ABSTRACT While in social history and mobilities research, the study of railway mobility is becoming increasingly popular, offering new insights into (trans)national railway cultures, there is less interest in illicit mobility, unconventional modes of travel and non-regulated, irregular patterns of movement, such as train hopping, and the way they function in experimental film. To fill this gap, I build on the recent mobilities literature to discuss two stylistically distinct experimental films, Reading Canada Backwards (Steve Topping, 1995) and Portland (Greta Snider, 1996), which offer a social commentary on train hopping, typically associated with the history and material conditions of North American railway travels. Challenging the larger freighthopping mobilities discourse, both films confront the historical legacy of the hobo, as reimagined by occasional transients and punk drifters, as a product of capitalist enterprise, railroad transportation services and failed bourgeois masculinity. While in narrative and documentary films, hobo culture often emerges as an alternative, intrepid lifestyle and a personal philosophy based on economic or environmental concerns, Reading Canada Backwards and Portland take a more critical and ironic take on riding the rails, highlighting its casual spontaneity, playful creativity and affective potential, which questions the drifter as an active agent of marginal mobility practices.