Henry Simpkins was born in Winnipeg, Manitoba in 1906 and attended the Winnipeg School of Art under Franz Johnson and Lemoine Fitzgerald. From 1925 to 1928 he was employed by Brigden's Ltd. as an illustrator, working and painting with Fred Brigden, Charles Comfort, William Winter and Walter Phillips. It was during his association with these fellow artists that Simpkins developed his interest in fine art, concentrating on watercolors.

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