The mode of embracing Islam by the Javanese has been often regarded as one of less straightforward in comparison to the one by the Malay. This is clearly the case with the way the Javanese perceive how they accepted Islam in the earliest stage. It can be exemplified by the two contrasting episodes in the Babad Tanah Jawi and the Malay Annals, both concerning the response of the rulers of Java and Malay as they confronted Islam for the first time. In the Babad Tanah Jawi the king of Majapahit permitted the propagation of Islam on account of his relatives’ persuasion, but he himself refused to accept it. The story implies the Javanese rulers’ initial reluctance to the new religion and essentially Javanese initiative in the process of Islamization of Java. Whereas, the Malay Annals tells a story that involves the appearance of the prophet Muhammad in the dream of the ruler of Melaka, his miraculous circumcision, and his subsequent conversion to Islam by the initiation of a foreign Muslim. The story signifies the complete ignorance of Islam on the part of Malay ruler and the overwhelming nature of his conversion. An overall difference is that while in the Javanese narrative Islam was not accepted in Java without question, the supremacy of Islam over the local community is apparent in the Malay narrative. This paper will attempt to contextualize the two literary narratives and explore their further implications.