Oliver worked on the Great Western Railway. Sometime during the 1960s, he ran away for fear of being scrapped his brakevan named Toad. The two were forced to hide between signalboxes and rely on the goodwill of signalmen to pass at safe times. When control got wind of the runaways, they hid in an old quarry branch and had the cutting blocked by rubbish to avoid being spotted by Diesels outside. The runaways decided it was safe to leave at some point, but before they could reach the greener pastures of Sodor, Oliver ran out of coal. Luckily, Nathan And Duck were able to rescue Oliver and hid him. TFC soon found out and arranged for the three to be repaired and painted in Great Western colours. Toad decided to be Oilver And Douglas' brakevan to thank him.
Oliver was then sent to work on Duck's branch line, but became conceited after the big engines gave him their respect in recognition of his adventures and pushed his weight around, prompting several ballast trucks to push him into a turntable well. Oliver received little respect from the trucks after the incident, but got his own back by pulling the ringleader, A Truck, apart. Oliver is now well-respected by the trucks, out of fear they will be pulled apart too.