This chapter addresses the early stage adaptations of several of Baum’s books. The first musical comedy in 1902–1903 generated huge excitement, and inspired Baum to continue with his second novel in 1904. The following two decades were full of interchange between novels, stage productions, and films, with each iteration fueling interest in the world of Oz and its fantastic characters. The chapter examines several of these productions, including basic information about their contributions, but the focus is on the relationship between the stars chosen for the roles and the talents (dancing, singing, comedy, drama) they brought to the version they starred in. For example, Montgomery and Stone, a comedy duo popular in vaudeville and on Broadway, were the stars of the first show. Thus, it was the Tin Woodman and the Scarecrow who were the focus. Other performers, such as Charles Ruggles and Charlotte Greenwood, were the main attractions to their specific productions, too. In the end, the most successful Oz productions found clever ways to allow star players to shine and showcase their talents while maintaining some element of the narrative. It is this formula that would, in part, lead directly to the powerful impact of the 1939 film musical.