Focusing on user-generated annotations, this chapter explores the interplay between videographic, embodied, and annotational memories. Examples of video annotation in the contexts of pedagogy, documentation, and ethnography are introduced. An autoethnographic approach provides the basis for examining the mechanics of annotation and the experience of becoming-with in these contexts. Drawing from Gilbert Ryle’s and Clifford Geertz’s concept of thick description, video annotation is characterised as an iterative process towards thick layering that encourages deep reading and the production of difference.