As global attention to mental health issues continue to increase day by day, its media and theater portrayals become increasingly imperative. This chapter contributes to the body of knowledge on mental health and how it presents masculinity as a construct that must be redefined rather than resisted in Nigeria. Both media and theater serve as functional vehicles and tools for social engagement, dialogue, and change. However, most studies on mental health issues in Nigeria have focused on gender-based violence, emotional stress, and trauma as they affect women. There are few studies that address mental health issues and how they affect men in the Nigerian context. Consequently, this chapter explores the salient, yet silent struggles of men and how they endure societal expectations particularly the emotional burdens that often go unspoken. Through media and textual analysis as methodological choice, the chapter asserts that media and theater can be a vital platform for advocacy, offering a safe space for dialogue and healing among men. The chapter further advances the imperativeness of mental advocacy, gender studies, and the integration of mental health themes into the media and theater curricula by fostering collaborations between both practitioners and mental health professionals to enhance awareness and support.