Calypso icon Winston "The Mighty Shadow" Bailey has died.

Bailey suffered a debilitating stroke over the weekend.

He passed away at around 3.50 a.m. on Tuesday at the Mt Hope Hospital.

Bailey suffered a debilitating stroke over the weekend.

Veteran calypsonian Weston “Cro Cro” Rawlins, says the calypso fraternity has suffered a huge loss with the passing of Bailey, a calypso icon.

Rawlins, who credited Bailey for his start up in calypso said: “We loss a big one……this is a big one. He was the man alongside Kitchener and Sparrow making hits. Nobody could beat them. We were great friends. Bailey’s passing has left a void but kaiso will never die.”

Bailey has had an illustrious career in music, which spans over several decades.

He won the Road March title with “Bassman” in 1974.

Bailey won the Calypso Monarch in 2000 with “What’s Wrong With Me” and “Scratch Meh Back”.

His influence on the artform has been tremendous.

Bailey was also known for his unique dance style in which he jumped to the tempo of the music in “skip-rope style” with both feet in the air at the same time.

Bailey, who celebrated his 77th birthday on October 4, was days away from receiving his doctorate from the University of the West Indies for his contributions as a musical composer.

He won the Trinidad and Tobago Hummingbird Medal (Silver) in 2003.

In 2001, he was the second to win both the International Soca Monarch and the Trinidad Road March competitions simultaneously with his song “Stranger”.

Some of Bailey’s popular calypsoes include:

1974 - "Bassman"; "I Come Out to Play"
1975 - "King From Hell"
1976 - "Jump Judges Jump"; "Children Ting"; "Carnival Scenery"; "Do Good"; "Beat Dem Drums"; "Ladder of Success"; "Don't"; "Without Love"; "Everybody Is Somebody"; "Treat Me Nice"; "Constant Jammin"; "Shift Your Carkass"
1988 - "Tension"; "Crazy Computer"; "The Garden Want Water"
1989 - "Feeling the Feeling"
1992 - "Dingolay"
1993 - "O What a Life"
1994 - "Pay De Devil"' "Poverty Is Hell"
"Snake in the Balisier"
2000 - "Scratch Meh Back"; "What's Wrong With Me"; "Stranger"; "Yuh Looking for Horn"; "HIV"; "Domestic Violence"