He became a member of the male dance troupe, ‘The Eight Lancashire Lads’ and toured across the music halls in Great Britain, all through 1899 and 1900.
In 1903, he was cast in his first show titled ‘Jim, a Romance of Cockayne’, in which he played the role of a newsboy. The show opened in July that year, in the ‘Kingston upon Thames’ in Southwest London and was not very successful.
From October 1903 to June 1904, he travelled with Saintsbury, and his plays were immensely successful, which lead him to travel to London to act with William Gillette, an actor.
In 1906, he became part of the amateur comedy troupe ‘Casey's Circus’. He performed comedy acts with them and soon rose to prominence. When the troupe finished touring in July 1907, Charlie was left without a job for a few months and lived with a family in Kennington.
In 1910, he played the lead role in the sketch ‘Jimmy the Fearless’, which was an immediate success and soon after he started getting a lot of media attention, which catapulted his fame and popularity.
In 1913, he signed a contract for a period of one year with the New York Motion Picture Company, which promised him a pay of $150 a week.
In 1914, he made his feature film debut with ‘Making a Living’, in which he played, ‘Edgar English’, a womaniser.
In 1914, he appeared in several films for Keystone Studios including, ‘Kid Auto Races at Venice’, ‘Between Showers’, ‘A Film Johnnie’, ‘His Favorite Pastime’ and ‘Tillie's Punctured Romance’.
In 1915, he also directed and wrote films for the Essanay Film Manufacturing Company. Some of them include ‘A Night Out’, ‘The Champion’, ‘The Tramp’, ‘Work’, ‘A Woman’, ‘The Bank’,’ Triple Trouble’ and ‘Police’.
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From 1916 to 1917, he worked for the ‘Mutual Film Corporation’ - he directed, wrote, produced and acted in their films. Some these films included — ‘The Floorwalker’, The Vagabond’, ‘The Pawnshop’, ‘The Count’, ‘The Cure’ and ‘The Adventurer’.
From 1918 to 1923, he made a total of nine films which were distributed by the ‘First National Exhibitors' Circuit’. Some of the films were ‘A Dog’s Life’, ‘The Bond’, ‘The Kid’, ‘Pay Day’, ‘The Pilgrim’, ‘Sunnyside’ and ‘The Idle Class’.
From September 26, 1923 onwards, he released his films under the United Artists label. He directed, acted, produced, wrote and composed tunes for many of these movies.
In 1925, his Academy Award winning film ‘The Gold Rush’, which he directed, starred in and produced, was released. It is one of his classics and most memorable films.
In 1928, his film ‘The Circus’ was released. In this 70-minute silent film, he played the role of a clown. It was one of his highest grossing silent films.
Released in 1936, one of his most remembered films, ‘Modern Times’, is a satirical portrayal of struggle to cope in the industrialised world. The film is considered one of his most popular silent films.
In 1940, he came up with ‘The Great Dictator’, which was one of his most commercially successful films. He played the role of a Jewish barber in the film.
In 1952, his Academy Award winning film ‘Limelight’ was released. The film was set in London, during the eve of World War I and he played the role of a former clown named ‘Calvero’.
In 1957, he directed and acted in the comedy film ‘A King in New York’, a satirical film about the political and social life in the United States of America. The film was only a moderate success and received mixed reviews.
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Released in the year 1967, ‘A Countess from Hong Kong’, was his last film.