This chapter explores a series of arts-based workshops conducted with male university students at the University of Malawi’s Chancellor College as part of an arts-based gender-transformative programme, Brother2Brother. The chapter begins by situating the programme within the specific social-cultural landscape of the college and existing college initiatives. Part I reflects on the workshops conducted with the 15 participants, analysing how arts-based techniques—rap, poetry, drawing, and image theatre—facilitated a critical examination of understandings of masculinity, gendered power dynamics and social norms. Part II examines the outreach activities implemented by these participants in 17 secondary schools across Zomba District. Using examples from two schools, I analyse how the interactive game Masculinity Game Show and the play A Man is as Big as His Penis stimulated discussion among adolescents. Ultimately, I argue that arts-based methodologies enabled the young men to interrogate hegemonic masculinities, while drama-based tools empowered adolescents to critically reflect on youth masculinities, peer pressure and sexuality.