Born in Siparia, Tiger was originally a boxer who won the Trinidad bantamweight championship in 1929. He was active in calypso from his teens. He was a member of the Old Brigade of calypso singers, which included Lord Beginner, Attila The Hun, the Roaring Lion, and Lord Pretender. In 1935, he went to New York with Attila and Lord Beginner to record for the Decca label. In 1939, he won the first Calypso Monarch competition with "The Labour Situation in Trinidad And Tobago."
More so than his contemporaries he sang about social and political issues. His best known songs are "Money is King," about economic inequality, and "The Gold in Africa," about the Italian invasion of Ethiopia. Recording together with Atilla and Beginner as the Keskidee Trio, he recorded some lighter tunes, including "Don't Let Me Mother Know."