Kuo Pao-Kun is the most important dramatist of contemporary Singapore. He was detained in the late 1970s for political reasons. When he was released after four and a half years in 1980, Singapore was a relatively transformed nation, in terms of political stability and economic development, as compared to the turbulent post-colonial era of the 1960s. In the early 1980s, the search for Singapore identity was a key concern within the artistic and intellectual communities. In this context, this article, focusing on the analysis of four of Kuo's plays in this period, namely Ping, Little While Sailing Boat, The Coffin is Too Big for the Hole, and No Parking on Odd Days, aims to delineate the continuum of Kuo's artistic and intellectual creation and to discuss his critical approaches to the search for Singapore identity through representations in his theatre.