Mighty Shadow

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The Mighty Shadow

HBM (Silver), DLitt
Birth nameWinston McGarland Bailey
Also known asThe Mighty Shadow
Born(1941-10-04)4 October 1941
Belmont, Trinidad and Tobago
Died23 October 2018(2018-10-23) (aged 77)
St. Joseph, Trinidad and Tobago
GenresCalypso, soca
Occupation(s)Musician, singer, record producer, songwriter

Dr. Winston McGarland Bailey, HBM, DLitt (4 October 1941 – 23 October 2018),[1] better known by his stage name The Mighty Shadow or Shadow, was a calypsonian from Tobago.


Bailey was born in Belmont, a suburb of Port of Spain in Trinidad, but grew up in Les Coteaux, Tobago, with his grandparents.[2][3][4] He started singing calypsos at the age of 8.[4]

At the age of 16 he moved back to Port of Spain, where for a time he was homeless while trying to establish himself.[4] In 1970 he performed as part of the chorus in Mighty Sparrow's 'Young Brigade' calypso tent, and by the following year he had begun to establish himself as a calypsonian in his own right.[4] He chose the stage name "Shadow" (he didn't use "Mighty" himself) 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".[3] In his early years he performed wearing all black, with a large hat covering part of his face.[5]

The Guardian newspaper, speaking of Shadow's stagecraft, argued that he had "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", and yet noted that on the contrary his stage presence and music "proved so original, so eerily amusing and so engaging that [he] quickly came to be hailed as one of the greats".[6]

He won the Road March in 1974 with "Bassman" (where he also placed second with "I Come Out to Play") by a record margin, and won again in 2001 with "Stranger", making him the competition's oldest winner.[2] He won the Calypso Monarch contest in 2000 with "What's Wrong With Me" and "Scratch Meh Back".[2][4] His music used bass more prominently than most calypsonians, of which he said "I did 'Bassman', then I started to use melodic bass lines, not like they used before, and when I performed in the calypso tents in the early days, I had one extra sheet of music, just for the bass."[4] Shadow is also known for his unique dance in which he jumped to the tempo of his music in "skip-rope style" with both feet in the air at the same time.[4][7]

He was the second calypsonian to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously, a feat he accomplished in 2001 with "Stranger". He rivalled fellow calypsonians Mighty Sparrow and Lord Kitchener after winning the Road March in 1974.

Shadow is the subject of Christopher Laird's 2017 film King from Hell, featuring concert performances and an interview.[8]

He died on 23 October 2018 at the age of 77 at Mount Hope Hospital in St. Joseph, after suffering a stroke two days earlier.[4][9][10]


In 2003, Bailey received the Hummingbird Medal (Silver) for his contributions to music in Trinidad and Tobago.[11]

On 27 October 2018, 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, an award he had been due to receive before he died.[4][7][12]



  • 1974 - De Bassman
  • 1979 - Love Lite
  • 1979 - If I Coulda I Woulda I Shoulda
  • 1980 - Shadow
  • 1984 - Sweet Sweet Dreams
  • 1984 - Return of De Bassman
  • 1987 - Raw Energy
  • 1988 - Dingolay
  • 1988 - High Tension
  • 1990 - The Monster
  • 1991 - Columbus Lied
  • 1992 - Winston Bailey is the Shadow
  • 1999 - Am I Sweet or What?
  • 2003 - No Middle Ground
  • 2003 - Fully Loaded
  • 2000 - Once Upon a Time



Year Title US
"I Need Love" 77
"No Better Love" 72
"Mystery Dancer" 68
"Hot City" 75


  1. ^ Devers, Sean (24 October 2018), "T&T Calypso icon ‘Mighty Shadow’ dies at 77", Kaieteur News.
  2. ^ a b c "Legendary calypsonian 'Mighty Shadow' dies", Jamaica Observer, 23 October 2018. Retrieved 24 October 2018.
  3. ^ a b Neaves, Julien (2015), "Shadow, the People’s King", Trinidad and Tobago Newsday, 6 December 2015. Retrieved 24 October 2018.
  4. ^ a b c d e f g h i Meschino, Patricia (2018) "Calypso Legend Winston 'Shadow' Bailey Dies at 77", billboard.com, 25 October 2018. Retrieved 28 October 2018
  5. ^ Chapman, Anthony J., & Hugh C. Foot (eds) (1995), Humor and Laughter: Theory, Research and Applications, Transaction Publishers, ISBN 978-1560008378, p. 276.
  6. ^ Mighty Shadow obituary, The Guardian
  7. ^ a b Williams, Lisa (13 August 2018), "Mighty Shadow to be awarded a doctorate by UWI in October", Soca News.
  8. ^ "Curtain call on 2017", Trinidad and Tobago Newsday, 29 December 2017. Retrieved 24 October 2018.
  9. ^ "Mighty Shadow dies at 77". Trinidad & Tobago Guardian. 23 October 2018. Retrieved 23 October 2018.
  10. ^ "Deane, Sandy (2018) "Calypsonian The Mighty Shadow has died", Barbados Today, 23 October 2018. Retrieved 24 October 2018.
  11. ^ "National Awards Database". Otp.tt. Retrieved 23 October 2018.
  12. ^ "The UWI's 2018 Graduation Ceremonies begin October 13". Sta.uwi.edu. Retrieved 23 October 2018.
  13. ^ "Shadow". AllMusic.
  14. ^ "Shadow". Billboard.com.

Other sources[edit]

Further reading[edit]

  • Mason, Peter (1999). Bacchanal!: The Carnival Culture of Trinidad. Temple University Press. p. 40. ISBN 1-56639-663-8.

External links[edit]