He achieved a breakthrough when he was signed to appear on an Ulster Television show called This and That. (On the labels of the Fontana singles, he is billed as 'Rog Whittaker'.) In the summer of 1962, Whittaker performed in Portrush, Northern Ireland. Shortly afterwards, he was signed to Fontana Records, which released his first professional single, 'The Charge of the Light Brigade', in 1962. For the next three years, he studied zoology, biochemistry and marine biology at University College of North Wales and earned a Bachelor of Science degree while singing in local clubs, and released songs on Flexi discs included with the campus newspaper, the Bangor University Rag. To further his teaching career, Whittaker moved to Britain in September 1959. However, he left after 18 months and joined the civil service education department as a teacher, following in his mother's footsteps. He enrolled at the University of Cape Town in South Africa.
In 1956 he was demobilised and decided on a career in medicine. Upon completing his high school education, he was called up for national service and spent two years in the Kenya Regiment fighting the Mau Mau in the Aberdare Forest. Upon completing his primary education, Whittaker was admitted to Prince of Wales School (now Nairobi School).
