Monty Woolley was born on August 17, 1888, to a hotel proprietor who owned the Marie Antoinette Hotel on Broadway. He was part of Manhattan's elite social circle from a young age and studied at Yale and Harvard, earning a Master's degree from Yale. He returned to Yale as an English instructor and coach of graduate dramatics, where he taught notable students such as Thornton Wilder and Stephen Vincent Benet.
Monty was closely associated with Cole Porter, with whom he collaborated on several Broadway musicals and reviews, including "Fifty Million Frenchmen" and "Jubilee." In 1936, at the age of 47, he gave up his professorship to pursue a career in the theater professionally.
Monty made his Broadway debut in the hit musical "On Your Toes" alongside Ray Bolger. He then began receiving supporting credits in Hollywood films, playing judges, doctors, and other assorted roles in films such as "Live, Love and Learn," "Everybody Sing," "Three Comrades," and "Young Dr. Kildare."
Monty was affectionately nicknamed "The Beard" by friend Cole Porter for his distinguished white whiskers. He was known for his sartorial elegance, ribald sense of humor, and snob appeal. Monty and Porter were prominent carousers in the New York gay social underground.
In the 1940s, Monty came into his own in films, earning an Oscar nomination for his role in "The Pied Piper" and a supporting actor nod in "Since You Went Away." He portrayed himself in the fictionalized biography "Night and Day," starring Cary Grant as Cole Porter.
Monty received top billing in films such as "Irish Eyes Are Smiling," "Molly and Me," and "Holy Matrimony." He appeared opposite Cary Grant, Loretta Young, and David Niven in "The Bishop's Wife" and opposite Thelma Ritter in "As Young as You Feel." Monty ended his film career with the role of Omar Khayyam in the MGM operetta "Kismet."
Above all, Monty will be remembered as the irascible radio personality Sheridan Whiteside in the stage and film versions of "The Man Who Came to Dinner." He played the role of a wheelchair-bound celebrity who wreaks havoc on everyone around him.