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Syd Chaplin biography – Charlie’s older brother

Biography of Sydney Chaplin (March 16, 1885 – April 15, 1965)

Sydney Chaplin is best known for being Charlie Chaplin‘s older brother, who led Charlie into life in the theater. He later became Charlie’s business manager and co-worker in many of Charlie’s films — but Syd’s life contained more that that.

Sydney was born in London, England, UK on March 16, 1885.   His mother was Hannah Chaplin, and his father is presumed to be Sidney Hawkes, a Jewish bookkeeper. However, there is no record of a marriage certificate between Hannah and Mr. Hawkes.   When Hannah married Charles Spencer Chaplin later that year, Sydney assumed the last name of Chaplin.   His half-brother, Charlie Chaplin, was born in 1889, and Sydney behaved as Charlie’s protective older brother for the rest of his life.

Syd Chaplin: A BiographyShortly after Hannah gave birth to Wheeler Dryden (after an affair with Leo Dryden), her husband divorced her. Wheeler was raised by his biological father.  Sydney and Charlie lived with Hannah, their young lives in a cycle of poverty, and Hannah’s recurring bouts with mental illness led to the boys’ being taken into the custody of the state several times.

During these times, young Sydney trained to be a sailor at the Harnell School and worked as a seaman after his graduation.  He returned to take care of his younger brother.   Sydney’s heart was on the stage, however, and he became an actor. At one point he got a role in the play Sherlock Holmes (1905) — where his brother Charlie also got a role as the page boy.   The next year, Sydney won a position with Fred Karno’s famous troupe, Karno’s London Comedians.  Two years later, he fought to help Charlie gain a position there as well.   He succeeded, and the boys were both successful stage comedians in England.  Until Charlie was hired (after an American tour) by Mack Sennett for the Keystone Film Corporation, where Charlie began making silent movies.

In 1914, Charlie Chaplin returned the favor and had Keystone hire Sydney Chaplin for the movies.   Sydney and his wife, Minnie, moved to California, U.S.A. where Syd made many short films for Keystone. These included Dough and Dynamite (1914) (with Charlie Chaplin), the “Gussie” series of shorts, and in 1915 A Submarine Pirate — Keystone’s second-highest grossing film, after Tillie’s Punctured Romance.

In 1916, Syd put his acting career on hold to become his brother Charlie’s business manager, negotiating his million dollar contract with Mutual Film Corporation.   In addition to future negotiations, Syd took responsibility for other aspects of Charlie’s income. These included licensing for merchandise, and the unprofitable “The Charlie Chaplin Music Publishing Company” as well.

1918 was a very busy year for Sydney Chaplin. He co-starred with his brother Charlie in Shoulder Arms as Kaiser Wilhelm. Syd repeated the role in the patriotic film The Bond with Charlie.  The Bond was used to help sell Liberty Bonds for the war effort during World War I.   Sydney also appeared with Charlie in his classic short film, A Dog’s Life.   On a personal note, Charlie and Sydney also met with their half-brother, Wheeler Dryden, now an adult actor who came to work with Charlie Chaplin as well.

In 1919, Syd Chaplin entered a very different business as he created the first domestic airline in the U.S.A. — The Syd Chaplin Airline Company.   Charlie took his first flight on his brother’s airline, as did many other celebrities. However, Syd sold out the business after a year, due to government certifications and regulations.   Still in show business, Syd signed his own million dollar contract, with Famous Lasky Players. Syd was also central in the creation of United Artists.

Syd continued making films, including King, Queen and Joker (1921) and Payday (1922) with his brother Charlie. He also had several roles in Charlie’s classic silent film, The Pilgrim (1923).   From 1925 to 1926, he made several feature films for Warner Brothers.  This included his final film, A Little Bit of Fluff (1928).

Sadly, Syd’s career came to an end in 1929, with the accusation of sexual assault against a movie co-worker.   He left England, and in 1930 declared bankruptcy.   In 1935 (1936 in some accounts), his first wife, Minnie, died from complications from breast cancer surgery.   He later remarried, and he and his second wife, Henriette (also known as Gypsy), stayed together until his death.   Neither marriage resulted in children.

After World War II, Syd and Gypsy lived most of their remaining life together in Europe.   After a long illness, Syd dies on April 16, 1965, in Nice, France. Ironically enough, Syd passed away on his brother Charlie’s 76th birthday.   Syd Chaplin is buried beside Gypsy in Clarens-Montreux Cemetery, near Vevey.

Trivia about Syd Chaplin

  • Darryl F. Zanuck, who worked for Syd Chaplin for a couple of years in the 1920s, referred to him as “the greatest ladies’ man in Hollywood history — better even than Errol Flynn.”
  • He was the uncle of Charles Chaplin Jr., Sydney Chaplin, Geraldine Chaplin, Michael Chaplin, Josephine Chaplin, Victoria Chaplin, Eugene Chaplin, Jane Chaplin, Annette Chaplin, Christopher Chaplin and Spencer Dryden.


Computer nerd by day, professional clown on evenings and weekends (Raynbow), who combines the two by maintaining a bunch of websites dedicated to the history and performances of clowning, such as Free Clown Skits, and comedy such as Best Clean Funny Jokes.

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