The Roaring Twenties have often been portrayed as a time of wealth, glamor, and social change. Technological advances, including more widespread electrification and increased use of automobiles, plus the growth of mass media such as radio and movies, drove a booming economy—though then as now the benefits were inequitably distributed. Inspired by movie stars and current events—notably the passage of the 19th Amendment, which gave women the right to vote—young people adopted new forms of dress that implicitly questioned traditional gender norms, and many women adopted a “flapper” style, with bobbed hair and knee-high skirts. Cabarets and dance halls became spaces for both musical and social experimentation, and the new genre of “jazz”—also known as “hot music”—was at the center of it all. 

In the 1920s, Chicago became a hub for jazz performance and recording. Much of the early development of jazz happened in New Orleans in the 1900s, where musicians transformed a broad repertoire of popular music by incorporating increasingly free, syncopated rhythms and melodic improvisation, playing off existing genres such as ragtime and the blues. Many of these musicians began moving to Chicago as part of the Great Migration—by the 1920s, Chicago’s Black population had already doubled. Popular dance bands allowed musicians to further consolidate the genre, and Louis Armstrong’s legendary cornet and trumpet solos during his 1920s Chicago residency provided a prominent source of inspiration for a new era of jazz innovation.

Some social elements of nightlife connected with 1920s jazz performance remain surprisingly familiar a full century later, among them all-night dance parties and early versions of mirrored disco balls. The scene also became a space where people navigated more fluid gender and sexual identities, complex race relations, and new laws prohibiting alcohol consumption. 

Though Chicago was heavily segregated, white audiences had been drawn to jazz since its inception, which fostered a narrative that often obscured the music’s African American origins as it became commercially lucrative. Black and white audiences shared the dance floor at “black-and-tan” (unsegregated) nightclubs, including the Dreamland Cafe, the Sunset Cafe, and the Plantation Cafe, but white musicians also appropriated and adapted the new style for whites-only clubs.

In fact, so many white musicians were interested in hearing Louis Armstrong and fellow cornetist and bandleader Joe “King” Oliver at Lincoln Gardens in 1922 that the dance hall, which normally catered to a Black audience, added a Wednesday whites-only midnight set (according to a source quoted by Armstrong biographer James Lincoln Collier). Historian William Howland Kenney says “Chicago jazz lore” holds that King Oliver took to cutting the titles off his bands’ charts to prevent visiting musicians from learning the names of the songs he played.

“Sweet Lovin’ Man” by King Oliver’s Creole Jazz Band, released on shellac 78 in 1923, features Johnny Dodds on clarinet, Baby Dodds on drums, and Louis Armstrong on cornet.

In addition to complex racial dynamics among musicians, dancers, and fans, newly permissive attitudes toward dating and sexuality flourished at the cabarets and speakeasies that booked early jazz groups. In his memoir, Chicago Uncensored, Irle Waller writes of going to all-night black-and-tan cabarets on the south side, where “many of the dancers could be seen fornicating while standing up, swaying slowly to the music.” Nightclubs on the south side also provided spaces where Black and white LGBTQ+ patrons could congregate. In her 1981 biography of Chicago-based blues singer Ma Rainey, Sandra Lieb writes that “drag shows—evenings set aside for homosexuals, lesbians, and transvestites—were common in many Harlem and Chicago nightclubs.” 

Songs with LGBTQ+ themes were “not unusual in the blues and in live black entertainment,” says Lieb—among them “Bull Dyker’s Dream,” a broadly circulated song with unknown authorship, and Rainey’s “Prove It on Me Blues,” which Lieb characterizes as “a powerful statement of lesbian defiance and self-worth” that may have reflected Rainey’s own bisexuality. Rainey sings about her “gal” leaving her, about wearing “a collar and a tie,” and about how she can “talk to the gals just like any old man.” In one stage show, Rainey included her adopted son, Danny, enacting a “female impersonation,” a precursor of modern drag performance.

Ma Rainey’s “Prove It on Me Blues,” recorded in 1928

In 1921, organizations such as the Juvenile Protective Association, founded by philanthropist Louise de Koven Bowen, grew alarmed at supposedly indecent behavior in dance halls. According to Kenney’s Chicago Jazz: A Cultural History, 1904-1930, the Juvenile Protective Association met with proprietors of many of the largest halls, who agreed to speed up their music to discourage close couple dancing, and many Chicagoans began dancing at higher beats per minute.

Because the prohibition of alcohol in the U.S. had begun in January 1920, covert drinking in nightclubs provided another focus for would-be reformists. Federal agents also began targeting Chicago nightclubs for violations of Prohibition. In 1927, the U.S. Supreme Court refused to hear an appeal from venues shut down for allowing consumption of liquor from hip flasks, and the feds subsequently raided and closed 12 Chicago clubs.

Between these crackdowns, threats from reformers, and hostility from segregationists, Chicago’s nightclubs dwindled, with many performers leaving for New York. Talking pictures, radio, and early jukeboxes also contributed to the scene’s decline. The stock-market crash of 1929, which laid bare the precarity of the decade’s prosperity, brought an end to the Roaring Twenties. 

Nevertheless, jazz was by then firmly established among the roots of modern American music, and despite the ascendancy of more conservative social norms in ensuing years, many of the exciting innovations that flourished during Chicago’s Jazz Age live on.