Al Jolson (May 26, 1886 – October 23, 1950) was an American singer, comedian and actor. In his heyday, he was dubbed "The World's Greatest Entertainer". He was born in Russia (now Lithuania) and emigrated to America at the age of five with his Jewish parents.

His performing style was brash and extroverted, and he popularized a large number of songs that benefited from his "shamelessly sentimental, melodramatic approach". Numerous well-known singers were influenced by his music, including Bing CrosbyJudy Garland, rock and country entertainer Jerry Lee Lewis, and Bob Dylan, who once referred to him as "somebody whose life I can feel". Broadway critic Gilbert Seldes compared him to "the Great God Pan," claiming that Jolson represented "the concentration of our national health and gaiety."

In the 1930s, he was America's most famous and highest paid entertainer. Between 1911 and 1928, Jolson had nine sell-out Winter Garden shows in a row, more than 80 hit records, and 16 national and international tours. Although he's best remembered today as the star in the first (full length) talking movie, The Jazz Singer, in 1927. He later starred in a series of successful musical films throughout the 1930s. After a period of inactivity, his stardom returned with the 1946 Oscar-winning biographical film, The Jolson Story. Larry Parks played Jolson with the songs dubbed in with Jolson’s real voice. A sequel, Jolson Sings Again, was released in 1949, and was nominated for three Oscars. After the attack on Pearl Harbor, Jolson became the first star to entertain troops overseas during World War II, and again in 1950 became the first star to perform for G.I.s in Korea, doing 42 shows in 16 days. He died just weeks after returning to the U.S., partly due to the physical exertion of performing. Defense Secretary George Marshall afterward awarded the Medal of Merit to Jolson's family.

According to the St. James Encyclopedia of Popular Culture, "Jolson was to jazz, blues, and ragtime what Elvis Presley was to rock 'n' roll". Being the first popular singer to make a spectacular "event" out of singing a song, he became a “rock star” before the dawn of rock music. His specialty was building stage runways extending out into the audience. He would run up and down the runway and across the stage, "teasing, cajoling, and thrilling the audience", often stopping to sing to individual members, all the while the "perspiration would be pouring from his face, and the entire audience would get caught up in the ecstasy of his performance". According to music historian Larry Stempel, "No one had heard anything quite like it before on Broadway." Author Stephen Banfield agrees, writing that Jolson's style was "arguably the single most important factor in defining the modern musical . . ."

He enjoyed performing in blackface makeup – a theatrical convention since the mid-19th century. With his unique and dynamic style of singing black music, like jazz and blues, he was later credited with single-handedly introducing African-American music to white audiences. As early as 1911 he became known for fighting against anti-black discrimination on Broadway. Jolson's well-known theatrics and his promotion of equality on Broadway helped pave the way for many black performers, playwrights, and songwriters, including Cab Calloway, Louis Armstrong, Duke Ellington, Fats Waller, and Ethel Waters.

Al Jolson was born as Asa Yoelson in Seredžius, Lithuania, (Yiddish: סרעדניק, Srednik) then in the Kovno Governorate of the Russian Empire, the fourth child of Moses Reuben Yoelson and his wife Naomi. His siblings were Rose, Etta, Hirsch (Harry), and a sister who died in infancy. Moses Yoelson moved to the United States in 1891, and was able to find a job as a rabbi and cantor at the Talmud Torah Synagogue in the Southwest Waterfront neighborhood of Washington, D.C. Three years later, his family would join him.

Hard times hit the family when his mother, Naomi, died in late 1894. Following his mother's death, young Asa was in a state of withdrawal for seven months. Upon being introduced to show business in 1895 by entertainer Al Reeves, Asa and Hirsch became fascinated by the industry, and by 1897, the brothers were singing for coins on local street corners, using the names "Al" and "Harry". They would usually use the money to buy tickets to shows at the National Theater. Asa and Hirsch spent most of their days working different jobs as a team.:23-40

In the spring of 1902, he accepted a job with Walter L. Maim's Circus. Although he had been hired as an usher, Maim was impressed by Jolson's singing voice and gave him a position as a singer during the circus' Indian Medicine Side Show segment.:49-50

By the end of the year, however, 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. Asa gave a remarkable performance of "Be My Baby Bumble Bee", and the producer agreed to keep him for future shows. Unfortunately, the show closed by the end of the year. Asa was able to avoid financial troubles by forming a vaudeville partnership with his brother Hirsch, now a vaudeville performer who was known as Harry Yoelson. The brothers worked for the William Morris Agency.:50-60

Asa and Harry also eventually were teamed with Joe Palmer. During their time with Palmer, they were able to get bookings in a nationwide tour. However, live performances were fading in popularity, as nickelodeon theaters captured audiences; by 1908, nickelodeon theaters were completely dominant throughout New York City as well. While performing in a Brooklyn theater in 1904, Al decided on a new approach and began wearing blackface makeup. The conversion to blackface boosted his career and he began wearing blackface in all of his shows.:61-80

In the fall of 1905, Harry left the trio, following a harsh argument with Al. Harry had refused Al's request to take care of Joe Palmer — who was in a wheelchair — while he went out on a date. After Harry's departure, Al and Joe Palmer worked as a duo, but were not very successful together. By 1906, the two agreed to separate, and Jolson was on his own.:68-70

Al became a regular at the Globe and Wigwam Theater in San Francisco, California, and remained successful nationwide as a vaudeville singer He took up residence in San Francisco, saying the earthquake-devastated area needed someone to cheer them up. In 1908, Jolson — needing money for himself and his new wife Henrietta — returned to New York. In 1909, Al's singing caught the attention of Lew Dockstader, who was the producer and star of Dockstader's Minstrels. Al accepted Dockstader's offer, and became a regular blackface performer.:70-81

According to Esquire magazine, "J. J. Shubert, impressed by Jolson’s overpowering display of energy, booked him for La Belle Paree, a musical comedy which opened at the Winter Garden in 1911. Within a month Jolson was a star. From then until 1926, when he retired from the stage, he could boast an unbroken series of smash hits."