This article aims to flesh out how Stan VanDerBeek created what Time magazine in 1964 rather glibly described as a curious chapter in the manual of animation'. The main focus is on his pre-computer painted and puppet animation and collage animation works. After considering relevant terminologies, the author explores VanDerBeek's own writings to see how and why his artistic and cultural philosophy could be expressed using animation techniques. After a discussion of a stop-motion puppet film and a painted film, she introduces, via Modernist contexts of collage and photomontage, some of VanDerBeek's many collage and cutout animation films, proposing how his visual neologisms bear comparison with James Joyce's portmanteau technique. She then undertakes an aesthetic and socio-political analysis of his praxis within found footage genres and techniques, and suggests viewer strategies for watching his works. The article concludes by describing some of VanDerBeek's manifold poetics and aesthetics as a curious chapter' within the continuum of political photomontage and independent animation production.