Walter Winston was born in Atlanta, Georgia. His family, like many other African Americans, moved north to Chicago for a better life. In the 1920s Winston took the name of a Hollywood Star and as Gloria Swanson won several prizes in Chicago’s drag balls.
In 1928 the Sepia Gloria Swanson (as she was billed) was hostess at the Book Store in the city’s Bronzeville, a speakeasy with a mainly black clientele which became popular as it was known that she was a permanent fixture. Her theme song was fats Waller’s “Squeeze Me”, which she rewrote to make it raunchier. She was also known for her version of Sophie Tucker’s “Some of these days”. She moved to the nearby Pleasure Inn on East 31 St, and white thrill seekers also started to come. She then opened her own club on East 35th St. She literally entertained all night: the audience was so enthralled that the sun was up when they left. As such she was a major figure in the new Pansy Craze. Noted in her audiences were the composer William C Handy and boxer Jack Johnson.

She was a creature of the night, breakfasting in the evening and dining at dawn. She wore mainly evening gowns, was rarely in street clothing, and almost never in male attire. She was plump, jolly and bawdy, and also a good cook. She was completely accepted by the underworld and bohemian types who came to her club. Apart from those in the know, many of her clients never suspected that she was not a woman.
This lasted until Fiorello La Guardia became mayor of New York in 1934 and as part of his reforms had the police stamp out the pansy subculture. One-by-one they picked off the queer nightclubs. The Ubangi, almost the last to survive, closed in April 1937.
Swanson returned briefly to Chicago in 1934, and then performed in Baltimore and Philadelphia 1935-6, and then returned to Harlem as a headline act. However she was forced into male attire offstage, and as such, Gloria's admirers failed to recognize her.
She also became ill, and had to withdraw from public life altogether. After several hospitalizations for heart conditions starting in 1936, the Sepia Gloria Swanson died in 1940 at age 33. Over 200 attended the funeral.
- “ ‘Gloria Swanson’ Buried in Harlem: Entertainer Won Fame as a Female Impersonator”. Chicago Defender, May 3, 1940.
- George Chauncey. Gay New York: Gender, Urban Culture, and the Making of the Gay Male World, 1890-1940. Basic Books 1994: 251.
- Richard Bruce Nugent edited by Thomas Wirth. Gay Rebel of the Harlem Renaissance: Selections from the Work of Richard Bruce Nugen. Duke University Press. 2002: 221-2.
- Chad Heap. Slumming: Sexual and Racial Encounters in American Nightlife, 1885-1940. The University of Chicago Press, 2009: 91-4, 233, 245, 256, 266-7, 270, 324-5n70.
- David Freeland. Automats, Taxi dances, and Vaudeville: Excavating Manhattan’s Lost Places of Leisure. New York University Press, 2009: 160.
- St Sukie de la Croix. Chicago Whispers: A History of LGBT Chicago before Stonewall. The University of Wisconsin Press, 2012: 143-5.
- Jim Elledge. The Boys of Fairy Town: Sodomites, Female Impersonators, Third Sexers, Pansies, Queers, and Sex Morons in Chicago’s First Century, Chicago Review Press, 2018: 143-4, 155.
- James F Wilson. Bulldaggers, Pansies, and Chocolate Babies: Performance, Race and Sexuality in the Harlem Renaissance. University of Michigan Press, 2010: 194-5.
Queer Music Heritage.
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