This is an antique silverplated loving cup trophy awarded to iconic theatrical actor Monty Woolley (American 1888-1963). Woolley received a bachelor's degree at Yale University, where Cole Porter was an intimate friend and classmate, and master's degrees from Yale and Harvard Universities. He eventually became an assistant professor of English and drama coach at Yale. Thornton Wilder and Stephen Vincent Benet were among his students. He served in World War I in the United States Army as a first lieutenant assigned to the general staff in Paris.[At the age of 50, Woolley achieved a measure of stardom for his role in the 1939 stage play The Man Who Came to Dinner and its 1942 film adaptation. His distinctive white beard was his trademark and he was affectionately known as "The Beard."

This cup is engraved: "To Edgar Montillion Woolley, From, The Taft Dramatic Association, As a Token that they Appreciated, the Importance of Being Earnest, and Skillful in Coaching their Play, in 1912". The cup is hallmarked for the Adelphi Silver Co of New York City.
6" tall with a mouth diameter of 4 7/8". It is 7" across the handles.

Minor surface scratches and some tiny dings. Some wear to the engraving.