Asa Yoelson was Jewish. He was born in the village of Serednike, near Kaunas in Lithuania, which then was part of the Russian Empire. He was the fifth and youngest child of his family.
In 1891, his father, who was qualified as a rabbi and cantor, moved to New York City to secure a better future for his family.
By 1894, his father Cantor Moses Yoelson could afford to pay the fare to bring his wife and their four children to the United States.
By the time they arrived—as steerage passengers on the SS Umbria arriving at the Port of New York on April 9, 1894—he had found work as a cantor at Talmud Torah Congregation in the Southwest Waterfront neighborhood of Washington, DC, where the family was reunited.
Jolson's mother, Naomi, died at the age of thirty-seven in early 1895, and he was in a state of withdrawal for seven months. He spent time at the Saint Mary's Industrial School for Boys, a progressive reformatory/home for orphans in Baltimore.
After being introduced to show business in 1895 by Al Reeves, Asa and his brother Hirsch became fascinated by it, and by 1897 the brothers were singing for coins on local street corners, using the names "Al" and "Harry." They often used the money to buy tickets to the National Theatre. They spent most of their days working different jobs as a team.
In the spring of 1902, Jolson accepted a job with Walter L Main's circus. Although Main had hired him as an usher, Main was impressed by Jolson's singing voice and gave him a position as a singer during the circus's Indian Medicine Side Show segment. By the end of the year, the circus had folded, and Jolson was again out of work.
In May 1903, the head producer of the burlesque show, "Dainty Duchess Burlesquers," agreed to give Jolson a part in one show. He performed "Be My Baby Bumble Bee," and the producer agreed to keep him, but the show closed by the end of the year.
He avoided financial troubles by forming a vaudeville partnership with his brother Hirsch, a vaudeville performer known as Harry Yoelson. The brothers worked for the William Morris Agency. Jolson and Harry formed a team with Joe Palmer. During their time with Palmer, they were able to gain bookings in a nationwide tour. However, live performances were falling in popularity as nickelodeons attracted audiences; by 1908, nickelodeon theatres were dominant throughout New York City. While performing in a Brooklyn theatre in 1904, Jolson began performing in blackface, which boosted his career. He began wearing blackface in all of his shows.
In late 1905, Harry left the trio after an argument with Jolson. Harry had refused his request to take care of Joe Palmer, who was in a wheelchair.
After Harry's departure, Jolson and Palmer worked as a duo, but were not particularly successful. By 1906 they agreed to separate, and Jolson was on his own. He became a regular at the Globe and Wigwam Theatre in San Francisco and was successful nationwide as a vaudeville singer. He took up residence in San Francisco, saying the earthquake-devastated people needed someone to cheer them up.
In 1908, Jolson, needing money for himself and his new wife, Henrietta, returned to New York. In 1909, his singing caught the attention of Lew Dockstader, the producer and star of "Dockstader's Minstrels." Jolson accepted Dockstader's offer and became a blackface performer.
According to Esquire magazine, JJ Shubert, impressed by Jolson's overpowering display of energy, booked him for the show, "La Belle Paree," a musical comedy that opened at the Winter Garden in 1911. Within a month Jolson was a star.
And the rest is history!