Sydney John “Syd” Chaplin (16 March 1885 — 16 April 1965) was an English actor. He was the elder half-brother of Sir Charlie Chaplin and served as his business manager. In May 1919, along with pilot Emery Rogers, he formulated the first privately owned domestic American airline, the Syd Chaplin Airline Company, based in Santa Monica, California. Charlie Chaplin took his first-ever aeroplane flight in one of Syd’s planes, as did many other notable personages of the period. Chaplin got out of the aviation business right after legislation began to pass regarding pilot licensing and the taxation of planes and flights.