Jamaicans who experienced “Soca Madness” in rural St. Mary in the 1980s will not soon forget the premiere performance of a calypsonian from Trinidad & Tobago known as Shadow. On a bill in 1987 with Rootsman, Baron, Bally and others Shadow managed to conquer music lovers partial to partying to reggae music.
“He was well loved,” Charles Simpson the promoter of the event said.
“When he performed “Ease The Tension,” “Peter,” “Feeling The Feelings” and “Bassman” they went crazy.”
The latter was his first big hit and the double entendre to the composition endeared audiences to the lyrical humor and poetic interpretation of the calypso.
“The following years I had to bring him back to St. Thomas, Portland, Clarendon, St. Elizabeth and for a benefit concert for Cornwall College. That charity concert was held at the Royal Yacht Club and it was massive. After, the owner of LaRoose pleaded with me to bring Shadow back to the island for the club opening in Portmore.”
Likewise, on reflection, a privileged Brooklyn crowd that witnessed performances by Winston McGarland Bailey at the former roller rink at Empire Blvd. or any of the venues he performed will recall Shadow’s all-black outfitted ensemble from broad-brimmed hat to knee-high, leather boots.
The often caped character presented a serious façade punctuated by rhapsodic calypso that accentuated his mystical strides across every wide stage.
Without a Shadow of doubt he seemed mighty, dark and spirited regularly damning delivering poignant renditions from “Pay De Devil,” “Shift Your Carcass,” “Pimpilumpilum,” and “Dreadness.”
On other occasions, he emerged in a shadowed garb of a skeleton. A black leotard dominated the decorated fabric marked by white skeletal bones that framed his body. As he moved about, black and strobe lights effected an eerie image to create a mystical atmosphere owned only by the Trinadad & Tobago storyteller.
From a dynasty that included mighty men – Sparrow, Kitchener, Stalin – and a handful of rulers, Shadow shoulder to shoulder alongside the elite of the genre. And when he visited the boroughs, a kingdom of loyalists obliged.
He died on Oct. 23 at the age of 77 at Mount Hope Hospital in St. Joseph, after suffering a stroke two days earlier.
According to Herman Hall, his booking agent and publisher of Everybody’s Magazine, “Shadow had not enjoyed good health since 2016.”
On Nov. 14, friends and fans will gather in Brooklyn to pay tribute to the revered poet, composer and philosopher during a memorial celebration slated for Tropical Paradise Ballroom, 1367 Utica Ave.
There a calypso-soca fan base from all regions will converge to salute the Trinbagonian who delivered original compositions and delighted audiences.
Some will likely recall the nostalgia of standing inside a roller skating rink in Crown Heights, the ice skating rink at Bedford-Stuyvesant Restoration Corporation, the arena at Madison Square Garden and numerous mas camps where he casted his spell prior to many Labor Day celebrations.
A few years ago at Brooklyn College, standing room only crowds chorused “Dingolay” as if they were back-up singers to his repertoire.
And requests for a reprise of his telling account of Caribbean history with “Columbus Lied” will probably remain a standout to his might and penning.
For the most part, Shadow was revered for delivering sobering accounts on sociological issues.
Highly regarded by his contemporaries that included Brother Valentino and Stalin, he was well respected by his peers.
Born in Belmont, a suburb of Port of Spain in Trinidad, some would argue that Shadow like Calypso Rose and Stalin hailed from Tobago. They would not be incorrect because there is where he grew up in a place called Les Coteaux.
Along with his grandparents, the youth managed to boast the privilege of being a native of a twin island and actually claiming citizenry as a son of both.
Reportedly, he started singing calypsos at the age of eight. He was the second calypsonian to win both the title of International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with a song titled “Stranger.”
Shadow is the subject of Christopher Laird’s 2017 film “King From Hell” which features concert performances and an interview.
On Oct. 27, the University of the West Indies conferred on Bailey the Degree of Doctor of Letters (DLitt) Honoris Causa for his contributions as a musical composer. It is an award he was due to receive before his untimely passing. Allegedly, on hearing the news of his impending honor he was enthused and gratified.
Shadow’s son Sharlan Bailey accepted the posthumous honorary doctorate.
Shadow’s farewell, on Oct. 30 in Queens Park Oval, Savannah, Port of Spain was attended by Super Blue, Original Defosto Himself, Winston “Gypsy,” Peters, Rawlston Charles, Colin Lucas, Hollis Liverpool AKA Chalkdust, Edwin “Crazy” Ayoung, David Rudder, Anselm Douglas, Ricki Jai, Moko Jumbies, Lutalo “Brother Resistance” Masimba, president Trinbago Unified Calypsonians’ Organization (TUCO) and a myriad of colleagues and admirers who filled the Grand Stand.
In his honor, Shadow’s son Sharlan and granddaughter Iennesha Bailey performed a duet of “My Belief.”
Hailed as a “visionary,” “icon,” “prophet,” some even referred to him as the “Bob Marley of calypso.”
On that date, Hall explained how in 1989 Shadow’s “Everybody is Somebody” emerged a featured track in the movie “Lean on Me.”
Despite an outpouring of love and appreciation for the calypsonian, for¬mer Pres¬i¬dent An¬tho¬ny Car¬mona admonished a specific sector of the society for ignoring the international acclaim Shadow’s mu¬sic contributed to the coun¬try.
“Why can¬not we be hon¬est about our¬selves, why can’t we say Shad¬ow you were wronged by the judges, wronged by those who nev¬er ap¬pre¬ci¬at¬ed the artist in you or the in¬spi¬ra¬tional con¬tent in your mu¬sic? Wronged by those who gave you a Hum¬ming¬bird Sil¬ver when you are wor¬thy of an ORTT,” Car¬mona said.
He proposed a correction by the National Awards Committee to include honoring Shadow with the country’s highest award.
Arranger Leston Paul reportedly summed up the transition saying that Shadow’s death marked an occasion to be recalled.
“It is Road March in (“Bassman”) and Road March out (“Bassman”).
Trinidad and Tobago is much poorer.
We have lost a genius.
May Shadow rest in peace.”
Catch You on the Inside!
