A year later, James arrived in the WWF as "Double J" Jeff Jarrett's 'Roadie'. After a year of being in JJ's shadow, Jesse finally began wrestling, first in tag matches with Jarrett.

He was beginning to receive a bit of a push, with wins over Bob Holly and the 1-2-3 Kid, when Roadie and Jarrett left the WWF together because of distaste for their current storyline. The Roadie was to turn on Jeff Jarrett and reveal that Jarrett's song "With my Baby Tonight" was actually Roadie singing with Jarrett lip-synching.

Armstrong hung out in USWA as Jesse James Armstrong for awhile and did a Heavyweight Champion reign followed by winning the tag belts with Tracy Smothers and holding them through the end of the year.

In the beginning of '96, James and Smothers lost the belts to Tommy Rich and Doug Gilbert. They won them back only briefly from PG-13 in February.

James won a tournament to be the first USWA televison champion on USWA's 1000th show in April. He lost the title to Tony Falk in April, but regained it in May.

He lost a loser-leaves-town match to Jeff Jarrett in June, and returned to the WWF as the "real" Double J, Jesse James, and sang "With my Baby Tonight" as he came down to the ring.

In early 1997, The Honkytonk Man offered his services as Jesse James's manager, but smashed Honkytonk Man's heirloom guitar instead. Honkytonk offered his services to Billy Gunn, changing Gunn's name to Rockabilly to feud with Jesse James.