Monty Woolley was born to privilege in New York's Bristol Hotel, an establishment owned by his wealthy father. Growing up in the highest of Manhattan's society circles, the young Woolley was well acquainted with many of the famed personages of the era. At Yale, Woolley's classmate and best friend was the equally well-connected Cole Porter; the two chums formed a thriving theatrical/social clique, which resulted in several wittily assembled student musical reviews. Woolley became president of the Yale Dramatic Association, then transferred to Harvard, returning to Yale after graduation as an English instructor. 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. Cole Porter helped Woolley break into professional theater by securing him work as a stage director in the 1930s. Sporting a full professorial beard which emphasized his inbred snobbish intellectualism, Woolley was an ideal "type" for films. After a few years of minor movie roles as doctors and judges, Woolley attained full stardom as the spectacularly insufferable Sheridan Whiteside (a character based on critic/raconteur Alexander Woollcott) in the 1939 Broadway production The Man Who Came to Dinner. He re-created the role for the 1941 screen version of Dinner, then spent the rest of his career playing bombastic variations on Whiteside. When Woolley felt like it, he could be an actor of great range and depth; he was Oscar-nominated for his performances in The Pied Piper (1942) and Since You Went Away (1946). In the 1946 Cole Porter biopic Night and Day, Woolley played himself, and who cared that he was a bit long in the tooth for a Yale undergrad? Though he professed to despise radio, Woolley spent the 1950-1951 season starring in the radio sitcom The Magnificent Montague, portraying a once-famous Shakespearean actor reduced to hosting a simpering kiddie show. Almost exactly the same person offscreen as on, Woolley delighted in insulting and patronizing everyone who crossed his path -- just as much as they probably enjoyed being insulted and patronized. Forced to retire from acting due to ill health, Monty Woolley made his last screen appearance in Kismet (1955), playing an uncharacteristically amiable Omar Khayyam.