Woolley was born Edgar Montilion Woolley in Manhattan to William Edgar Woolley (1845-1927) and Jessie née Arms (1857-1927) and grew up in the highest social circles. Woolley received a bachelor's degree at Yale University, where Cole Porter was an intimate friend and classmate, and master's degrees from Yale and Harvard Universities. He eventually became an assistant professor of English and drama coach at Yale. Thornton Wilder and Stephen Vincent Benét were among his students. He served in World War I in the United States Army as a first lieutenant assigned to the general staff in Paris.
Woolley began directing on Broadway in 1929, and began acting there in 1936 after leaving his academic career. In 1939 he starred in the Kaufman and Hart comedy The Man Who Came to Dinner for 783 performances. It was for this well-reviewed role he was typecast as the wasp-tongued, supercilious sophisticate.
Woolley signed with 20th Century Fox in the 1940s and appeared in many films through the mid-1950s. His most famous film role, a reprise of his Broadway role, was in 1942's The Man Who Came To Dinner where he plays a cranky radio wag restricted to a wheelchair because of a seemingly injured hip, a caricature of the legendary pundit Alexander Woollcott. The film received a good review from the New York Times. He played himself in Warner Bros.' fictionalized film biography of Cole Porter, Night and Day (1946), and the role of Professor Wutheridge in The Bishop's Wife (1947).
He was also a frequent radio presence as a guest performer, first appearing in the medium as a foil to Al Jolson. Woolley became a familiar guest presence on such shows as The Fred Allen Show, Duffy's Tavern, The Big Show, The Chase and Sanborn Hour with Edgar Bergen and Charlie McCarthy, and others. In 1950, Woolley landed the starring role in the NBC series The Magnificent Montague. He played a former Shakespearean actor whose long fall onto hard times forced him to swallow his pride and take a role on daily network radio, becoming an unlikely star while sparring with his wife, Lily (Anne Seymour), and his wise-cracking maid, Agnes (Pert Kelton). The show lasted from November 1950 through September 1951.
Woolley first appeared on television in cameos, then in his own dramatic play series On Stage with Monty Woolley. He starred in a CBS TV adaptation of The Man Who Came to Dinner in 1954, which he and some reviewers lambasted, and appeared in other televised dramas in the series Best of Broadway.
After completing his last film, Kismet (1955), he returned to radio for about a year, after which he was forced to retire due to ill health.
Woolley was nominated twice for an Academy Award, as Best Actor in 1943 for The Pied Piper and as Best Supporting Actor in 1945 for Since You Went Away. He won a Best Actor award from the National Board of Review in 1942 for his role in The Pied Piper.
His hands and beard were impressed in the pavement of Grauman's Chinese Theatre in 1943. Woolley received a star on the Hollywood Walk of Fame in 1960, officially listed in the "Motion Picture" category, though his star bears the television emblem.
Woolley died due to complications from kidney and heart ailments on May 6, 1963, in Albany, New York, aged 74. He is interred at the Greenridge Cemetery, Saratoga Springs, Saratoga County, New York.
Woolley and Cole Porter enjoyed many adventures together in New York and on foreign travels, although Porter reportedly disapproved of Woolley taking a black man as his lover. Woolley has been described in scholarly and other works as gay and closeted.
According to Bennett Cerf in his 1944 book 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, "And what did you expect, my good woman? Chimes?" Cerf wrote, "Woolley was so pleased with this line that he insisted it be written into his next role in Hollywood."
In 1943, Alfred Hitchcock wrote a mystery story for Look magazine, "The Murder of Monty Woolley".See America First (1927) - Director
Fifty Million Frenchmen (1929) - Director
The Second Little Show (1930) - Director
The New Yorkers (1930) - Director
America's Sweetheart (1931) - Director
Walk a Little Faster (1933) - Book director
Champagne, Sec (1933) - Director
Jubilee (1935) - Dialogue director
On Your Toes (1936) as Sergei Alexandrovitch
Knights of Song (1938) as His Royal Highness, Albert Edward
The Man Who Came to Dinner (1939) as Sheridan Whiteside