Career
As Charlie was negotiating his Keystone contract, he suggested Sydney be asked to join the company. Syd and Minnie Chaplin arrived in California, then, in October 1914 and he made a few comedies there, including the "Gussle" comedies and the feature-length A Submarine Pirate in 1915, which, second to Tillie's Punctured Romance, was the most financially successful comedy Keystone ever made.
Following this success, Chaplin decided to leave the screen to negotiate Charlie's Mutual contract. He was able to get Charlie his first million dollars in early 1916. Soon, he was handling the majority of Charlie's business affairs, including a failed sheet music business and a successful merchandising one, in addition to further contract negotiation. He also appeared in a few films during the First National era, such as Pay Day and The Pilgrim. Sydney achieved his own million-dollar contract from Famous Players-Lasky in 1919, but a series of problems resulted in only one failed film, King, Queen, Joker and disappearance from the screen once again. Later films include The Perfect Flapper (1924) with Colleen Moore, A Christie Comedy, Charley's Aunt (1925) and five features for Warner Brothers, including The Man on the Box (1925), Oh, What a Nurse! (1926), The Missing Link (1927), The Fortune Hunter (1927), and The Better 'Ole (1926). The last is perhaps his best-known film today because of his characterisation of cartoonist Bruce Bairnsfather's famous World War I character, Old Bill and the fact that it was the third Warner Brothers film to have a Vitaphone soundtrack.
Sydney's first film for British International Pictures (BIP), A Little Bit of Fluff (1928), proved to be his final film. In 1929, just as was to begin work on a second film for the studio, Mumming Birds, he was accused of biting off the nipple of actress Molly Wright in a sexual assault. BIP settled out of court, conceding the truth of Wright's claims. Following the scandal, he left England, leaving a string of unpaid tax demands. By 1930 he was declared bankrupt.
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