How Gay Culture Blossomed During the Roaring Twenties

On a Friday night in February 1926, a crowd of some 1,500 packed the Renaissance Casino in New York City’s Harlem neighborhood for the 58th masquerade and civil ball of Hamilton Lodge.

Nearly half of those attending the event, reported the New York Age, appeared to be “men of the class generally known as ‘fairies,’ and many Bohemians from the Greenwich Village section who...in their gorgeous evening gowns, wigs and powdered faces were hard to distinguish from many of the women.”

The tradition of masquerade and civil balls, more commonly known as drag balls, had begun back in 1869 within Hamilton Lodge, a black fraternal organization in Harlem. By the mid-1920s, at the height of the Prohibition era, they were attracting as many as 7,000 people of various races and social classes—gay, lesbian, bisexual, transgender and straight alike.

Stonewall (1969) is often considered the beginning of forward progress in the gay rights movement. But more than 50 years earlier, Harlem’s famous drag balls were part of a flourishing, highly visible LGBTQ nightlife and culture that would be integrated into mainstream American life in a way that became unthinkable in later decades.

“In the late 19th century, there was an increasingly visible presence of gender-non-conforming men who were engaged in sexual relationships with other men in major American cities,” says Chad Heap, a professor of American Studies at George Washington University and the author of Slumming: Sexual and Racial Encounters in American Nightlife, 1885-1940.