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Diagramming the intersection between the representation of work and the work of representation, this thesis explores how animation has historically mediated technological transformations in film production through its self-reflexive engagement with labour. I track the entanglement between animated images and image production through three key inflection points in animation history: beginning with early animation's pre-industrial roots; continuing through animation's industrial rationalisation; and concluding with a discussion of digital animation. Contrary to claims that animation's self-reflexive address is unique to early animation, I argue that early animation's turn towards self-reflexivity does not vanish with the disappearance of the animator from the frame. Rather, animation showcases an ongoing preoccupation with labour. It works out tensions between autonomy and automation; movement and mechanisation; labour and alienation at key points throughout its history, especially when the work of animation is transformed by its formalisation, rationalisation, and digitalisation as a medium. This thesis is organised into three chapters. Chapter One takes up cinematic reflexivity and self-figuration to critique *Gertie the Dinosaur* (1914 Winsor McCay) through the lens of the operational aesthetic, underscoring how this aesthetic mode poses limits to theories of cinematic disclosure and problematises representations of work in early animation. Taking up the film as a cinematic treatise on the labour of animation, this chapter argues that the film's live-action prologue disregards the role photography played in automating the reproduction of Gertie's animated imagery, electing to prioritise the manual labours of animation as a handicraft. Chapter Two builds on Siegfried Kracauer's theory of the mass ornament to contemplate masses, multitudes, and crowds for film. It decodes the mass ornament in the musical choreographies of Busby Berkeley; addresses its resonances with assembly line production in classical animation; and concludes with a discussion of homogeneity and heterogeneity in the production of digitally simulated crowds. Chapter Three takes up the 'quality assurance guarantee' of Pixar Animation Studios to consider how it articulates its relationship to creativity and the labour of computer animated filmmaking. This chapter investigates Pixar's post-Fordist labour history to ask how this labour history intersects with the broader turn towards the immaterial labours of creativity- labours which the studio uses to underwrite its reputation as 'Creativity, Inc.' Through a critique of its political economy, Chapter Three describes how Pixar curates its public image and optimises worker productivity by indoctrinating animators into a company culture and corporate mythology which foregrounds artistry and creativity over computer-intensive forms of work. Reflecting on animation as a material practice; as an ideology; and through a critique of its political economy, this thesis contemplates the complex configurations between animated imagery; animated film production; and the labour of animation. This interdisciplinary work combines critical methods from production studies, film history, media theory, cultural studies, and animation scholarship to offer incisive contributions to film and media studies. It brings together aesthetic theory with critiques of the technologies, histories, and production methods of animated film. And it raises important questions for film and media studies about the work of animation; animation's mediation of this work; and asks what animation theory can bring to the study of cinematic labour.