The 1920s were a ball in New York when LGBTQ patrons made Webster Hall their go-to club destination.
Over a century ago, the LGBTQ community flocked to Webster Hall where drag balls were the talk of the town. Here's what you need to know about the history of the "Devil's Playground."



The Secret Gay History Of Webster Hall, America's First LGBTQ Club

Over the decades, New York City has become synonymous with a lot of things: dollar pizza, romanticized subway rats holding the aforementioned pizza, and enough gay bars and clubs to justify buying a one-pound bag of body glitter. For decades, people from every corner of the LGBTQ community have flocked to the city to find their freedom at the dingy bars and ritzy nightclubs where they’d meet, dance, and occasionally get laid. Dozens–if not hundreds–of LGBTQ bars and clubs like the Stonewall Inn have peppered the city for over a century.

These lesbians dressed openly in drag in the 1920s to turn up at Webster Hall's functions.
These lesbians dressed openly in drag in the 1920s to turn up at Webster Hall’s functions.

Outside of the West Village mainstay that’s been the sight of riots, celebration and mourning at times of great tragedy, another historic gay landmark sits in the East Village–in a venue that you’d never expect: Webster Hall. That’s right. The same place that hosts your favorite bands and scary dance parties for frat boys is also the site of what may have been the country’s first source of salvation for the LGBTQ community. Although conventional wisdom (and Google) disagrees on where America’s first official gay bar was, some have pointed to the 1930s rise of Oakland’s WhiteHorse or New Orleans’ Lafitte. Webster Hall, though, precedes these institutions of gay history by a few decades.

In the 1910s and 1920s, the iconic venue played host to a number of masquerade balls that were less Romeo + Juliet and more Paris is Burning. The drag balls were so raucous that they earned Webster Hall the nickname “Devil’s Playground,” which is what we’ve now come to associate with the cubicle at our bank where we try to argue why we can’t pay overdraft fees. As one Villager once said,We’ve sold our bed. Why sleep when there’s a dance every night at Webster Hall?”

The Rocky Twins, brothers and successful drag performers from the 1920s.

After dancing with the devil for a decade with the likes of Marcel Duchamp, Joseph Stella, Man Ray, Francis Picabia, Charles Demuth, Scott Fitzgerald and more, the 1920s brought a new series of masquerades organized by gay men themselves. They’d even show up in full drag, which was nothing short of revolutionary at a time when the state of New York had just banned the appearance or discussion of gay people on public stages. The fame of these events and the crowds they attracted led to a “pansy craze” that swept through Prohibition-era New York. That such a risqué and revolutionary act occurred over a century ago is an inspiring reminder of what these kinds of bars and clubs bring to a community that has overcome so much. In the long gay history of equality, it’s important to remember the work that Webster Hall did in normalizing and embracing the LGBTQ community.

Stay tuned to Milk for more LGBTQ history. 

Images via Harvard University, Queerty

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