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This article examines a group of Song-dynasty biji 筆記 (miscellaneous jottings) anecdotes featuring the Northern Song literary giant Su Shi 蘇軾 (style name Dongpo 東坡, 1037–1101) playfully engaging with Buddhist encounter dialogues. These religious accounts are well known for their riddle-like language and the baffling effect they create among their readers, prompting the question of whether they were read for humor. Previous scholarship on encounter dialogues focuses on the religious perspective, demonstrating that their perplexing language and rheto- ric serve pedagogical and monastic functions. By contrast, this article explores Chan Buddhist humor from the perspective of the literati and vernacular culture by examining how encounter dialogues were incorporated in Song-dynasty vernacu- lar plays and literati storytelling. Focusing on stories that depict Su Shi’s playful engagement with encounter dialogues as a case study, this article reveals that an important part of Su Shi’s humorous image is inspired and shaped by Buddhism. It also shows that humor in these biji stories is contingent on the readers’ knowledge of Chan literature such as “recorded dialogues” (yulu 語錄) and “transmission records” (denglu 燈錄), which were popular among literati during the Song. The anecdotal materials preserved in biji suggests a mutual influence between Chan literature and vernacular entertainment during the Song. I argue that, in addition to religious functions, literary factors of performance and aesthetics played sig- nificant roles in conditioning the entertaining effect of encounter dialogues, par- ticularly when they were received outside of monastic circles.