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Bronzeville, Near South Side

Decades Before Boystown, South Side Jazz Clubs Were A Haven For Queer Chicagoans

From the 1930s through the mid-1960s, drag shows were among Bronzeville and Woodlawn’s hottest nightlife attractions, attracting patrons of all races and sexual orientations.

611 E. 63rd St.., is where the Kitty Kat Club once operated. A building remains there – the only one on its block – as seen on June 29, 2022.
Colin Boyle/Block Club Chicago
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BRONZEVILLE — Long before North Halsted Street became the epicenter of Chicago queer nightlife, a vibrant drag scene thrived on the South Side, buoyed by jazz clubs in Bronzeville and Woodlawn.

Jazzheads know the headliners’ names, even if the venues are now a memory. Clarinetist and bandleader Jimmie Noone played female impersonator shows at the Cabin Inn, 3119 S. Cottage Grove Ave., until the club was shut down because of a licensing dispute.

The Kitty Kat Club, 611 E. 63rd St., was known as a haven for gay South Siders and its on-the-pulse music programs, tapping jazz talents including pianists Ahmad Jamal, John Young and King Fleming before their ascents.

And Sun Ra and his Arkestra, icons in avant-garde jazz and Afrofuturism, backed drag shows at Queen’s Mansion, a venue which succeeded Joe’s DeLuxe, another longtime drag venue at the same address, 6323 S. King Drive.

Venues came and went, and new genres arose to occupy jazz’s pop-cultural dominance, but drag balls stuck around the South Side through all these transformations. The buildings that housed these popular shows are long gone, driven out amid cultural and economic changes.

Credit: Colin Boyle/Block Club Chicago
Homes in Woodlawn as seen from above 63rd Street on June 29, 2022.

‘They Imitated All The Stars, And They Did It Well’

Northalsted is known now for its thriving drag scene — but drag events flourished on the South Side starting in the 1930s.

The South Side’s longest-lasting and most famous drag event was Finnie’s Masquerade Ball, a racially integrated Halloween drag show founded in 1935 by Alfred Finnie, a gay, Black man-about-town. A gambler, Finnie was killed after one of his bets went south in 1943, but the ball he founded continued for nearly 50 more years in various venues.

The Jewel Box Revue — a touring impersonator troupe long emceed by Stormé DeLarverie, a lesbian and drag king later credited with inciting the Stonewall uprising — held extended residencies on the South Side from 1958 to 1966. 

Singer and drummer Earl “Teddy” Thomas, now 92 and living in South Holland, played in a trio backing the Jewel Box Revue in its short-lived but popular stint at the Roberts Show Lounge, 6620 S. King Drive.

“It was a great show — very entertaining, very well-received. Some performed as Sarah Vaughan, some as Dinah Washington. … They imitated all the stars, and they did it well,” Thomas said. “Not many clubs put on full shows. But that’s what Jewel Box Revue was.”

As for the Queen’s Mansion performances, University of Chicago sociologist William Sites said Sun Ra may have felt simpatico with the outre, unapologetic aesthetic of female impersonator shows. Sites tracked the Arkestra’s bookings in his recent book, “Sun Ra’s Chicago: Afrofuturism and the City.”

“Sun Ra’s own persona as a musical performer conveyed a different kind of identity than the, let’s say, reestablished hypermasculine, individualist identity we see from conventional 1950s jazz musicians,” Sites said. “I like to think that the clientele and sort of ambience of a club like the Queen’s Mansion probably influenced Sun Ra’s repertoire of the time, too, which was a lot of Broadway show tunes in elaborate — you might even say flamboyant — arrangements.”

Sites said he came upon evidence of more “fugitive” DIY balls that popped up around the city while researching his book, but few, if any, photos have survived.

“The late ’40s music scene and its kind of relationship to queer social life was much more varied. There were shows at established commercial clubs like Joe’s DeLuxe, but there were also special-event drag balls that would attract huge numbers of queer South Siders, most of them probably working class,” Sites said.

In 1970, late performer and clothier Jacques Cristion staged a latter-day version of these fugitive balls with his own underground ball series on the South Side. According to a 2000 interview in the Windy City Times, Cristion participated in Finnie’s balls for years but was moved to start his own when “most of the white kids were receiving the trophies and the Black kids were not.” 

The Near North Side drag scene was almost exclusively white during this period, though Black queens and musicians often headlined. The South Side drag and queen venues were more integrated and, crucially, largely ignored by law enforcement and social commentators, historians said.

“Within the social and cultural space of Chicago, the South Side was seen as a kind of red-light district. Identities were less policed there, at least for the first half of the 20th century,” Sites said.

St. Sukie de la Croix, a historian who sourced the research for his 2012 book “Chicago Whispers” from press clippings and hours of oral interviews, agreed.

“I can tell you North Side bars which closed down because they were raided. On the South Side, I can’t think of a single bar that closed down when it was raided” before 1960, de la Croix said.

Credit: Colin Boyle/Block Club Chicago
3119 S. Cottage Grove Ave., now 3119 S. Rhodes Ave., is where the Cabin Inn once stood and operated. The plot is now a parking lot, facility and basketball court, as seen on June 29, 2022.

The Chicago Defender remains the most thorough press record of South Side nightlife.

From the Cabin Inn’s revues of the late 1930s to the roving Finnie’s Ball, the paper covered female impersonator shows as part of its nightlife columns. The paper gave glowing reviews to Valda Gray’s short-lived revues at the Cabin Inn border.

“There should be no reason why Valda Gray’s shows are not considered the best on Chicago’s great South Side,” a Defender writer said in 1939.

By contrast, Tribune theater critic Seymour Raven panned a 1958 drag show in The Loop, also jabbing at “the threat of a new thing … rising in the east”: the Jewel Box Revue. He may not have known the Jewel Box Revue had already been performing in South Side venues for about a year — to popular acclaim — at the time he wrote the column.

“According to the casting news, this one will have 25 men [all female impersonators] and one girl. What will the girl do, wash the underthings?” Raven wrote.

Despite their popularity, drag performers could be arrested if they were seen cross-dressing offstage, or even in the club after their set until 1973. Finnie’s Masquerade Ball and Cristion’s underground drag shows took special care to organize their events on Halloween or New Year’s Eve, the only days Chicagoans had a built-in alibi for bucking gendered fashion conventions.

Credit: Colin Boyle/Block Club Chicago
5112-16 S. State St., is where the Club DeLisa once stood and operated. The plot is now a parking lot, vacant lot and part of a Burger King, as seen on June 29, 2022.

Though drag was never fully stamped out in Chicago, several factors complicated its reception post-World War II.

The return of male troops reinforced traditional gender norms, and the rise of McCarthyism and its culture of paranoia around homosexuality made gender-bending more taboo and illicit, historians said. To many, cross-dressing was only socially acceptable if it could be passed off as a silly diversion by bawdy entertainers. 

An anonymous lifestyle columnist put a fine point on this belief in the Defender’s November 15, 1960, issue:

“Most alarming and disgusting event of week occurred on Chicago’s southside Saturday and we repeat it here just as a warning for those parents who neglect warning youngsters about evils that threaten big change for the worse. The event was a party staged by several youngsters wherein they appeared in an all impersonations show. The young boys secured dresses belonging to their sisters and in some instances mothers, and proceeded to sing and dance a la Jewel Box Revue. Prices ranged from ten cents for the ‘orchestra seats; to five cents for the ‘last rows.’ Few parents and grownup friends attended the show and showed interest in what most certainly should not have been laughed off.”

Then, in the mid-’50s, the federal government initiated its push for “urban renewal,” which resulted in the rezoning and razing of disinvested neighborhoods in American cities. In Chicago, that meant displacing tens of thousands of low-income residents —many of them Black — and effectively closing once-thriving commercial districts on the city’s South and West sides.

By the early ’60s, most of the venues that once united the city’s greats in jazz and drag had vanished.

Years later, accompanied by a photographer for the Tribune, de la Croix visited the former sites of the venues that provided havens to queer people on the South Side. The Kitty Kat Club was a vacant plot, Joe’s DeLuxe a parking lot.

“They’re just gone. But when I visited, I tried to see if I could feel some sense of what had happened there,” de la Croix says. “I think you can.”

Credit: Colin Boyle/Block Club Chicago
611 E. 63rd St.., is where the Kitty Kat Club once operated. A building remains there – the only one on its block – as seen on June 29, 2022.

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