In 1916, he started his career in earnest when he began working with the African Millionaires, a large carnival group consisting of about 25 members.

His 1939 composition "He Had It Coming" was a hit for Louis Jordan and Ella Fitzgerald under the new title "Stone Cold Dead in the Market".

Gaining a good deal of recognition, Houdini wasted no time in organizing high-profile calypso festivals and concerts around New York, quickly becoming a respected member of the Caribbean communities there.

After moving to New York (as one of the earliest Trinidadian émigrés), he was often the object of derision by the calypsonians still in Trinidad, who claimed that he was stealing their ideas and capitalizing on them in the USA.

Towards the beginning of the 1950s he played regularly at the Caribbean Club on Seventh Avenue, New York, with his only real rival, The Duke of Iron, also a native of Trinidad.