Gladys Bentley in White Tux

Gladys Bentley was frequently harassed for wearing men's clothing.

Gladys Bentley

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.

Sissy Man Blues

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

Alberta Hunter, who was very popular in South Side cabarets and lived in Bronzeville in the 1920s, recorded several queer-themed songs.

The Social Evil in Chicago

Vice Commission of Chicago, The Social Evil in Chicago: A Study of Existing Conditions

Map of the Levee District

Map of the Levee District. [Source: Chicago Historical Society (ICHi-37088).]

Tony Jackson's Draft Card, Part 2

Tony Jackson's draft card. [Courtesy of the National Archives and Records Administration.]

Tony Jackson's Draft Card

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.]

Pretty Baby

Tony Jackson's most famous song: "Pretty Baby"

Pekin Cafe

View of the Pekin Cafe from across the street. [Courtesy of the Chicago Historical Society.]

Tony Jackson and Friend

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

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

Grand Masque Ball

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 a New Sex Problem Here?

“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"

“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…

José Sarria

José Sarria, first openly gay person to run for public office in the US. Photo by Ron Schlittler

Liz Malia and Jarrett Barrios

Liz Malia (left) State Representative; Jarrett Barrios (left) State Senator. Photo by Ron Schlittler.

1974-1975 Mr David Ad

1974 Mr and Miss David Registration

Marco Polo Hotel Ad 1974