Pre-World War II Career
Osborn was born October 26, 1904, in Oshkosh, Wisconsin. He entered the University of Wisconsin in 1923, then transferred to Yale in 1923. At Yale, together with Dwight Macdonald, Wilder Hobson, Geoffrey T. Hellman, and Jack Jessup, Osborn helped publish The Yale Record and was accepted into Yale's Elizabethan Club. After graduating from Yale in 1928, he studied painting in Rome and Paris, then returned to the U.S. and began teaching art and philosophy at the Hotchkiss School in Lakeville, Conn.. He found breaking into the ranks of serious artists difficult, and he soon turned to caricature.
Osborn was in Austria in 1938, working as a tutor, when he was taken to a Hitler rally. His reaction to this event prefigured his famous disgust with mindless obedience and obeisance: "I was sickened and convinced that before us was a demon," he wrote. War seemed to him acceptable, "if that was the only way to rid the world of his evil.". He attempted to join the Spanish Republicans to fight Franco, and later applied to the Royal Canadian Air Force, being turned down on both occasions because of his chronic duodenal ulcer.
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