As Charlie was negotiating his Keystone contract, he suggested Sydney Chaplin be asked to join the company, and Syd and his wife Minnie Chaplin arrived in California in October 1914. Syd 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, Sydney Chaplin decided to leave the screen to negotiate Charlie a better contract. After getting him a $500,000 contract with Mutual on February 27, 1916, he got him his first million dollar ($1.25 million) contract on June 17, 1917 with First National. 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 (1921), disappearing 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 Bros. Pictures, 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 second Warner Bros. film to have a Vitaphone soundtrack. It is also believed by many to have the first spoken word of dialog, “coffee”, although there are those who disagree.

Sydney Chaplin’s first film for British International Pictures (BIP), A Little Bit of Fluff (1928), proved to be his final film. In 1929, just as he 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. Sydney Chaplin married twice and had no children. His first wife, Minnie, died in France in September 1936 following surgery for breast cancer. After World War II, Sydney lived most of his final years in Europe. His second wife, Henriette (called Gypsy) survived him. After a long illness, he died childless one month after his 80th birthday, on Good Friday, 16 April 1965, in Nice, France, on his brother Charlie’s 76th birthday. Chaplin is buried beside his wife Gypsy in Clarens-Montreux Cemetery, near Vevey.