This dissertation explores the aesthetic, affective, and political dimensions of “silliness” across popular digital culture, taking the silly to be a key category of analysis for queer and trans of color studies of media. While the silly comes up widely across media, culture, and theory, its uses are surprisingly inconsistent. In this dissertation, the silly reveals itself to be aesthetically ambiguous, affectively opaque, and politically ambivalent—a deeply slippery, sticky, and messy term called on to do a range of work without being articulated as its own concept. Seizing on its internal incoherences, I argue that the silly finds distinctly transqueer/ed expressions in media through its playful de/re-familiarizations, minor aesthetic irritations, and often-unbearable affective forms. Through a series of cases, I look at how we can see, hear, and feel the silly in digital media objects. Working to upend familiar and sober ways of knowing, thinking about, and doing things with silliness across assemblages of race, gender, and sexuality, this dissertation takes the silly’s transqueer inflections to be key to studies of media and culture in the humanities that aim to resist, refuse, and unravel the sovereign and humorless, but only ever incompletely, reluctantly, briefly, or accidentally. The silly’s deep conflict with redemption in crisis times is central to this project, which nonetheless insists on sillily flailing with/in media’s small, minor, or otherwise inconsequential details, soaring aimlessly into the silly’s wild nonsovereignty. While the first chapter offers an initial conceptualizing and calibration of the silly and the transqueer in media studies, the remaining three chapters take on specific digital media objects as case studies for thinking transqueerly with silliness. In Chapter 2, I look at irritational aesthetics of silliness in hyperpop music videos by transgender and nonbinary artists, such as SOPHIE and Arca, where abrasive digital modulations produce silly effects in the face and voice, and where silliness is deployed as a transfeminist opacity tactic. In Chapter 3, I turn to the screenlife horror film Unfriended (2014) and its use of the desktop gimmick, which formally exploits the silly exteriorizations of thinking with computers as it playfully refamiliarizes the neoliberal queer politics of the 2010s cultural moment via its confrontationally silly response to and reworking of an early Google ad campaign for the “It Gets Better” movement. In Chapter 4, I explore more aggressively abject forms of silliness in The Eric André Show (2012-), a television comedy series saturated by the intensities of queer negativity, black anality, and often-unfunny forms of silliness, which all interoperate and become uniquely difficult to bear, allowing for ambivalent, unruly, and less-sovereign possibilities that recuperative, representational politics do not. Across these chapters, I turn to silliness at the intersection of form, feeling, mediation, and culture, overall working to trouble its counter/political guarantee. The silly appears, in this dissertation, as neither wholly frivolous nor inherently affirming; rather, it is a contested, ambivalent force that can equally unravel or reinforce our cruel attachments to the normative, to the self-sovereign, and to the promises of good life fantasies.