When one thinks of countries that exercise press controls and censorship, one does not necessarily think of Japan or Singapore especially when countries like China are renown for their draconian press censorship laws. In the past few years, the spotlight as gently shifted to Japan and Singapore as both countries have made headlines for issues between the press and the government. Although total press censorship is not implemented in either country, it is rather the manner in which the relationship between the press and the government has been evolving with especially with recent changes in both countries governments. Through an analysis of Japan and Singapore amongst the backdrop of the theories of the press, I will argue that neither country perfectly fits into a single model, but rather is a combination of various models. Through case studies on press coverage of the Asian Financial Crisis, and the Umbrella Revolution, I will explore how the various voices of the media and how one can see different levels of the voice of the government in different news outlets. As a whole I analyze the relationship between the government and the media in Singapore and Japan in this current day and how they came to be through looking at their media systems as a whole, applying theories of the press to each country, and case studies on newspaper coverage of events relevant to the region.