This chapter discusses the theme of mental health in selected works of Anglophone fiction from Brunei Darussalam and Malaysia. The Mental Health Act was formed in Brunei Darussalam in 2014 and passed in Malaysia’s Parliament in 2001 with the latter’s implementation in 2010. Given the growth of mental health awareness in recent years, it is timely to examine the way that literary works have contributed to conversations about challenging social taboos around mental health to acknowledge it as an integral aspect of overall health. Within Southeast Asia, a culture of silence around mental health disorders and illnesses has been prevalent due to various views such as perceived ideas of weakness, associated shame, and a negative cultural perspective that a mental health condition signifies an inherent vulnerability. In the Malay-Muslim dominant nations of Brunei Darussalam and Malaysia, a literary discourse about mental health struggles is emerging in contemporary Anglophone works. In this study, Kathrina Mohd Daud’s The Witch Doctor’s Daughter (2022) and Hanna Alkaf’s novels entitled The Weight of Our Sky (2019) are examined to elicit a comparative analysis of their portrayals of a host of mental health issues, including hysteria, anxiety, and obsessive–compulsive disorders. Johansen’s semiotic definition of literary discourse (2007) is brought to bear on reading the (re)presentations of mental health issues in these fictional works that invite readers to be inquisitive about and contemplate on a multifaceted, rather than unidimensional, understanding of mental health challenges to identity formation, with their onset occurring during childhood, adolescence and young adult years in these novels. Furthermore, these literary works foreground contextual factors of local and national spaces to understand external environmental influences that inform and shape the manifestations, management, and medication of mental health challenges in these nations.