Abstract: Rotoscoping of facial features is often an integral part of Visual Effects post-production, where the parametric contours created by artists need to be highly detailed, consist of multiple interacting components, and involve significant manual supervision. Yet those assets are usually discarded after compositing and hardly reused. In this paper, we present the first methodology to learn from these assets. With only a few manually rotoscoped shots, we identify and extract semantically consistent and task specific landmark points and re-vectorize the roto shapes based on these landmarks. We then train two separate models -- one to predict landmarks based on a rough crop of the face region, and the other to predict the roto shapes using only the inferred landmarks from the first model. In preliminary production testing, 26% of shots rotoscoped using our tool were able to be used with no adjustment, and another 47% were able to be used with minor adjustments. This represents a significant time savings for the studio, as artists are able to rotoscope almost 73% of their shots with no manual rotoscoping and some spline adjustment. This paper presents a novel application of machine learning to professional interactive rotoscoping, a methodology to convert unstructured roto shapes into a self-annotated, trainable dataset that can be harnessed to make accurate predictions on future shots of a similar object, and a limited dataset of rotoscoped multi-shape fine feature systems from a real film production.