 Raymond 's first job was as " an order clerk in Wall Street " . In the wake of the 1929 economic crisis , he " enrolled in the Grand Central School of Art in New York City " and began working as a solicitor for a mortgage broker . Approaching former neighbor Russ Westover , Raymond soon quit his job and by 1930 was assisting on Westover 's Tillie the Toiler , through which Raymond was " introduced to [ the ] King Features Syndicate " , where he became a staff artist and for which he would produce his greatest work . 
