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This article explores how one of the most typically hyper-masculine cultural arenas in Britain and America has evolved over the past 30 years, as rap artists decide to reject the stoicism of toxic masculinity in favour of promoting healthier conversations surrounding men’s mental health and associated coping mechanisms. Though rap has always been vocal about mental distress, its dominant narratives have evolved over the past 30 years to talk more specifically and positively about mental health issues. Over time rap has begun promoting therapy, medication, self-care and treatment, rather than self-medication via drugs and alcohol, or violence against the self or others. This is symbiotically informing and being informed by society’s changing ideas about masculinity and the construct of gender. In order to explore the evolution in discussions around men’s mental health from the 1990s to the present day, this article is split into three sections, each focusing on a different decade. I closely analyse the lyrics of one rap song in each chapter, which has been selected to represent rap’s general trends regarding discussions of mental health from that decade. I also briefly explore other songs that prove the decade’s trends. This article draws upon academic research as well as personal interviews undertaken with Solomon OB (2016’s National Poetry Slam champion), and Elias Williams, founder of MANDEM.com (an online media platform engaging with social issues and shining a light on young men of colour). I posit that rap culture is often wrongly overlooked as a forum for progressive social change, explaining why it is crucial that academia further appreciates and examines rap’s potential for changing cultural perceptions of masculinity and mental health.