Ever the sharp-tongued extrovert, Woolley solidified his social standing by organizing costume parties (including one legendary affair with fifty students dressed as British nobles) and hosting secret champagne bashes at his father's New York City hotel.
Education
Although financially indulgent, William Woolley was also a strict Episcopalian who packed his son off, at age twelve, to the Mackenzie School in upstate New York for a dose of education, piety, and discipline.
Woolley entered Yale College in 1907.
After graduating in 1911, Woolley studied at Harvard but returned to Yale as drama coach from 1914 to 1917.
Career
He spent much of his childhood at the family establishments in Manhattan and Saratoga, where he wore Lord Fauntleroy suits, kept his own ponies, and met Sarah Bernhardt, Lillian Russell, and other luminaries.
There he exhibited the dual tendencies of his life.
On the one hand, he belonged to a "fast set" that included the sons of wealthy businessmen as well as such creative lights as Cole Porter.
On the other hand, he played a key role in Yale's first theatrical flowering, acting in serious productions of William Shakespeare and Carlo Goldoni and directing Cole Porter's brilliant froth at the Dramatic Association's smokers.
He encouraged students to write their own plays, and he staged Tamburlaine and Troilus and Cressida for the first time in America.
The performances were financially successful and consolidated the university's fragile theatrical tradition.
His main independent claim to fame resulted from his portrayal of the crusty Sheridan Whiteside in Moss Hart and George S. Kaufman's play The Man Who Came to Dinner, a role he performed on Broadway from 1939 to 1941 and in a filmed version in 1942.
True to form, Woolley was as well known for his socializing as for his theatrical work.
And he represented a tradition of indulgent, escapist sophistication at odds with the experimental and proletarian styles typical of so much theatrical production between the world wars.
[Brief sketches of Woolley are in the yearbooks of the Yale College class of 1911; and New Yorker, Jan. 20, 1940.
An obituary is in the New York Times, May 7, 1963. ]
Religion
During the 1930's his trim beard, "spectacular" personality, and talent for pranks and mimicry gave him entr�e to caf� society from California to Italy.
Interests
Music & Bands
He directed three other Porter musicals in the next five years; and when his friend went to Hollywood in the mid-1930's, Woolley followed.
Connections
He died, unmarried, in Saratoga Springs, N. Y. Although remembered principally as the "Man Who Came to Dinner, " Woolley had a further twofold significance.