By Romeo Kaseram
Winston Bailey (Mighty Shadow) was born on October 4, 1941 in Belmont, just outside Port-of-Spain, in Trinidad and Tobago. He moved to the village of Les Coteaux, Tobago as a young boy, and grew up with his grandparents Evlan and Elly Bailey; mother, Eldris Bailey, also figured prominently in his life. Shadow’s musical education is traceable to the input from his grandfather, who worked during the day as a small-time farmer. However, Evlan was also a choirmaster, and it was from this influence that the young Shadow was taught the rudiments of singing.
As Wikipedia reports, as a young man, Shadow started singing calypsoes when he was eight years old. Imbued with his love for song, his incipient musicality, and an emergent love for calypsos, Shadow began learning to play the guitar at 15. A year later he left Les Coteaux, armed with the lessons in singing from his grandfather, the ability to strum the guitar, and perhaps with a few calypsoes obsessing inside his head. He made the crossing from the small island Tobago to the big-city, big-tent island-world of Trinidad, where he was hoping to establish himself as a calypsonian.
Wikipedia tells us Shadow actually stumbled onto his sobriquet, noting, “He chose the stage name ‘Shadow’ …after coming across some workmen digging a road while he was walking. One of the workmen was in a hole below the road surface and the others were calling him ‘Shadow’, and Bailey said: ‘I felt like they was calling me.’
In his early years he performed wearing all black, with a large hat covering part of his face.” It is difficult to not miss how such an epiphanic call from the underground in the birthing of Shadow’s sobriquet could have led to the formation, enhancement and embellishment, and even his embrace of the chthonic, with its associations of the dark, the underworld, and corollary tropes of madness being contributary, dominant, and atmospheric chords in his successful career.
As Mason notes in The Guardian, Shadow “stood out as an eccentric counterpoint to the colourful norm”. He adds: “On stage, typically clad in dark cape and wide-brimmed black hat, he would perform with a slight frown while either standing still or moving in jumpy, jerky movements as his deep, tremulous voice conveyed a vulnerability that was matched by songs of personal frailty and wild imaginings… It was a persona and outlook that stood in dramatic contrast to the classic bravura of the typical calypsonian, one that might have been expected to generate either bemusement or scorn in his native Trinidad and Tobago. But in fact it proved so original, so eerily amusing and so engaging that Shadow quickly came to be hailed as one of the greats.”
But there were hard days for the young Shadow before the best of times arrived. Life away from Les Coteaux, and in the big city of Port-of-Spain was difficult. Shadow lived in the poorest neighbourhoods of Port-of-Spain, getting by with occasional work as a carpenter. Where his heart was for his music and calypso was not where his talent could find footing, with Shadow discovering it easier to sell his songs to other calypsonians. Caught in the loop where talented young people starting out in life find themselves in the circularity of ability and promise chasing the tail of inexperience, Shadow found himself in the shadows of the stage, unable to convince promoters to give him a break. But this reluctance by promoters was not all due to Shadow’s performativity of the dark, strange, and weird – it appears, as Mason indicates, the young man lacked confidence, and suffered from stage fright.
At his recent funeral Shadow’s son Sharlan shared insights into those formative, early, and difficult days, revealing his father encountered questions such as, “Whey you come from? Just so, you want to tackle Sparrow and Kitchener?” Then, Sparrow and Kitchener were prominent calypsonians dominating both the stage and air. Sharlan relates his father produced the 1973 calypso, ‘Saltfish’, which failed to titillate the public’s appetite. When a dark shadow fell on his ambition to become a calypsonian, Shadow retreated to known rusticity, returning to the comforting nucleus of the Bailey household at Les Coteaux. There he found comforting words from mother Eldris, Sharlan tells us.
Sharlan adds: “Shadow got frustrated. He went down by his mother, and …she was looking out for her son. She gave him a bowl of peas soup. While eating his soup, she said: 'Boy, you see that [calypso] thing in Trinidad.' She love her son. 'Come back and plant peas.' Shadow thought about peas. He didn't backtrack, he didn't put the pen down.” Instead, he returned with ‘Bassman’, and with its lyrics of the confessional capturing his compulsive obsession to overcome, along with its infectious bass-line, Shadow lit up the calypso world with a self-therapeutic hit.
Mason tells us ‘Bassman’ was “about his helpless possession by a hideously catchy steel pan bass-line”. He adds: “Having planned to ‘forget calypso and go plant peas in Tobago’, Shadow finds that ‘Every night I lay down in me bed/I hearing a bassman in me head’. He visits a brain surgeon for help (‘A man in me head/I want him to dead’), but is sent away and has no option but to return to a life of music, revealing to the world the tune that has bugged him so much… It was a strange construction for a calypso, yet it chimed beautifully with listeners – after all, everyone has had some form of bassman in their head – and its dark, if lighthearted, edges of madness and inner turmoil gave an insight into Shadow’s restless, real-life obsession with music. Crucially, and naturally, it also had an irresistible bass-line – one that henceforth encouraged a much greater focus in calypso and soca on what Shadow called the ‘bottom of the music’.”
Shadow was awarded Trinidad and Tobago’s Silver Hummingbird medal in 2003 for his contribution to culture. He passed away last month, October 23, shortly before receiving a Degree of Doctor of Letters Honoris Causa from the University of the West Indies for his contributions as a musical composer, which son Sharlan received in Shadow’s honour.
Sources for this exploration: Trinidad Express; Wikipedia, and The Guardian: theguardian.com/music/2018/oct/30/mighty-shadow-obituary.