Over time, the term “bootlegging” has evolved beyond illegal copyright infringement and moonshine to describe, in essence, a creative act. Debates about homage, appropriation, and theft—which previously felt comfortable in the academic context of the art world—are being reimagined in the worlds of corporate branding, social media, and the creative industry as a whole. Bootlegging has become fetishized within creative fields as an aesthetic in and of itself, influencing everything from underground record labels to DIY T-shirts, publishing ideologies to acts of high fashion détournement. For many designers, the term seems to resonate with our impulse to exhume the past, our ongoing quest for production and transmission of meaning, and a desire to both participate in and critique the broader industries that commodify the artistic act. It also begs a variety of questions regarding two ideas that are both core to a museum’s mission: history and context. How might the idea of bootlegging relate to a cultural institution’s brand and design practice? Is it possible to bootleg ourselves as a means of archiving our legacy while contextualizing it in the present? Can strategies be developed in which organizations leverage their past in generative and unruly ways to better understand who they are? What happens when a visual identity is thrust into uncomfortable and potentially illicit scenarios? We found our internal conversations touching on everything from copyright, politics, and race to maker culture, fandom, and memes. To get some insight into contemporary culture’s obsession with bootlegging, we turned to designers and artists who exploit this phenomenon in their various practices.