Jolson's first experience with film was back in 1913 for a sequence which was projected onstage as part of the Broadway show The Honeymoon Express. This consisted of a frantic race between a car driven by Gus (Jolson) and a train, it was the finale of Act 1 of the show.


In 1914 Al appeared in a short subject in whiteface which parodied silent movie acting. On 6th May 1918 Jolson and 35 motorcycle policemen filmed a chase sequence for another short for a Policemen's Benevolent Association. It was shown only once at the Winter Garden on 11th May, Al made the film believing all the proceeds would go to charity, when he found out Vitagraph would get 60 % he ordered the film confiscated. 


His first serious attempt at filmmaking involved the great pioneer director D.W. Griffith who had practically invented the silent feature with The Birth of a Nation (1915) and Intolerance (1916). The film was to have been called Black Magic or Black and White.


Al had a screen test in whiteface on 11th June 1923 but wasn't very happy with the results. He said it made him look like a zebra. His astute manager Louis Epstein was against the movie venture. Eppy thought Jolson was popular onstage why risk everything on the movie which might be a disaster ? Al agreed with him when he saw the first rushes and abandoned the film.


Griffith eventually made Black Magic as His Darker Self with Lloyd Hamilton and sued Jolson though his lawyer was unable to prove that Al had  made a firm oral commitment to do the film. Griffith received only $2,627 in damages when he had sued for over $500,000.


On 26th August 1926 Jolson signed with Warner Brothers to do Vitaphone shorts. Vitaphone was a new sound on disc system. On 6th September he filmed Al Jolson In a Plantation Act which included three songs : When the Red,Red Robin Comes Bobbin' Along, April Showers and Rockabye Your Baby with a Dixie Melody. For years the audio of this historic short was thought lost forever but it was recently found and restored to the existing picture.