Born in Trinidad and working mainly in the United States, he was renowned for his bawdy humor, crisp diction, and confident vocal mannerisms.

Anderson was born in Port of Spain, Trinidad, and in 1923 moved with his family to New York, where in 1927 he married Clarice McDowall, a native of Saint Vincent.

[7] The Duke of Iron recorded singles and albums for a variety of labels, including Decca; Virgin Isle–Supertone; Varsity; Paragon; Stinson and Folkways (owned by Moses Asch); Monogram; Prestige/International; and RCA Victor.

He made many recordings in the 1940s for the Monogram label, including "Marry a Woman Uglier Than You", which inspired Jimmy Soul's 1961 chart hit "If You Wanna Be Happy", and the ribald "The Big Bamboo".

[2] He was notorious for humorous, ribald calypsos, like "I Left Her Behind For You," "Miss Constance" ("she said: I may be small, and yet/I can take on any runner when the track gets wet"), "The Naughty Fly," and "The Postman" (who has "the longest route in town/they know he rings the bell whenever he comes round").