- Known for his famous whiskers. He once valued them at $8,000. When Paramount Pictures asked him to shave them off for a movie role, he asked for $2,000 down and $500 a week for the three months it would take to grow it back. Paramount declined the offer.
- He appears as a character in a "Look" Magazine mystery story written by Alfred Hitchcock, "The Murder of Monty Woolley", reprinted in Games Magazine in November/December 1980. (1943)
- 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.
- Long-time friend and confidant of Cole Porter stretching back to their days at Yale.
- A member of New York's gay theatrical society during the Roaring 20s. Woolley was close friends with Clifton Webb and Cole Porter.
- He is referred to in Cole Porter's song "Farming" and served as the witty player of words in Porter's classic "De-Lovely". Woolley's favorite song for entertaining at parties was Porter's "Miss Otis Regrets".
- Appears in three Oscar Best Picture nominees: The Pied Piper (1942), Since You Went Away (1944) and The Bishop's Wife (1947).
- He was once president of the Yale Dramatic Association.
- Buried at Greenridge Cemetery. Saratoga Springs, Saratoga County, New York. Plot ANA.
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