Dudley Anderson was born in Jamaica in 1925, and like many other young men in 1944 he volunteered to join the Royal Air Force. He travelled to England, trained, and served as a Medical Orderly. Before being demobbed, he took a bookkeeping and typing course at Wednesbury Commercial College, West Midlands. Dudley returned to Jamaica in 1947, but could not find a job. On hearing of the Empire Windrush’s fare of £28.10s to England, he used some of his RAF bursary to buy a ticket. He described the trip as an excursion with plenty of entertainment provided by the likes of Calypsonians Lord Kitchener and Lord Beginner.
After only a few days at the Clapham Common Deep Shelter in June 1948, some officials from the British Broadcasting Corporation visited there to recruit trainee engineers. He went for training in Cardiff but did not take a permanent job, which involved returning to work in Jamaica. Dudley came back to London and again found it difficult to find a job and accommodation. He worked as a road sweeper for a year, eventually got a job at a telephone company as a fitter, and a room in a hostel in Paddington. He became very frustrated with the housing situation, and decided to save enough money to but his first house in the 1950s in West London.
He worked for the Post Office Telecommunications and for Standard Telecom in London. His last job before retirement was as a security guard at the National Gallery.