Samuels went to the Salvation Army School, Rose Bank Primary and then attended the high school in Highgate, after which he went to the Dinthill Technical High School. He said that his school career at Dinthill offered no scope for the development of his innate dramatic creativity. 

After school he worked as a storekeeper at the Orange River Agricultural Station and then moved to Kingston with the encouragement of his friends. He landed a clerical job at the Water Commission and then took a job in proof-reading at the Gleaner Company, where he stayed for only one day. 

After failing in his attempt to contact well-known theatre personalities, he enrolled in the Jamaica Theatre School from 1971 to1973. While at the University he did odd jobs to earn his keep. 

During his three years at the Jamaica Theatre School, Oliver participated in various productions. His first play was "A Raisin in the Sun", in which he was a voice off stage. His role as "the coolie" in the play "Servant of Two Masters"had the Gleaner critic, the late Henry Milner commenting that he was "labouring under a misconception". This statement made Mr. Samuels even more determined to prove the critic wrong and it also formed the basis of his inspiration to strive for perfection. His popularity however increased when he appeared in his first pantomime "Music Boy". Even Mr. Milner had nothing bad to say about Oliver's character "Moon Drops". In fact, Oliver went on to become one of his favourite actors, getting constant good reviews. Role after role followed and Oliver Samuels soon became a household name. 

Oliver is an avid reader in politics, social affairs and religion. He has appeared in no fewer than 13 pantomimes playing major roles. He has also appeared in more than 30 other productions. Some of his pantomime appearances include"Music Boy", "Queenie's Daughter", "Dickance for Fippance", "Hail Columbus", "The Witch", "Johnny Reggae", "Ginneral B", "The Pirate Princess", "Trash", "The Hon. All Purpose" and "The Dancing Princess". 

He has also appeared in overseas productions such as "The Fight Against Slavery", the British Broadcasting Corporation's television series aired in 1974. There were other BBC productions such as "My Father Son Son Johnson", "Chef" and "Brothers and Sisters". 

Oliver attained another zenith in his very funny television series, "Oliver", "Oliver at Large" and "Large and in Charge". This series established him as one of Jamaica's actor of comedy. An album with the well-known single "Oliver Yu Large" was also produced and has done well on the local and overseas market. 

Oliver Samuels also appeared in the Jamaican soap opera "Royal Palm Estate" produced by Lennie Little-White. He appeared as "Son-Son". He has also appeared in one Italian and two German films. (Source: www.nlj.gov.jm)