Eric Jolliffe was born in Portsmouth. In 1911, his family migrated from England to Perth in Western Australia before moving six months later to Sydneys. Jolliffe left school at the age of 15, where he then spent six years working as a boundary rider, rabbit trapper and in shearing sheds. A visit to a bookstore, while visiting his family in Sydney, led to the discovery of a book on drawing. He afterwards reflected: "I learned to my surprise that art wasn't necessarily a gift divine but a craft that could be studied and worked at". Jolliffe enrolled in an introductory course at East Sydney Technical College, where his teachers commented on his lack of talent. During the Great Depression he worked as a window cleaner, during which time he inundated The Bulletin with cartoons, which they initially rejected. Eventually they began to buy his cartoons and by the beginning of the Second World War he became a regular contributorr. At the end of the war he joined Smith's Weekly but resigned and began freelancing selling his cartoon strips Saltbush Bill and Witchetty's Tribe to Pix magazine. He was particularly fond of "bush" subjects. Another cartoon strip, Sandy Blight, appeared in Sydney's Sun-Herald. In 1973 Jolliffe began publishing his own magazine, Jolliffe's Outback. George Blaikie recalled in 1979 that Jolliffe "had humped the bluey and toiled at all kinds of farm and station jobs. Wherever he went he sketched the minutiae most people failed to see – shacks and sheds, funny old gates and tree stumps they hinged on, bark roofs, billabongs and cows in bogs. Such authentic reference was poured into his gags and he became our most brilliant interpreter of the countryside."
Australian Aborigines figured largely in Jolliffe's work, including in his numerous pen and pencil portraits in Witchetty's Tribe. Jim Hodge observed that "sensitivity without sentiment describes his approach" and Tony Stephens noted that "Jolliffe made Aboriginal men hunters with a sense of humour" and "the women as beautiful as ... models". Jolliffe's cartoons enjoyed great success with the Australian reading public. Saltbush Bill ran "in Pix magazine for almost 50 years from 1945".