Sydney John Chaplin was an English actor. He was the elder half-brother of Sir Charlie Chaplin and served as his business manager.
Chaplin was born to 19-year-old Hannah Hill in London. Hannah claimed Sydney's father was a man named Sydney Hawkes, but his father's identity was never verified. The Chaplin surname was adopted following his mother's marriage to Charles Chaplin, Sr., a year after his birth.
While Syd and brother Charlie were in the Cuckoo Schools in Hanwell following his mother's mental collapse, Syd was placed in the program designed to train young boys to become seamen, 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 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 was to fight 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 that was to be the only time that Syd was able to outdo his brother—at least in front of an audience.
After Charlie achieved worldwide fame in the 1910s, the brothers discovered they had another half-brother through their mother, Wheeler Dryden, who had been removed from his mother's care as an infant and brought up abroad by his father. Wheeler was also an actor, and the brothers reunited in Hollywood in 1918, occasionally working together at Chaplin's studio through to the 1950s.
As Charlie was negotiating his Keystone contract, he suggested Sydney 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 comedy short 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 decided to leave the screen to negotiate Charlie a better contract. After getting him a $500,000 contract with Mutual on 27 February 1916, he got him his first million dollar ($1.25 million) contract on 17 June 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 characterization 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 dialogue, "coffee", although there are those who disagree.
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 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 and by 1930 he was declared bankrupt.
In addition to his importance in launching and promoting brother Charlie's career over the years, perhaps Chaplin's most important contribution to history is in the field of aviation. In May 1919, he, along with pilot Emery Rogers, formulated the first privately owned domestic American airline, the Syd Chaplin Airline Company, based in Santa Monica, California. Even though the corporation lasted only a year, in that time it accumulated many "firsts." Syd and partners had the first ever aeroplane showroom for their Curtiss aeroplanes. Emery Rogers conducted the first roundtrip Los Angeles to San Francisco flight in one 24-hour period. Charlie Chaplin took his first-ever aeroplane flight in one of Syd's planes, as did many other notable personages of the period. Chaplin got out of the aviation business right after legislation began to pass regarding pilot licensing and the taxation of planes and flights.
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 one month after his 80th birthday, on 16 April 1965, in Nice, France. Chaplin is buried beside his wife Gypsy in Clarens-Montreux Cemetery, near Vevey.