This article presents a conceptual and methodological framework that focuses on the interactivity, creativity, and variability of Holocaust images in digital media. Our argument unfolds in three stages. First, we introduce the concept of playful images: historical images that undergo recontextualisation, serving memetic, personal, and interactive engagements in and by digital media. Secondly, drawing on pivotal scholarship in digital methods, anthropology, sociology, and visual analysis, we identify a lacuna in contemporary methodologies and provide a rationale for an innovative approach to visual memory analysis in digital media that considers both digital media affordances and the appropriation of visual and historical materials in digital media. For that purpose, we thirdly outline a visual walkthrough method (VWM), a pragmatic performance of our approach tailored for analysing interactive digital experiences featuring playful images. By examining the playful appropriation of historical images in the video game Call of Duty: WWII (2017), we demonstrate how the interactive experience of playful images can be analysed with the help of the VWM. We conclude by discussing the position of our proposed conceptual and methodological framework within media and memory studies in the digital age.