Initially, Gay Street wasn't a public thoroughfare, just an alley entrance to the stables behind some charming Federal houses built in 1827 on Christopher Street by Village manufacturer Samuel Whittemore, to provide housing for the area's middle classes. Its 1827 houses faced the stables, their early residents being blacks in service to wealthy families of Washington Square North. Even after the last of its stables were replaced in the 1840's by the present row houses there, the alley retained the scent of undesirability. The rich left the square and Gay Street became an impoverished and dangerous ghetto that lasted longer than its counterparts in the South Village.
After shedding its ghetto status in the 1920's, Gay Street gained national recognition as the mythical touchstone of Greenwich Village. It happened because two sisters from Ohio rented the basement of 14 Gay Street and lived there while they sought fame and fortune in New York. The younger one hoped to become an actress while her older sister wrote stories in their apartment and submitted them to publishers. Ruth McKenney's "My Sister Eileen" tales became a fixture of the prestigous New Yorker magazine and were published as a book in 1938. They forever fixed an impression of life in Greenwich Village as an impromptu whirl among loony but likable oddballs.
McKenney's deft humor stirred the mix into a myth of great durability. My Sister Eileen became a Broadway comedy starring Shirley Booth, which opened the day after Christmas 1940 and ran 2 years. Rosalind Russell played Ruth in the film version, and again a decade later in a Broadway musical version, "Wonderful Town", with a score by former Villagers Betty Comden, Adolph Green, and Leonard Bernstein. CBS televised "Wonderful Town" in 1958, with Russell and several others from the original cast, while Hollywood made a second film of the tale in 1955.
Tragically, Eileen never knew the full extent of her legend. Four days before her comic adventures first appeared on Broadway, she was killed in an auto accident in California that also claimed the life of her new husband, novelist Nathanael West.