“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.
“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.’
“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.” (Edgar, Block Club Chicago, 6/30/22)
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, Hannah Edgar, Block Club Chicago, 6/30/22