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Xie An (320-385), an aristocratic super hero admired for his refusal to serve the court as well as his role in a decisive battle to save the Eastern Jin (317-420), is, throughout the East Asian cultural history, called a man who “set his mind on the Eastern Mountain.” Eastern Mountain, being Xie An’s mountain estate, becomes a literary trope for lofty disengagement, a moral ideal ubiquitously aspired. Who could imagine Xie An being mocked for not serving the court and even accused of making a pretension of being better than who he actually was? Xie’s motivation was questioned in the same collection of jokes and gossips where he was idolized. Whether he had more far-reading aims or whether Xie An was savvy enough to understand the devaluative effect of court service on an aristocratic man is not an issue we can solve. This paper takes this case as the beginning point to discuss how jokes were made in Medieval China. What were their social contexts and cultural implications? To what extent did the jokes rely on the literary and philosophical attainments of the audience in order to have a successful deliverance? What does that tell us about how classical texts, part of the aristocratic education signaling their social distinction, were used for a wide range of purposes with varying attitudes that could have been much more divergent and dynamic than the straight-faced sincerity with which we tend to regard those men of lofty aims?