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Even in Chaplin’s day there were tricks employed to create different scenes. Here’s how he did the rollerskating stunt in Modern Times. Does this give you any ideas?
http://i.giphy.com/3o7TKvVYIjPhAd1sY0.gif
Modern Times is a 1936 comedy film written and directed by Charlie Chaplin in which his iconic Little Tramp character struggles to survive in the modern, industrialized world. The film is a comment on the desperate employment and financial conditions many people faced during the Great Depression, conditions created, in Chaplin’s view, by the efficiencies of modern industrialization. The movie stars Chaplin, Paulette Goddard, Henry Bergman, Tiny Sandford and Chester Conklin/
Modern Times was deemed “culturally significant” by the Library of Congress in 1989, and selected for preservation in the United States National Film Registry. Fourteen years later, it was screened “out of competition” at the 2003 Cannes Film Festival.
Wikipedia