:

    Yes, Shadow encapsulates what Keith Smith referred to as ‘our native wit and imagination’ and I think Lloyd Best may have said it best, ‘the true casualties of our education–of the schooling which is so central—may not be the poor dropouts but the distinguished successes.’ And we all remember Sparrow’s haunting line, ‘if meh head was bright I woulda be a damn fool”! Indeed, the apex of instinctive wisdom
    Thanks again for fomenting this conversation. I can’t understand why the universities in T&T have not recognized and celebrated the import of Shadow’s work by honoring him. Then again, perhaps, this forum will shame them into action?


    • Well Said. Education in a colony is designed to produce adequate administrators of produce and production, from the clerk to the bureaucrat. But it was never put in place to produce deep thinkers, philosophers and artists. What THEY produce cannot be weighed and sold at the London Stock Exchange. So when the colony gets “independence” those structures for producing column tickers, row counters and paper pushers remain intact and the artist, poet, composer goes unsung.

      I laugh out loud every time I hear Sparrow sing “if meh head was right, I woulda been a damned fool” but it’s always a kind of bitter laugh…because it’s the best brains that the colonial system wanted most, which it siphoned away from contemplation and introspection and taught instead merely how to be clever.

      And even tho dey beat us like dogs to learn in school that Cutteridge’s cow jumped over the moon, since Calypso wasn’t sent from abroad (so how good could it be, right?), we never learned to appreciate the irony, the literary tragicomedy of the cock’s plight in “Cook, Curry and Crow” (post on that song coming soon)


      • merepamphleteer says:

        Indeed, Shadow forces us to realize that ‘their minds are like factories producing misery.’


  5. Dingolay says:

    Great site. I commend the creator who has rendered a great contribution to calypso art form. Thanks.


  6. cardon emmons says:

    At first I characterised Shadow as “the calypsonian of the absurd” as in “theatre of the Absurd”. Some of the lines seem to border on the absurd. At about the same time I was struggling(still am) to fully understand existential philosophy by reading Sartre and Heidigger etc. Then Shadow’s What is Life opened my brain. Wow! He is our existential philosopher. Purists may shudder; Shadow and Sartre together. Sacrilege! If they will only drink at the font of Shadow’s wisdom. There is a line that has been in my head for a while; ” Feet ah never eat and didn’t feed you”( may not be an exact quote). Simplistic or profoundly Philosophical?

    Liked by 1 person

    • But I think you are right on both these, seemingly opposing, points of view. Shadow DOES court the absurd, in the spirit of the great Spoiler (I’m working on a post about this Shadow-Spoiler comparison), but not just for social commentary and plain kicks like Spoilo loved to do. And that’s where that existentialist intellect that you’re talking about comes in. WHY is Shadow so fascinated by the absurd? He’s up to something…He’s trying to do something with this trick…


  7. beck7479 says:

    (ON: “Winston’s Shadow” https://shadowlingo.wordpress.com/2015/01/18/winstons-shadow-a-visual-analysis-of-the-shadow/)

    Going through your Shadow blog made me laugh heartily when I read, “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.’ Finally, I said to myself, I’m not crazy.

    In early 1970s, around the time of the black power demonstrations, I was employed as a street walker and had the honor of meeting and reading Craig’s material. One piece of writing intrigued me and remains with me. Written on one of his tablets was an outline of: “Social Responsibly and its Clauses”. Although I had dropped in and out of the halls of one of the top High Schools, I had never heard anything like that but there I was, a few years after ‘formal’ education, with this “vagrant” exposing and teaching me deep truths. What was even more touching was to witness Craig walking through the streets of POS with his ‘wisdom tablets’ in tow. Oftentimes he would remain stationary at a spot revealing his manifestos for anyone willing to read them. Sometimes I wondered how he was able to anticipate my reading pace for he’d turn the pages slowly almost in sync with my reading. And at the end of the day he’d make his trek, in his zapat/footwear up the Laventille Hills to his dwelling just past Fort Chacon.

    Now, 50-plus years later, to my great surprise, he surfaces alongside a Greek Philosopher, and the King from Hell! This prompts me to no longer think that I’m “way, way, off”…. I have also followed Shadow from his beginnings and vividly remember him, on a big stone in Glen Road, Tobago strumming away on his guitar

    In doing justice to Shadow’s work you have also helped us remember another of our forgotten philosophers. Keep on Shadowing the Shadow. Great job!

    Liked by 1 person

  8. Lawrence Waldron says:

    It is an honour to help bring the memory of old Craig into the cyber-age and an equal joy to talk to people who remember him. He was a sage in a hive of technocrats, bureaucrats and escapist labourers. My story has some similarities with yours. I was wandering the halls of CIC, reading everything in the school library EXCEPT my textbooks and yet even in my rebellious youth, I was not enough of a rebel (like you were) to stop and read Craig’s ‘tablets’ in full. I would grab a little bit and run. This loss has made me vow never to be neglectful like that again – hence the Shadowlingo blog. People might say Shadow singing’ nonsense but many wise people like his ‘nonsense.’


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