Herb Fillmore was taught at the Chouinard Institute of Art where he graduated at the head of his class. Moving to a career as a technical illustrator in a distinguished position at Lockheed, Fillmore excelled in drawing scaled and very detailed figures. He ultimately began working for some Los Angeles’ most notable art studios. He became highly acknowledged after finishing some very significant works. At this time he made the decision to expand his work to include commercial artistry. For over 20 years he freelanced as an illustrator in Los Angeles for corporations such as Mc Donald's and Mattel Toys. In order to be as authentic as possible, Fillmore was known to spend numerous hours studying the details of his pieces before finalizing his work. Fill's (as he was affectionately called) large body of work remains extremely collectable today.