After defeating Barry Hardy in a dark match on the August 16, 1994 episode of "WWF Wrestling Challenge", James signed with the World Wrestling Federation towards the end of 1994. He was billed as The Roadie, an assistant to "Double J" Jeff Jarrett, a would-be country singer. He wrestled on several pay-per-views and television shows, but most of his first WWF tenure was spent accompanying Jarrett and interfering in his matches. In early 1995, Jarrett released the song "With My Baby Tonight", which Jarrett claimed he had sung himself. The planned angle was to reveal that it was The Roadie, not Jarrett, who had really performed the vocals on this song, sparking a feud between the two wrestlers. Before this revelation could take place, James and Jarrett suddenly left the WWF following the second pay-per-view on July 23, 1995.