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This chapter traces the rise of Louis Armstrong to stardom during the 1920s, and the emergence of jazz as the defining music of the decade—a period now often called the “Jazz Age.” Armstrong’s historic recordings, the “Hot Fives” and “Hot Sevens,” are assessed, as well as his work with influential pianist Earl Hines. These developments are placed in the context of the growing importance of Chicago in the jazz world of this era, and the stylistic changes brought about by this geographical shift. The chapter also looks at the leading exponents of Chicago jazz, especially cornetist Bix Beiderbecke and saxophonist Frankie Trumbauer, as well as the work of Paul Whiteman, Pee Wee Russell, Sidney Bechet, and Jack Teagarden.

In the fall of 1927, Rollini was in a position to set up a top band and he selected an all-star team. From Jean Goldkette's band he had a.o. Bix Beiderbecke, Frank Trumbauer, and Don Murray. Others include Sylvester Ahola, Frank Signorelli, and Bobby Davis. He called his band the New Yorkers after the Club where they worked. Their music was quite advanced and not suited for the general public.Publicity was good, colleagues came to listen, but the public stayed away, so it ended after a few weeks. During those weeks several recordings were made under various names, including Rollini's and Trumbauer's and Red Nichols'. When it ended, his band members went their various ways and Rollini accepted an offer to go abroad.

This chapter considers Louis Armstrong's association with Lil Hardin's band, after his split from Fletcher Henderson's band. His next four years in Chicago were to be spent composing a body of work in the form of the Hot Five and Hot Seven recordings. Armstrong then followed a traditional New Orleans formula, and this “New Orleans groove” was the kind of hot jazz that was in Armstrong's blood. It differentiated him from the likes of Paul Whiteman and symphonic jazz. His collaboration with Lil Hardin helped Armstrong to make this brand of hot jazz what it was. The chapter also mentions Armstrong's attendance of a performance of Bix Beiderbecke and Paul Whiteman at the Chicago Theater in July 2, 1928. It also notes Whiteman's hiring of Bing Crosby, and how Whiteman's association with Beiderbecke and Crosby brought the worlds of Paul Whiteman and Louis Armstrong closer together than ever before.

The band-within-a-band concept caught on and Kirkeby created more of this for more record labels. The Vagabonds, the Little Ramblers, Kentucky Blowers, Five Birmingham Babies, and the Goofus Five. The latter was named after the "goofus" a novelty instrument that was used by Rollini in addition to his bass saxophone to produce great jazz. In 1925 trumpeter Red Nichols and trombone player Tommy Dorsey were hired, which brought the band to an artistic top. Even Bix Beiderbecke stayed with the band for a few days, as Red Nichols' guest, but didn't join. For Kirkeby, this trend meant a financial loss.