This chapter focuses on the discourses of nationalism in literature in Singapore and Malaysia. It explores the consequences of nationalism on literary representations of Singapore and Malaysia. It examines the depiction of nationalism in Edwin Thumboo's Ulysses by the Merlion, Alfian bin Sa'at's The Merlion, and Karim Raslan's Heroes. The findings suggest that in both Singapore and Malaysia, state-sponsored discourses of nationalism, which mark entry into nationhood after colonialism in both cases, are built on ambivalence.