He studied with Robert Henri and William Merritt Chase at the Chase School in New York, and in Philadelphia as a student of Thomas Anschutz at the Pennsylvania Academy of Fine Arts.
He was part of “The Fifteen Group,” students of Henri including Edward Hopper who exhibited together and rebelled against the strictures of the National Academy.
When Henri went to Europe in 1910, he turned his Henri School over to Boss, but when Henri returned, the two had a disagreement, so Boss renamed it the Independent School and continued there as a teacher. From 1922 to 1941, he taught anatomy classes at the Art Student’s League and also at the Parsons School of Fine Art and the New York School of Design for Women.
His lectures on anatomy were much sought after because of his technique of building muscles of plasticine on a full human skeleton with a nude model demonstrating the muscle action.
Beginning 1925, he went regularly to New Mexico. He completed a series of Indian portraits and landscapes that likely included Arizona as he had a reputation for the skill of his desert landscapes. Howard Devree, in a review of the for the New York Times Art Digest, March 1, 1933, wrote that Boss “has succeeded in presenting some of the amazing desert formations, and has produced cloud effects, contours of rock and brilliance of color calculated to cause the dwellers among artificial canyons of steel and stone to raise both eyebrows.” (Dawdy 44-45)
In 1933, he settled permanently on a ranch in Santa Cruz, New Mexico, where he died of emphysema of 1956.
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