Sydney Chaplin (March 16 1885 - April 16 1965), born as Sidney John Hill, was the elder half-brother of Sir Charlie Chaplin and the half-uncle of the actor Sydney Chaplin (born 1926), who was born as Sydney Earle Chaplin. It is not known who Sydney's father was, although it has been said that it was a man called Hawkes, who never was married to Sydney's mother, Hannah Hill. After her marriage to Charles Chaplin Sr on June 22nd, 1885, Sydney became Sydney John Chaplin.

Sydney and Charlie shared another half-brother through their mother, British actor Wheeler Dryden, whom they did not meet until the 1920s.

Charlie and Sydney Chaplin were very close and looked out for each other from their young days. Though younger, it was Charlie that got onto the stage first, in a play, Sherlock Holmes, but it wasn't long before Syd joined the tour. Fred Karno then signed up Sydney, and he then recommended Charlie, giving him his biggest break. After Charlie left Keystone, he suggested Sydney as his replacement, and he made a few comedies there, including the "Gussle" comedies and the feature-length A Submarine Pirate in 1915.

Soon, he was handling the majority of Charlie's business affairs, negotiating most of his big contracts and appearing in a few films during the First National era. Later films include The Perfect Flapper (1924) with Colleen Moore, A Christie Comedy,Charley's Aunt (1925) and five features for Warner Brothers, 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 most well-regarded film today because of his characterization of cartoonist Bruce Bairnsfather's famous World War I character, Old Bill.

In addition to his inestimable importance in launching and promoting brother Charlie's career over the years, perhaps Syd'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, Co., 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 airplane showroom for their Curtiss airplanes. Emery Rogers conducted the first roundtrip Los Angeles to San Francisco flight in one 24-hour period. Charlie Chaplin took his first-ever airplane ride in one of Syd's planes, as did many other notable personages of the period. Ever the savvy businessman, Syd Chaplin also knew when to retreat from such a venture, right after legislation began to pass regarding pilot licensing and the taxation of planes, flights, and etc.

Sydney Chaplin married twice and had no children. His first wife, Minnie, died in France in September 1936. After World War II, Sydney lived most of his final years in Europe. His second wife, Henriette (called Gypsy) died after Sydney's death. He died on April 16 1965, in Nice, France. His death occurred on his brother Charlie's 76th birthday.

Syd is buried beside his wife Gypsy in Clarens-Montreux Cemetery, near Vevey.

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 (I)."

British film comedian, half-brother of Charles Chaplin.

Entered films with Mack Sennett

Hlaf-brother of Wheeler Dryden.

Son of Hannah Chaplin and Jewish bookmaker Sydney Hawkes, Sr.

Starred on Broadway in "Bells Are Ringing" opposite Judy Holliday (1956) (Tony) and "Funny Girl" opposite Barbra Streisand (1964).

He and Margaret had been engaged for fourteen years.

Son of Charles Chaplin and Lita Grey.

Appeared with his father in Limelight (1952) and Countess from Hong Kong, A (1967).

Romantically linked to Joan Collins (I) during time they were both making Land of the Pharaohs (1955).

Brother of Charles Chaplin Jr.

Half-brother of Geraldine Chaplin, Michael Chaplin (I), Josephine Chaplin, Victoria Chaplin and Christopher Chaplin (I).

Longtime owner/manager of "Chaplin's", a popular restaurant in Palm Springs, California.

Unlike his famous father, Sydney Chaplin is primarily a stage actor who has made only occasional film appearances.

Stepson of Oona Chaplin (I). He is some six weeks her senior.

Won Broadway's 1957 Tony Award as Best Supporting or Featured Actor (Musical) for "Bell Are Ringing."

Was nominated for Broadway's 1964 Tony Award as Best Actor (Musical) for "Funny Girl."