Young Al ran away from home again to join Rich and Hoppe's Big Company of Fun Makers before performing for the 15th Pennsylvanian Volunteers during the Spanish American War.
It was his first experience singing to what was to become his favourite audience, the US serviceman. At one point he even joined the circus.
As depicted in The Jolson Story (1946) young Al sang from the balcony joining in the acts of both Eddie Leonard and Agnes Behler. His first appearance onstage though had been just before this in the appropriately titled Children of the Ghetto which opened at the National Theatre, Washington DC on 18th September 1899.
In 1900 Al joined the Victoria Burlesquers as part of the team of "Master Joelson and Fred E. Moore". Fred and his wife Lillian almost became the young lad's unofficial guardians over the next few years but in 1903 the 17 year old's voice began to break and briefly he had to give up showbusiness and return to Washington DC.
Al sulked around the Yoelson home until his brother Harry suggested they join forces in an act called The Hebrew and the Cadet. In the act Harry was the comedian, Al the straight man. This continued for a year until in 1904 Ren Shields offered the Joelson (as they were then known) brothers the opportunity to join with another vaudevillian Joe Palmer in an act he had written called "A Little of Everything". Not having seen their act Sheilds had made Al not Harry the comedian but he was too young to play anything else.
To advertise the act cards had to be printed but the Joelson brothers name proved to be too long for the cards. It was suggested that they drop the "e" and they decided to give it a go.
When they got a booking it was the first time the public saw a performer called Al Jolson.
Al was uncomfortable in his new role as comedian until James Francis Dooley a blackface monologuist on the same bill suggested he try burnt cork. Blackface was like a mask you could hide your problems behind. It worked, in blackface Al had more confidence than ever before.
Al Jolson had truly arrived.