Actors from the major urban stages of Boston and New York City were drawn to 'Sconset not long after Edward Underhill built his cottage enclave on the south side of town in the mid-1880s. For many, the attraction lay in relief from stifling city streets and the closed theaters of summer in an era before "comfort" air-conditioning became common in the 1920s. According to the testimony of some, it also offered an escape from the prying eyes of the press and the business side of things. Writers; producers; and players in melodrama, comes the, musicals, silent movies, and, later, the talkies, found summer respite there, distinguishing that period in the history of the village.
'Sconset was not disturbed by the sophisticated newcomers, who enjoyed the simple pleasures of life with their families and city friends while contributing their creative and financial support to the community. The little village by the sea offered a picturesque "anything goes" setting for the zany summer antics of the theatrical set
The Fawcett family first summered on Nantucket soon after 1900, as a result of a fellow actor's recommendation. Actors George and Percy Haswell Fawcett, Broadway stars of their day, rented one of the Underhill cottages with their two daughters and grandmother Haswell. George Fawcett later starred in Maurice Chevalier's first American movie, Innocents of Paris. News of the carefree, healthy, and stimulating environment spread, and more theatrical folk joined their colleagues as poor working conditions increased for actors. Frank Gillmore brought his family, including daughters and future actresses Margalo and Ruth. Gillmore was president of the 'Sconset Casino for several years and later was one of the founders of the Actors' Equity Association, which addressed the intolerable practices that had been imposed on performers for many years. Margalo Gillmore was in the cast of High Society in 1956.
The Casino was the summer stage for many nationally recognized personalities, including opera singer and comedian Digby Bell and his wife, Laura Joyce Bell; Mrs. G. H. Gilbert, Harry Woodruff, who built the island's first upside-down house, Aloha, on Morey Lane; Robert Hilliard; Charles Penrose, star of the classic horror film Dark Eyes of London in 1939; William H. Thompson and his wife, Isabel Irving, who built The Captain's Cabin on Baxter Road; and DeWolf Hopper, famous for his "Casey at the Bat" narration, acclaimed acting and singing career, and for having six wives, including wife number five, Hedda Hopper.
After World War I, in 1918, the automobile came to Nantucket, changing the old way of life. In the 1920s, many families from the Actors Colony moved to Hollywood, where the burgeoning "talkies" industry offered year-round work.
In 1920, a movie set was built on the Casino grounds and several summer 'Sconseters, including Miss Agnes Everett (who started the Chanticleer in 1901), were cast in the silent film that was called Sinners.
Writer Robert Benchley was a favorite for his wit and performances in his own 1923 skits "If Men Played Cards as Women Do" and "The Treasurer's Report," among his and the Benchley family's many other contributions to the 'Sconset scene. Tony Sarg took the stage as an able comedian, and drew impromptu, humorous sketches of people at the Casino. Distinguished actress Patricia Collinge was devoted to the Casino reviews. Well known for her film role in The Little Foxes, written by Lillian Hellman and starring Bette Davis, Collinge was present at the summer 1942 showing at the Casino, and thrilled the audience with her grace and charm after the film. A year later she portrayed Joseph Cotton's cloying sister in Alfred Hitchcock's classic film Shadow of a Doubt.