Winston Bailey better known by his stage name

Stage name

A stage name, also called a showbiz name or screen name, is a pseudonym used by performers and entertainers such as actors, wrestlers, comedians, and musicians.-Motivation to use a stage name:...

 The Mighty Shadow or Shadow, is a calypso

Calypso music

Calypso is a style of Afro-Caribbean music that originated in Trinidad and Tobago from African and European roots. The roots of the genre lay in the arrival of enslaved Africans, who, not being allowed to speak with each other, communicated through song...

nian from Trinidad and Tobago

Trinidad and Tobago

Trinidad and Tobago officially the Republic of Trinidad and Tobago is an archipelagic state in the southern Caribbean, lying just off the coast of northeastern Venezuela and south of Grenada in the Lesser Antilles...

. Bailey was born in Belmont, a suburb of Port of Spain

Port of Spain

Port of Spain, also written as Port-of-Spain, is the capital of the Republic of Trinidad and Tobago and the country's third-largest municipality, after San Fernando and Chaguanas. The city has a municipal population of 49,031 , a metropolitan population of 128,026 and a transient daily population...

 in Trinidad

Trinidad

Trinidad is the larger and more populous of the two major islands and numerous landforms which make up the island nation of Trinidad and Tobago. It is the southernmost island in the Caribbean and lies just off the northeastern coast of Venezuela. With an area of it is also the fifth largest in...

, but grew up in Les Coteaux, Tobago

Tobago

Tobago is the smaller of the two main islands that make up the Republic of Trinidad and Tobago. It is located in the southern Caribbean, northeast of the island of Trinidad and southeast of Grenada. The island lies outside the hurricane belt...

 with his grandparents. He began to sing at a very early age and he wanted to be a singer although his grandfather told him he must be a lawyer.

He won the Road March in 1974 and 2001 with "Bassman" and "Stranger" respectively. He won the Calypso Monarch in 2000 with "What's Wrong With Me" and "Scratch Meh Back." 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. He won the Trinidad & Tobago Humming Bird Medal (Silver) in 2003.

He was the first to win both the International Soca Monarch

International Soca Monarch

The ' competition is an annual dual-contest soca music event, the finals of which are held on every Carnival Friday in Trinidad and Tobago. Contestants in the event may vie for two separate crowns or titles, the International Soca Monarch for uptempo songs, and International Groovy Soca Monarch...

 and the Trinidad Road March

Carnival Road March

The Carnival Road March is the musical composition played most often at the "judging points" along the parade route during Carnival. The Road March title is among the most prestigious titles in Trinidad Carnival. In Trinidad and Tobago the most Road march titles have gone to the Mighty Sparrow and...

competitions simultaneously, a feat he accomplished in 2001 with his song "Stranger".

Hit songs

He has had hits beginning in 1974 such as:

• I Come Out to Play
• King From Hell
• What is Life
• Crazy Computer
• Jump Judges Jump
• Children Ting
• Dingolay
• Poverty is Hell
• Tension
• Pay de Devil
• Snake in the Balisier

He has also done jingles for commercials such as one for the Inland Revenue office of Trinidad and Tobago. Today he is still active but has slowed down.