Tsangnyön Heruka (1452–1507), the “Madman of Tsang,” was one of Tibet’s most extraordinary yogins—renowned for his radical lifestyle, uncompromising devotion to practice, and enduring literary legacy. Trained as a monk but later abandoning conventional norms, he wandered as a tantric ascetic, deliberately adopting the wild appearance and conduct of the Indian siddhas to embody a path beyond social and religious constraint. A devoted follower of the Kagyü tradition and the legacy of Milarepa, he meditated in remote sacred sites such as Tsari, Labchi, and Kailāsa, where he sang spontaneous songs of realisation (mgur) expressing profound insight into the nature of mind. Despite his outwardly provocative behaviour, Tsangnyön was deeply learned, defending his conduct through scriptural authority and tantric philosophy. He is best remembered as the compiler and publisher of the Life and Songs of Milarepa, works that became foundational to Tibetan literature, as well as a pioneering figure in the use of printing to disseminate Buddhist texts. A paradoxical figure—at once wandering yogin, influential teacher, miracle-working siddha, and cultural force—his life continues to inspire as a powerful expression of realised practice lived beyond convention.