Chapter 2 explores the mediation of perception across the border of the tropical island. It initially discusses how the accounts of European explorers in the Pacific turned islands into discrete, highly aestheticized images. It then traces the multimedial paths along which these island-images travelled from the Pacific journals into the American cultural imaginary, manifested by Hollywood’s island films in the 1920s and 1930s, which transform the (proto-cinematic) visual strategies of the journals. While the chapter discusses the ideological needs Western island-images have been made to serve, it is especially interested in how these texts and films resist the freezing of the island into a bounded image and ask readers and viewers to reflect on their own aesthetic experience of islands. Accordingly, it complicates the cinematic gaze from the water to the island in three films: White Shadows in the South Seas (1928), The Hurricane (1937), and, finally, King Kong (1933).