Ann Montgomery Woodson, a local African-American icon, started the business of Little Harlem as an ice cream parlor in 1910. It was a billiard parlor in 1922, and a supper club in 1929, before establishing it as a cabaret in 1934. The Little Harlem was a freewheeling joint that welcomed black and white, straight and gay, gambler and call girl.
Woodson was born in Americus, Georgia. When she was an infant, her parents moved to Los Angeles, California. She attended school in Los Angeles as well as in Texas before moving to Buffalo, New York, in 1910. Shortly after her arrival in Buffalo, Ann opened an ice cream parlor at 496 Michigan Avenue, which would later become the location of the Little Harlem.
Years later, the ice cream parlor was converted into the Little Harlem Hotel and nightclub. Woodson began the cabaret that initiated the nightclub in 1934. In the early days, the Little Harlem became a major showcase for aspiring new stars during an era when it was difficult for them to obtain jobs in their professions elsewhere. The roster of stars included both black and white performers such as Louis Armstrong, Billie Holliday, Bing Crosby, Vincent Lopez, Cab Calloway, and Dinah Washington, among the more popular names who performed at or visited the hotel and club. The club was also frequented by celebrities such as Heavy Weight Champion, Joe Louis and Sugar Ray Robinson.
Woodson was a member of the Buffalo Chapter of the National Association for the Advancement of Colored People (NAACP) and the Michigan Avenue YMCA. Her death, on April 11, 1978, ended a career that spanned nearly seventy years. The club, which was placed on the roster of national historic sites, was destroyed by fire during the 1990s.