He was born Edgar Montillion Woolley in New York City to a wealthy family (his father owned the Bristol Hotel) and grew up in the highest social circles. Woolley attended Yale University, where Cole Porter was an intimate friend and classmate, and Harvard University. He eventually became a professor and lecturer at Yale. Thornton Wilder and Stephen Vincent Benet were among his students.
He left his academic career and began acting on Broadway in 1936. He was typecast as the wasp-tongued, supercilious sophisticate. His most famous role is that of the cranky radio wag forced to stay immobile because of a seemingly-injured hip in 1942's The Man Who Came to Dinner, which he had performed onstage before taking it to Hollywood. In the film, he caricatured Alexander Woollcott, a radio and press celebrity of the 1930s and 1940s. Like Clifton Webb (another larger-than-life personality), Woolley signed with 20th Century Fox in the 1940s and appeared in many films through the mid-1950s. He played himself in Warner Bros.' highly fictionalized film biography of Cole Porter, Night and Day (1946), which left out Porter's very unorthodox professional and personal life.
He was also a frequent radio presence as a guest performer on such shows as The Fred Allen Show, Duffy's Tavern, The Big Show, The Charlie McCarthy Show, and others.
Woolley was nominated twice for the Academy Award, as Best Actor in 1943 for The Pied Piper and as Best Supporting Actor in 1945 for Since You Went Away. He also has a star on the Hollywood Walk of Fame.
Woolley and Cole Porter enjoyed many amusing disreputable adventures together in New York and on foreign travels.
According to Bennett Cerf in Try and Stop Me, Woolley was at a dinner party and suddenly belched. A woman sitting nearby glared at him; he glared back and said, "What did you expect--chimes?" Cerf said that Woolley liked his own impromptu line so much he insisted that it be added to the script of his next stage role.
Woolley lived up to his surname by sported thick facial hair.
