Sydney John Chaplin (; 16 March 1885 – 16 April 1965) was an English actor. Chaplin was the elder half-brother of actor and filmmaker Charlie Chaplin and served as his business manager in later life.

Through their mother Hannah, they were older half-brothers to the younger Wheeler Dryden, who grew up separately with his father in England and was not told about his half-brothers until 1915. Dryden later emigrated to the United States, joining the Chaplins in Hollywood. Sydney Chaplin was also a half-uncle of actor Sydney Chaplin (1926–2009), who was named after him.

Sydney Chaplin

Early life

Sydney John Hill was born in London to the unmarried 19-year-old Hannah Hill, who was a music hall entertainer. She claimed the boy's father was Sydney Hawkes, but his father's identity was never verified. Hannah was of Romanichal heritage. A year later, his mother married Charles Chaplin Sr., and the latter became his legal guardian. Sydney's surname was changed to Chaplin. Hannah and Charles had a son together called Charlie.

Sydney Chaplin

While Syd and half-brother Charlie were in the Cuckoo Schools in Hanwell following their mother's mental collapse, Syd was placed in the programme designed to train young boys to become seamen. He served on the Exmouth training ship docked at Grays, Essex. He followed this training period with several years working on ships, receiving high marks from all of his employers but his ambition was to get into the entertainment business like his parents and brother, and he left his final voyage with that in mind.

Sydney Chaplin

In 1905 Charlie and Sydney worked briefly together in one of their first stage appearances, Sherlock Holmes. Syd was briefly cast as a villain in that play. In 1906, however, he landed a contract with Fred Karno, of Karno's London Comedians, and worked hard to bring Charlie into the company two years later. Charlie never achieved the sort of fame Syd did as a principal comedian for that company, but surpassed him later as an actor, director and producer.

After Charlie achieved worldwide fame in 1915, the brothers were contacted by their half-brother Wheeler Dryden, whose father had just told him of the connection. His father had removed Wheeler from their mother as an infant and brought him up separately. Wheeler was also an actor, and the brothers reunited in Hollywood in 1918 after they all immigrated to the United States. They occasionally worked together at Charlie Chaplin's studio through to the 1950s.

Career

Keystone

As Charlie was negotiating his Keystone contract in Hollywood, he suggested that Syd should join the studio. Syd and his wife Minnie Chaplin arrived in California in October 1914.

Syd made a few appearances with the Keystone stock company in supporting roles before starring as a new character, Reggie Gussle. Gussle was a brash, mustachioed, happy-go-lucky fellow who enjoyed flirting with women and sneaking drinks, but was usually under the watchful eye of his large, ominous wife (Phyllis Allen). Syd Chaplin was less frantic than the other Keystone comedians, who usually ran around the scene with exaggerated gestures. Syd's antics were slower but quite energetic. His expressive face was also featured in numerous close-ups, unusual for Keystone stars. His improvisational approach sometimes resulted in scenes running very long -- in one case, so long that the finished scenes were divided into two separate comedies, Gussle's Backward Way and Gussle Tied to Trouble. The Gussle comedies caught on very quickly, and within the year these one-reel, 10-minute comedies were doubled in length. Syd Chaplin made 12 Gussle subjects, and then starred in an extended-length featurette, A Submarine Pirate in 1915. Second to Tillie's Punctured Romance, this was the most financially successful comedy Keystone ever made.

Charlie's business affairs

Following this success, Syd 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 Pictures. Soon he was handling the majority of Charlie's business affairs, in addition to further contract negotiations. Their sheet music business failed, but they were successful with a merchandising one.

Sydney also appeared in a few of Charlie's 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 his making only one, failed, film, King, Queen, Joker (1921). He disappeared from the screen once again.