[3] Dobson began singing while a student at Central Branch School in Kingston and at Kingston College, where he sang in the chapel choir, and successfully took part in Vere Johns Opportunity Hour talent contest as a member of The Twilights.
[6] Released by Lyndon and Sonia Pottinger's Tip-Top label in 1959, it topped the RJR charts that year.
[6] Despite his musical success, Dobson kept his job as a salesman and proof-reader for The Jamaica Gleaner.
In 1971, he recorded "That Wonderful Sound" for Rupie Edwards, which sold over 40,000 copies in the Caribbean, and was followed up by the equally successful "Endlessly", which was also a minor hit on the UK Singles Chart.
On 6 August 2011, being the 49th anniversary of the country's independence, the Governor-General of Jamaica conferred the Order of Distinction in the rank of Officer (OD) upon Dobson, for his contribution to reggae music and representation of Jamaican culture.