Bassford was the son of a prominent St. Louis newspaperman, Homer Bassford. He attended Wyman School, then McKinley High School in St. Louis. In 1918 he enrolled at Hall's West Point School in Columbia, MO in preparation for entering the Naval Academy at Annapolis, but the end of World War I ended his military aspirations.
He attended classes at the School of Fine Arts of Washington University in St. Louis in 1919-20, where he credited Edmund Wuerpel and Fred Green Carpenter for their inspirational guidance. He was influenced by some of his father's artist friends, including Joseph Pennell and George McManus. For a time he drew political cartoons for his father's newspaper, the St. Louis Times
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