University of Chicago Sociology Professor Ernest Burgess encouraged his students to analyze the experiences of African American homosexuals on the South Side throughout the 1930s. [Courtesy of the University of Chicago - Regenstein Library]
Blues Singer Lucille Bogan
Blues Singer Bessie Smith
Blues Singer Ma Rainey
In 1928, Gertrude ‘Ma’ Rainey, a South Side resident, stated in a song she wrote - entitled “Prove it on Me Blues" - that “she [wore] a collar an tie,” and “talk[ed] to the gals just like any old man.”
Gladys Bentley was frequently harassed for wearing men's clothing.
Often dressed in men's clothes, Gladys Bentley played the piano and sang her own raunchy lyrics to popular tunes, while flirting with women in the audience.
In “Sissy Man Blues,” a traditional tune recorded by numerous male blues singers, the singer demanded, “If you can’t bring a woman, bring me a sissy man.”
Alberta Hunter, who was very popular in South Side cabarets and lived in Bronzeville in the 1920s, recorded several queer-themed songs.
Vice Commission of Chicago, The Social Evil in Chicago: A Study of Existing Conditions
Map of the Levee District. [Source: Chicago Historical Society (ICHi-37088).]
Tony Jackson's draft card. [Courtesy of the National Archives and Records Administration.]
Tony Jackson's draft card shows his birth date and his employer of the time "The Pekins Theater." [Courtesy of the National Archives and Records Administration.]
Tony Jackson's most famous song: "Pretty Baby"
View of the Pekin Cafe from across the street. [Courtesy of the Chicago Historical Society.]
Tony Jackson and Friend (Probably Glover Compton), The Historic New Orleans Collection, Williams Research Center 92-48-LMSS 509, F. 48, New Orleans, LA. Courtesy of The Historic New Orleans Collection, Williams Research Center
Tony Jackson at Piano, The Historic New Orleans Collection, Williams Research Center, 92-48-LMSS 508, F. 53, New Orleans, LA. Courtesy of The Historic New Orleans Collection, Williams Research Center
As early as 1912, The Chicago Defender encouraged its readers to attend Drag Balls. At this "Grand Masque Ball," the third prize - a leather purse - was given to the best female impersonator.
“Have We Had A Sex Problem Here?”, Chicago Whip, November 27, 1920: Sherman Robinson, 3521 Wabash Ave, was the complainant in one of the most peculiar divorce cases to yet be heard in Chicago, when last week he asked complete divorce from his wife,…
“Nosey Sees All Knows All,” Chicago Whip, November 6, 1920, 2: "Nosey was out on Haloween Eve and what he saw would fill a book. He saw one lady, the mother of six children, out in men's clothes, switching like a bride's train with a…