Helping to spark a renaissance of the calypso genre in the 1940s and '50s, Lord Beginner recorded and toured in New York with other leading members of Trinidad's "Old Brigade" of calypsonians, before emigrating to England with fellow calypsonians Lord Kitchener (Aldwyn Roberts) and Lord Woodbine (Harold Philips) in 1948. The pair arrived near London on the Empire Windrush, the first of many voyages conveying West Indians wishing to start a new life in Britain. Beginner began playing clubs throughout London and was a success, recording for the Parlophone label in 1950.
Lord Beginner signed a recording contract with Parlophone in 1950. Two of Lord Beginner's more well known calypsos were "Victory Test Match" including the lyrics "Cricket, lovely cricket, at Lord's where I saw it" and "General Election". The first song was reputedly devised on the spot following the West Indies cricket team's victory against England at Lord's in 1950, inspiring Beginner and Lord Kitchener to begin a musical march from the ground to Piccadilly followed by dancing spectators. "General Election" was inspired by Clement Attlee's victory in the 1950 British general election.