1884 – Cuppy was born in Auburn, Indiana on August 23, 1884.
1902 – Cuppy graduated from Auburn High School and went on to the University of Chicago. He was a member of Phi Gamma Delta, acted in amateur theater and worked as a campus reporter for the Record-Herald and the Daily News.
1907 – Received his bachelor’s degree at the University of Chicago.
1910 – Cuppy produced his first book, Maroon Tales, a collection of short stories about the university life.
1914 – Cuppy compiled together a short master’s thesis, took his degree and went to New York.
1918 – After rendering service in World War I as a 2nd Lieutenant in the U.S. Army Motor Transport Corps, Cuppy began contributing to New York Tribune, where Burton Rascoe, a friend was literary editor.
1926 – Cuppy began writing a weekly column "Light Reading" was change to "Mystery and Adventure", for the New York Herald Tribune.
1929 – Cuppy went exile in Jones Island, seeking refuge from the busy life of the city. He was able to finished "How to be a Hermit", a humorous look at home economics.
1949 – Cuppy took an overdose of sleeping pills and died on September 19, 1949, at Saint Vincent’s Hospital. He was cremated and his remains were returned to his hometown and was buried next to his mother’s grave.