Sydney John Chaplin (; 16 March 1885 – 16 April 1965) was an English actor. Chaplin was the elder half-brother of actor and director 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. 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. 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. 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