Born Edgar Montillion Wooley in New York City, Woolley was a professor and lecturer at Yale University (one of his students was Thornton Wilder) who began acting on Broadway in 1936.

He was typecast as the wasp-tongued, supercillious sophisticate. His most famous role is that of the cranky professor forced to stay immobile because of a broken leg in 1942's The Man Who Came to Dinner, which he had performed onstage before taking it to Hollywood.

He was the life-long companion of Cole Porter - they met while at Yale, and became friends and sex buddies. In 1943 Monty was nominated for Best Actor in a Leading Role award for The Pied Piper, and in 1945 for Best Actor in a Supporting Role Award for Since You Went Away. Woolley has a star on the Hollywood Walk of Fame at 6542 Hollywood Blvd.