Robert was born in Taber, Alberta, on 21 September 1921. Three years later the family moved to Calgary, where Robert discovered his drawing talents at age six years. During his years attending western Canada High School, he enrolled in art courses to expand on his art talent.
Robert completed his High School; joining the RCAF in summer of 1941, age 19 years.
He completed his trade school at St. Thomas, Ontario, and graduated an airframe mechanic LAC 1, R92818.
Posted to No. 405 [Vancouver] squadron in the summer of 1942, he was assigned to a ground crew working on Handley Page Halifax B. Mk. II aircraft. One of the aircraft aircrew, flying in LQ-E [Easy] serial W1112, requested a nose art name and lady painting. Robert completed the artwork free of charge, featuring a blonde lady named "Easy Elsie" and a red heart for each operation completed.
During May 1944, Robert painted his second nose art; this time on a Canadian built Lancaster Mk. X, serial KB977. The aircraft was also named "Easy Elsie" but completed no operations as the war ended.