This dissertation is a study of cynical practices against a backdrop of increasing censorship and surveillance in Chinese everyday life. It takes a particular view that with its distinctive Chinese shades and hues, cynicism (in this work “wanshi”) as a mode of behavior and an outlook on life is embedded within what is often considered a marginal culture called “rivers and lakes” (jianghu). Oscillating back and forth between utopian vision and political reality, the cynics’ odyssey through space and time began in the imaginary world of jianghu conceived by fourth-century B.C. Taoist philosopher Zhuangzi. The jianghu of his literary creation is allegorically set in nature, a space outside officialdom and social order; only in this world can one truly roam free, unencumbered by constrictive career ambitions and complex human relationships. Jianghu alluded to the lifeworld of a hermit. About six centuries later, Zhuangzi’s vision captured the imagination of the wider intelligentsia in an empire crumbling under social and political turmoil not unlike that of the philosopher. Jianghu became a cultivated fantasy space among the literary and political elite in the cultural milieu characterized as “aesthetic hermitism”: from the construction of pleasure gardens, to hosting literary salons and drinking parties, to patronizing a hermit to dwell in the private garden for the otherworldly aura and the worldly status it brought to the hosts. Hermits jumped aboard the zeitgeist, moving from mountains and caves initially, to private gardens and later to court and marketplace that were emblematic of power and materialism. By this time, hermitism was no longer defined by the dwelling place, but rather by the inner strength unperturbed by earthly matters and surroundings. Eventually in the Song dynasty (960 – 1219), jianghu evolved into a socialized milieu for not just various misfits and outcasts that had been forced out of the longstanding clan system, but also powerful figures hiding in the imperial court with treacherous ambitions. Of the myriad jianghu figures, storytellers who disseminated historical tales of fraternal love and loyalty in taverns, in the name of righteousness, were key to popularizing the hitherto elite culture. These deviations from the original jianghu of Zhuangzi’s conception shaped the (a)social character of the emerging cynic, who is at once a realist and a player. This circuitous route to the genealogical line of the cynic affords the facilities and perspectives necessary to examine the contemporary figure of jianghu. Drawing on two years of ethnographic fieldwork in several artist communities in Beijing, particularly Songzhuang, where the artists referred to themselves and their social milieu as intrinsically jianghu, much of this dissertation looks into their lifeworld – conditions of their “habitat”, mode of existence and worldview – and their everyday practices and skills pertaining to agency and communication in order to bypass surveillance, censorship and outright subjugation. Bearing some resemblance to the bygone raconteurs in taverns, the artists’ techniques of coded communication were quickly appropriated and innovated by the general public on the constantly monitored social media and everywhere in cyperspace. Rather than discuss jianghu as a separate entity from the mainstream society, this work proposes to view it from a “practice” perspective. As such, the last part of the dissertation restages two larger-than-life online battles to reflect upon a range of potentialities of cynical practices as opposed to direct confrontations and ironic expressions in the age of hyperconnectivity.