Wanting to be an artist since childhood, Bascom filled the pages of his school books in the one-room school house he attended with cowboy scenes. His desire to be a cowboy artist was greatly enhanced after seeing art works of the two great icons of Old West art, Charles M. Russell and Frederic S. Remington - both cousins to his father, John W. Bascom (Remington and Russell were both related to Bascom through their mothers, Clarissa "Clara" Bascom Sackrider Remington and Mary Elizabeth Mead Russell, respectively). Both Remington and Russell were artists that spent time in Canada producing art. In the late 1920s, Earl worked on a ranch south of the Sweetgrass Hills in Montana that was once owned by the artist Charlie Russell and only a few months after Russell's death.