Sydney Chaplin (1885-1965) was the elder half-brother of Charlie Chaplin.

Charlie and Sydney Chaplin were very close and looked out for each other from their young days. Though younger, it was Charlie that got onto the stage first, in a play, Sherlock Holmes, but it wasn't long before Syd joined the tour. Fred Karno then signed up Sydney, and he then recommended Charlie, giving him his biggest break. After Charlie left Keystone, he suggested Sydney as his replacement, and he made a few comedies there, most notably A Submarine Pirate in 1915.

Soon, he was handling the majority of Charlie's business affairs, negotiating most of his big contracts and appearing in a few films during the First National era. Later films include The Perfect Flapper (1924) with Colleen Moore, Charley's Aunt (1925) and The Better 'Ole (1927).