In the sixth century BCE, Siddhartha Gautama—Buddha (“Awakened One”)—led a spiritual revolution that overturned the dominant religious authority in ancient India and, in turn, inspired similar revolutions worldwide. In this course, we explore the disruptive ideas and practices that gave rise to Buddhism and fueled the broader Śramaṇa (“Misfit Seeker”) countercultural movement in ancient India. From there, we trace subsequent revolutions within Buddhism, including the traditional “Three Turnings of the Wheel of Dharma,” and their assimilation into Tibetan and, now, American Buddhist contexts. Our study will touch on the lives and works of select Buddhist nonconformists, including the Mahāsiddha (“Psychonauts”) of India and Tibet, such as the Indian Master Naropa (c. 1016–1100 CE) and the 11th-century Tibetan Buddhist yogi Milarepa. We will also consider contemporary spiritual revolutionaries in the history of American Buddhism, for example, the American philosopher and psychologist William James (1842–1910) and the avant-garde poet Anne Waldman (1945–).