A member of New York's gay theatrical society during the Roaring 20s. Woolley was close friends with Clifton Webb and Cole Porter.
A member of the National Guard, Woolley served as an intelligence officer in France during World War I. After the war, he commandeered the Yale Experimental Theater, a position he held until 1927.
Known for his famous whiskers Monty once valued them at $8,000. When Paramount Pictures asked to shave them off for a movie role, Monty asked for $2,000 down and $500 a week for the three months it would take to grow it back. Parmamount declined the offer.
Long-time friend and confidant of Cole Porter stretching back to their days at Yale.
Monty is referred to in Cole Porter's song "Farming" and also served as the witty player of words in Porter's classic "De-Lovely". Monty's favorite song for entertaining at parties was Porter's "Miss Otis Regrets".
Star of NBC Radio's "The Magnificent Montague" (1950-1951).
Woolley was once president of the Yale Dramatic Association.