Jack Pumpkinhead first appearance was early on in the series, in flashbacks during the Legends in Exile story arc, where he can be seen among a large group of Fables fleeing the Adversary’s forces. His next appearance took place almost a hundred issues later, in the Fables story The Ascent, where he is on the run from the Nome King’s (now the ruler of a pan-Ozian empire) enforcers in the Fable Homeland of Ev. It is revealed that he was drafted into one of the Nome King’s press gangs, but eventually managed to escape with Bungle the glass cat and the Sawhorse. While sitting in one of Ev's native Lunch Box Trees, Bufkin accidentally saves the group from a couple of "Rumble Tumble Tom's", the Nome King's enforcers. The group joined forces with Bufkin, and went on to appear in the subsequent Fables story arcs, working to overthrow the Nome King.