This article examines the life and poetry of Wang Wei, one of the most distinguished courtesan poets of the Ming dynasty. Through an examination of her courtesan career, her friendship networks in literati circles, and her adoption of multiple identities such as xianren (person of leisure), daoren (person of the Dao), and shiren (poet), it seeks to illustrate what I believe is an important explanation for the flourishing of late Ming courtesan and literati culture. The rising prominence of learned and literary courtesans was strongly connected to a new social formation of nonconformist literati, the “men of the mountains” (shanren). These nonofficial urban elites of the prosperous Jiangnan region fashioned themselves as retired literati, devoting themselves to art, recreation, and self-invention, instead of government service. In constructing an “artistic and hedonistic counterculture,” they encouraged the involvement of both courtesans and literary women of the gentry class.