The emergence of a vibrant literary, culture and arts scene promotes Singapore's claims as a hub for arts and culture in the Asian region, and as a global arts city by the 21st century. The richness and variety of Singapore literature from the early post-colonial years are evident in the evolution of a Singapore literary culture. The diaspora of Singapore writers and their facility with English as a global language simultaneously allows them to contribute to world literature and to internationalization of Singapore's literary heritage as transnational writers. Despite this, there seems to be a disconnection between literature education in schools and the broader literary and arts culture of Singapore. This paper explores the state of the subject Literature in secondary schools in the context of this progressive, vibrant and diverse Singapore environment.