Winston McGarland Bailey, HBM, DLitt (4 October 1941 – 23 October 2018), better known by his stage name The Mighty Shadow or Shadow, was a calypsonian from Tobago.
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Calypso Rose
Tobagonian musician; Calypsonian
1
Black Stalin
Trinidadian calypsonian
2
Crazy
Trinidad and Tobago calypsonian
3
Lord Kitchener
calypsonian
4
Superblue
Trinidad and Tobago musician
5
Singing Sandra
Trinidadian calypsonian
6
Lord Melody
Trinidad and Tobago calypsonian, songwriter
7
Mighty Sparrow
Grenadian musician
8
Lord Pretender
Trinidadian musician
9
David Rudder
Trinidad and Tobago musician
10
The Mighty Duke
Trinidad and Tobago musician
11
Red Plastic Bag
Barbadian singer
12
Ras Shorty I
calypsonian/composer/soca musician
13
Mighty Terror
Trinidad and Tobago musician
14
Mighty Striker
musical artist
15
Fay-Ann Lyons
Trinidadian recording artist
16
Chalkdust
Trinidad and Tobago musician
17
Mighty Cypher
Trinidadian calypsonian
18
Byron Lee and the Dragonaires
musical artist
19
Destra Garcia
Miss Bacchanal
20
Lord Intruder
Trinidad and Tobago musician
21
Lord Brynner
musical artist
22
Lord Mouse and the Kalypso Katz
23
Gypsy
Minister of Community Development, Former- Minister of Arts and Multiculturalism & Calypsonian
24
Mighty Gabby
calypso musician
25
Roaring Lion
calypsonian
26
Sundar Popo
Trinidad and Tobago musician
27
Drupatee Ramgoonai
Trinidad and Tobago musician
28
Mighty Dougla
Trinidadian calypsonian
29
Anslem Douglas
Trinidad and Tobago musician and composer
30
Young Tiger
Trinidadian calypso-jazz crossover performer
31
Wilmoth Houdini
Trinidad and Tobago musician
32
Sam Manning
Trinidad and Tobago musician
33
Mighty Panther
musician
34
Lord Invader
Trinidadian calypsonian
35
Heeralal Rampartap
Trinidad and Tobago musician
36
King Short Shirt
Antiguan musician
37
Arrow
calypso and soca musician
38
Leslie "Teacher" Palmer