Cuppy graduated from Auburn High School in 1902 and went on to the University of Chicago, where he received a bachelor's degree in 1907. As an undergraduate, he belonged to Phi Gamma Delta, acted in amateur theater and worked as campus reporter for several Chicago newspapers, notably the Record Herald and the Daily News. He lingered at Chicago seven more years as a graduate student in English literature, not showing much interest in his studies, but producing in 1910 his first book, Maroon Tales, a collection of short stories about university life. In 1914 he pulled together a short master's thesis, took his degree and left for New York, where he supported himself by writing advertising copy while he tried unsuccessfully to write a play.
Read Will Cuppy's book, How to be a Hermit, free from Project Gutenberg Australia.