Get a Glimpse of Chicago’s Wild Forgotten ‘Roaring Twenties’ Gay Scene
Now gone and mostly forgotten, the city before WWII was once filled with some of the most open and outrageous LGBT culture in the world.
I was in Chicago a couple months ago to promote my most recent book, The Boys of Fairy Town: Sodomites, Female Impersonators, Third-Sexers, Pansies, Queers, and Sex Morons in Chicago's First Century, and took the “L” from Midway to Addison. From there, I walked to my B&B in Boys Town. The rainbow-striped pylons that I passed along Halsted reminded me of the many sites of gay activity that, now gone and mostly forgotten, once dotted the city, first during an early period of the gay community’s underground activity and virtual invisibility and then, during the Roaring Twenties, a period of widespread acceptance and visibility.
In the late 1850s, bordellos such as Roger Plant’s at the corner of Wells and Monroe, where a health club now stands, retained a young man or two for clients whose tastes ran more to the homo than the hetero. Another was at 140 West Monroe that, in recent years, has become home to a Starbucks. On August 8, 1888, the police arrived there and arrested two women and four men to the catcalls of the neighbors who had flocked around the paddy wagon. Two of the men answered to “Marguerite” and “Lillie,” and all four wore makeup. Other bordellos, called “boy houses,” catered strictly to gay men. Several clustered around the intersection of Randolph and Dearborn, an area known as “Bryant’s Block,” where the Goodman Center, a McDonald’s, and one of Picasso’s statues now stand, as well as along South Clark between Harrison and Polk.
Gay man could find sexual partners in out-of-the-way areas in the Loop, including the Randolph Street Bridge. The cave-like area under it, where it met the bank of the Chicago River, became a favorite, drawing young and old, wealthy and poor. Men could find willing partners in wide-open spaces, too. Those who wore a red necktie and strolled up and down the block of State Street between Randolph and Washington, would soon be solicited by another man.That short promenade was along Marshall Field department store, now Macy’s, and gave a queer twist to the notion of shopping.
There was no “gay neighborhood” per se. Most gay men lodged in the Loop, as did John M. Wing. His diary mentions that he arrived in Chicago from New York in the summer of 1865 and found a job as a reporter for the Chicago Tribune that very day. At first, Wing roomed in boarding houses, but later lived in hotels, such Brigg’s House at the northeast corner of Wells and Randolph and the Shepard Building at the southeast corner of Dearborn and Monroe. The site of the hotel now holds a bar, and the Shepard Building was, in time, replaced by a bank. Finally, he moved to a house at 743 Congress where he invited men for the rest of his life. The house was demolished to make way for what would become the Eisenhower Expressway in the early 1950s, In the meantime, other gay men began moving into a neighborhood called Towertown on the north side of the Chicago River.
Shoddy Towertown spread several blocks in all directions from the Water Tower. An inexpensive vicinity, it drew gay men and Bohemians—artsy, literary, and politically-progressive young men and women whose slogan was “free love”—to its hundreds of boarding houses.
By the onset of the Roaring Twenties, gays and straights mingled at The Dill Pickle at 18 Tooker Alley just off Dearborn, now a parking garage. Its founder sponsored lectures and debates—one, “Do Perverts Menace Society?,” drew an SRO crowd—as well as masquerade balls, often at Turner Hall at 820 N. Clark, now an apartment building, that many attended in drag. The Phalanstery, a restaurant at 915 Rush, where a women’s boutique clothing store now stands, sponsored similar debates and lectures. The Seven Arts Club, which met at different locations and also held lectures and which drew old ladies and young gay men, was best known for its drag shows. On the other hand, the clientele of Diamond Lil’s, located where the rear of the North Bridge Shops abuts Rush Street, was chiefly gay.
Other venues dotted Towertown: Green Mask Inn, Wind Blew Inn, The Derby, K-9 Club, and Erie Cabaret where Frances Carrick sang. A female impersonator, she was arrested for running two bordellos—one at 43 N. Dearborn (now a skyscraper), another at the Corner of Erie and LaSalle—and for murder.
Few of Towertown’s habitués have become famous, but one, Henry Gerber, made history in 1924. He founded the Society for Human Rights, the first legal organization in the U.S. to advocate for gay men and the first homophile magazine, Friendship and Freedom. Its five members lived within or on the outskirts of Towertown: Gerber and Henry Teacutter roomed at 1719 Crilly Court, which was designated a Chicago historical landmark in 2001; John T. Graves and Ellsworth Booher lodged at 1151 Milton, where an apartment building has been built; and Al Meininger rented at 532 N. Dearborn, where the Fort Dearborn branch of the U.S. Post Office is now located. When police arrested Meininger for consorting with a teenager, Meininger directed them to Gerber who was not only arrested but fired from the Lakeview branch of the Post Office. Evicted, he moved briefly to a boarding house near the lakefront before leaving for New York in disgust.
A group of young men met at the lakefront then meandered together along its esplanade, picking up those who sat on park benches waiting for them. Another cruising spot was Washington Square Park (aka Bughouse Square) across from the venerable Newberry Library. After the Dill Pickle and other venues closed for the night, gay men drifted there to find sexual partners and either took them home or to bathhouses nearby, including Jack’s (829 Dearborn, now an apartment building) or the Wacker Baths (674 ½ North Clark), where they could rent a cheap room for the night. Jack’s (829 Dearborn, now an apartment building) or the Wacker Baths (674 ½ North Clark, where the rear of the building that now houses the Consulate General of The People's Republic of China stands).
In the meantime, Bronzeville, a South Side neighborhood, had become a safe harbor for thousands of African Americans who had left the South in search of better lives. Its entertainment district, “The Stroll” (or South State Street), offered African-American men who made no bones about being gay employment, fans, friends, and lovers.
Standing only 5'2", Frankie “Half Pint” Jaxon recorded scores of 78s, headlined his own radio program, and produced the live shows of up-and-comers Ethel Waters and Bessie Smith. A powerhouse on and off stage, his notoriety skyrocketed during the Roaring Twenties with his outrageous performances—He sang the female’s role in songs using his trademark falsetto—that drew SRO crowds to the Sunset Café (315-17 East 35th Street, now a shop that sells beauty and hair supplies stands), the Grand Theater (1911 S. State, where an apartment building was recently raised), or any hotspot where he appeared. He re-recorded the blues standard “How Long, How Long,” which is about anticipating a train’s arrival, but changed its lyrics to a rumination on a penis. Cab Calloway heterosexualized the lyrics of Jaxon’s “Willie the Weeper” and re-recorded it as “Minnie the Moocher.”
Cabarets along East 35th or The Stroll—the Plantation Café, Club De Lisa, Sunset Café, and many other—gave the Sepia Gloria Swanson, Sepia Joan Crawford, Nancy Kelly, and scores of other drag queens good-paying jobs entertaining. Kelly (née Lorenzo Banyard) made five times as much performing weekends as he did for a week washing dishes at the YMCA (3763 S Wabash), which was listed on the U.S. Register of Historic Places in 1986.
In October 1935, a few days before Halloween, the Cabin Inn at 3119 Cottage Grove, now an empty lot surrounded by a chain-link fence, hosted a faux, very campy wedding between the “midget dancer” Shorty Burch, and Muriel Borsack. The bridal party included drag queens dressed to the nines, who inspired Alfred Finnie to sponsor drag balls Bronzeville. At first they were held in any joint Finnie could find, including in a tavern’s basement at the corner of 38th and Michigan. Attended by blacks and whites, gays and not, and famous across Chicago, the balls continued for decades after Finnie’s death.
Bronzeville also had its share of boy houses. Madam Brock, perhaps a drag queen, held séances and read fortunes at her place at 5519 Drexel, across the street from what is now the University of Chicago’s Smart Museum of Art, but its chief attraction was the sexually-available men who worked there. Treville Holmes, a postal employee like Gerber, owned a place on 50th Street that boasted Montgomery Clift, playwright Thornton Wilder, and other cultural big shots as its clients. One night in late November 1935, a dozen members of Towertown’s Seven Arts Club visited a boy house at 3549 South Park Way, now a private residence, but before they could get through the foyer, police swooped in and hauled them off to jail. But sex partners could be found along the The Stroll, too. At 31st Street, five different men solicited Ben Reitman, a physician and city health officer, in one evening, or so Reitman’s biographer revealed in The Damndest Radical. At the same spot a few weeks later, three men solicited a vice detective who arrested them.
The visibility that gay men enjoyed during the Roaring Twenties dwindled at the end of the decade and finally died out by the end of the 1930s. It would be a quarter of a century before gay men would become visible again, fighting for their rights during what would be called the Gay Liberation Movement. Keeping track of the sites of the activity of past gay generations is all well and good, but the lives of the men who were there, engaged in the activities, are more important and far more interesting, as accounts of their lives, such as those in The Boys of Fairy Town, confirm.
Jim Elledge is the author of the recent book The Boys of Fairy Town: Sodomites, Female Impersonators, Third-Sexers, Pansies, Queers, and Sex Morons in Chicago’s First Century published by Chicago Review Press.