The son of the cantor of the Talmud Torah Synagogue (now Ohev Sholom Talmud Torah) in Washington, D.C., Jolson became a popular singer in New York City in 1898, and gradually developed the key elements of his performance: blackface makeup; exuberant gestures; operatic-style singing; whistling and directly addressing his audience.

By 1911, he had parlayed a supporting appearance in the Broadway musical La Belle Paree into a starring role. He began recording and was soon internationally famous for his extraordinary stage presence and personal rapport with audiences. His Broadway career is unmatched for length and popularity, having spanned close to 30 years (1911-1940). However, he is best known today for his appearance in one of the first "talkies" The Jazz Singer, the first feature film with sound to enjoy wide commercial success, in 1927. In The Jazz Singer Jolson performed the song "Mammy" in blackface. In truth, Jolson's singing was never jazz, indeed his style remained forever rooted in the vaudeville stage at the turn of 20th century.

"Jolie" as he was known to his friends in "The Show Business" was the first entertainer to sell one million records. While no official "Billboard" chart existed during Jolson's career, their staff archivist Joel Whitburn used a variety of sources such as Talking Machine World's list of top-selling recordings, and Billboard's own sheet music and vaudeville charts to estimate the hits of 1890-1954. By his reckoning, Jolson had the equivalent of 23 #1 hits, the 4th-highest total ever, trailing only Bing Crosby, Paul Whiteman, and Guy Lombardo. Whitburn calculates that Jolson topped one chart or another for 114 weeks.

Among the many songs popularized by Jolson were "You Made Me Love You," "Rock-a-Bye Your Baby With A Dixie Melody," "Swanee" (songwriter George Gershwin's first success) "April Showers" "Toot Toot Tootsie Goodbye" "California, Here I Come" "When the Red, Red Robin Comes Bob-Bob-Bobbin' Along" and "Avalon".

He was a political and economic conservative, supporting Calvin Coolidge for President of the United States (with the ditty "Keep Cool with Coolidge") unlike most other Jews in the arts, who supported the Democratic candidate, John William Davis, who lost to Coolidge in 1924.

He was married to actress/dancer Ruby Keeler from 1928 to 1940 when they divorced; they had adopted a son, Al Jolson, Jr., during their marriage but when he was 14 the boy changed his name to Peter Lowe after his mother's second husband, John Lowe.

After leaving the Broadway stage Jolson starred on radio, and his shows were typically rated in the top ten. However, Jolson scored what many believe to be the greatest comeback in show business history when Columbia Pictures produced the film biography The Jolson Story in 1946, which starred Larry Parks as Jolson, lip-synching to Jolson's voice. Jolson himself made a short appearance in the film. A box office smash (it was the highest grossing film since Gone with the Wind) led to a whole new generation who became enthralled with Jolson's voice and charisma. Despite such singers as Frank Sinatra, Bing Crosby, and Perry Como being in their primes, Jolson was voted the "Most Popular Male Vocalist" in 1948 by a Variety poll.

His legacy is considered by many to be severely neglected today because of his use of stage blackface, at the time a theatrical convention used by many performers (both white and black), but today seen by many as a racial slur. Jolson was billed as "The World's Greatest Entertainer", which is how many of the greatest stars (including Bing Crosby, Frank Sinatra, Judy Garland, Elvis Presley, Mick Jagger, Rod Stewart, Jackie Wilson) referred to him. A life-long devotion to entertaining American troops, servicemen and women (he first sang for servicemen of the Spanish-American War as a boy in Washington, D.C.) led him, against the advice of his doctors, to entertain the troops in Korea in 1950 when his heart began to fail.

He died on October 23, 1950, in San Francisco, California at the age of 64, evidently of a heart attack, and was interred in the Hillside Memorial Park Cemetery in Culver City, California. On the day he died, Broadway turned off its lights for 10 minutes in his honor.

Al Jolson has three stars on the Hollywood Walk of Fame:

For his contribution to the motion picture industry at 6622 Hollywood Blvd.; For his contribution to the recording industry at 1716 Vine Street; For his contribution to the radio industry at 6750 Hollywood Blvd.

Forty-four years after Jolson's death, the United States Postal Service acknowledged his contribution by issuing a postage stamp in his honor. The 29-cent stamp was unveiled by Erle Jolson Krasna, Jolson's fourth wife, at a ceremony in New York City's Lincoln Center on September 1, 1994. This stamp was one of a series honoring popular American singers, which included Bing Crosby, Nat King Cole, Ethel Merman, and Ethel Waters. Al Jolson is one of Mr. Burns' (from The Simpsons) favorite actors - Mr. Burns still believes him to be alive. Jolson's song I'm Sitting on top of the World was played during the opening montage of 1930's New York in the 2005 remake of King Kong.