The digital is now an integral part of everyday cultural practices globally. This ubiquity makes studying digital culture both more complex and divergent. Much of the literature on digital culture argues that it is increasingly informed by playful and ludified characteristics. In this phenomenon, there has been a rise of innovative and playful methods to explore identity politics and place-making in an age of datafication. At the core of the interdisciplinary debates underpinning the understanding of digital culture is the ways in which STEM (Science, Technology, Engineering and Mathematics) and HASS (Humanities, Arts and Social Science) approaches have played out in, and through, algorithms and datafication (e.g., the rise of small data [ethnography] to counteract big data). As digital culture becomes all-encompassing, data and its politics become central. To understand digital culture requires us to acknowledge that datafication and algorithmic cultures are now commonplace—that is, where data penetrate, invade, and analyze our daily lives, causing anxiety and seen as potentially inaccurate statistical captures. Alongside the use of big data, the quantified self (QS) movement is amplifying the need to think more about how our data stories are being told and who is doing the telling. Tensions and paradoxes ensure—power and powerless; tactic and strategic; identity and anonymity; statistics and practices; and big data and little data. The ubiquity of digital culture is explored through the lens of play and playful resistance. In the face of algorithms and datafication, the contestation around playing with data takes on important features. In sum, play becomes a series of methods or modes of critique for agency and autonomy. Playfully acting against data as a form of resistance is a key method used by artists, designers, and creative practitioners working in the digital realm, and they are not easily defined.