The Jazz Age, the Windy City and new female freedoms—all resulting in the 1924 murder trials of two women. Those events became a century-long metaphor for urban life in its ubiquitous, immodest greed and glitz, expressed in Chicago, a 1924 satirical play, a 1975 Broadway musical and three movies. Each one presented Roxie Hart and Velma Kelly as fictional counterparts for the two women’s momentary fame, each era expressing its unique cultural tone. We will first discuss the true history, the initial play and the later musical. With that context, we will watch the 1927 silent drama Chicago and the 1942 comedy Roxie Hart, starring Ginger Rogers. Finally, we will watch the 2002 film Chicago, a multi-Oscar winner (Best Picture, etc.), better understanding its extraordinarily complex filmmaking.