His college experience was rather unremarkable. After college Cain worked at several different jobs, each rather unsuccessfully. He studied singing for a time in hopes of becoming an opera singer like his mother, but when he was told his voice was not good enough to make singing a career, he decided to become a writer. Cain returned to Washington College to teach English and math. In 1917, he earned a master's degree in drama from Johns Hopkins University.
Career in Journalism
In 1917, Cain began his journalism career at the Baltimore American as a reporter. Here he met H. L. Mencken, who would become his mentor and lifelong friend. Mencken greatly admired Cain's writing, and later he would publish many of Cain's short stories and articles in the American Mercury. In 1918, Cain began working for the Baltimore Sun, but his career was put on hold when he enlisted in the United States Army during World War I. He served in France and edited his company's weekly paper, The Lorraine Cross, which became one of the most successful publications of the American Expeditionary Forces.
Cain returned to the Baltimore Sun in 1919, where he remained until 1923.
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