This article assesses the interconnected nature of Southeast Asia around 1900, the transnational entertainment scene in Southeast Asia, and the role of Singapore as a hub for commerce, shipping, and entertainment. The global and regional development of transportation and communications technology and networks facilitated the movement of people, goods, ideas, and amusement forms. The article is based primarily on archival research from colonial newspapers in the region. It surveys and maps more than one hundred itinerant entertainment companies that travelled throughout Southeast Asia around the turn of the century, thereby creating and visualising a circuit of entertainment.