This dissertation studies poetry as a linguistic topos that traveled across cultural and class boundaries during the Song-Jin-Yuan transition (1050–1300). Literary scholars often examine poetry in light of leading literati’s cultural practices and political experience. Moving away from canonical authors and works, this project focuses instead on how poetry was used when the transformation of social institutions, the democratization of entertainment, the advent of print, and the urbanizing spaces afforded it new avenues of production and circulation. By tracing the movement of poetic messages in diverse cultural circuits, my inquiry offers a revisionist understanding of poetry as a malleable artifact integrated into urban life, which also reshaped contemporary political dynamics. Drawing evidence from historical miscellanies, excavated artifacts, local literary collections, and court documents, this project maps out an expanding poetry market and the emergence of professional poets who wrote for profit. Potential consumers of poetry consisted of both educated readers, whose demands revolutionized conventional writing ideals, and commoners, who purchased household ware inscribed with performed verses to create a space reminiscent of the theatergoing experience. The percolation of poetry in quotidian life brought about an unexpected political consequence. When entertainers updated their repertoire with contemporary events and urbanites drew knowledge from popular performance to engage with politics, poets straddled the elite and popular spheres to make a profit. Connected to publishers and performers, they commodified political struggles by spreading satires in various linguistic registers. Many further sold their public influence to powerful officials, making the dissemination of defamatory verses into service in demand.