This chapter examines the 1920s as an era, specifically as the Prohibition era, and looks at how certain aspects of the decade famously came to define the character of the city of Chicago. After all, Chicago, literally the world’s capital of saloon culture, was where the battle of the wets and the drys was most conspicuously fought during the thirteen years till Repeal. Democracy trains people to choose their lives, for good or ill, and a sumptuary law virtually forces a free people to rebel. The 1920s was a rebellion decade generally. Moreover, there was jazz, the greatest portmanteau concept in the history of the American language. “Jazz” meant everything that was new, dangerous, delicious, and liberating. Jazz was the opposite of the ice-cream social and the sermon. Yes, it was music, but, even more, it appeared to be anything community leaders warned would bring down society.