At the age of 17 Robert Bailey moved to Canada to become a photographer. After a varied career as a photo lab technician, commercial designer and journalist, he became a medical photographer. During this time he published lithographs of canvases from the Second World War.

His work was noticed by Star Wars creator George Lucas, who invited Robert to work on Star Wars visions. Lucas bought many of his works for himself as well as for actors and crew members.

Among the collectors of his art today are Harrison Ford, John Travolta, Tom Cruise and the late Carrie Fisher. Bailey himself says about his art: "Only through practice can the dexterity of fine pencil work be preserved".