First encountered in the 14th century in a pub that would one day be in London's East End, Gadling postulated that people only die because it is a bad habit, that it is only done because everyone else does it, and that he would have no part of it. Dream believed that this might be an interesting experiment, and so told Gadling that, if he truly believed the way to live forever is simply not to die, Dream would meet him in one hundred years in the same tavern for a drink.
Gadling agreed and after one hundred years they meet again. At first, when Dream showed up Gadling believed that he had made some kind of deal with the Devil. Dream convinced him otherwise, and they agreed to meet every one hundred years for a drink.
During their meeting in the 1800's, Gadling accused Dream of being lonely and he continued to meet Hob because they were friends, and that was why Death never came for Gadling. Dream was outraged that Gadling would suggest that "one of my kind" needed friends, and stormed out of the tavern.One century later, Gadling was waiting for Dream in the bar. When Dream finally turned up, Gadling admitted that he didn't expect him to show. Dream replied, "I was always told it is bad manners to keep one's friends waiting."
After the current aspect of Dream died, Death visited Gadling at a renaissance fair, and told him that her brother's destruction was not just a dream. Then she asked him if he was ready to go; if he was finally ready to die. After a moment's thought, Gadling replied that he was not ready; he still had so much to live for, and besides his girlfriend would kill him.
After his meeting with Death, Gadling had a dream where he met Morpheus on a beach, and they greet each other warmly. Then a street painter whom Gadling once met, who was in reality another of the Endless, Destruction, joined them, and the three of them walk off down the beach.
Hob is also called Robert, and Bobby over the years. He first appeared in The Sandman: The Doll's House #1 Vol. 2 and remains a recurring character until the end of the series.