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Performing in blackface makeup was a theatrical convention used by many entertainers at the beginning of the 20th century, having its origin in the minstrel show. Most early American stage actors performed with the aid of costume and makeup, often as characters of other nationalities and races. Al Jolson was the most famous performer to wear blackface makeup when singing which is now considered a form of racial stereotyping. However, by the standards of stagecraft a hundred years ago it was considered no more than another stage costume or prop.[40]

In addition, working behind a blackface mask "gave him a sense of freedom and spontaneity he had never known before and was not considered racially offensive in the early 1900s."[41] According to some historians, for the white minstrel man "to put on the cultural forms of 'blackness' was to engage in a complex affair of manly mimicry...To wear or even enjoy blackface was literally, for a time, to become black, to inherit the cool, virility, humility, abandon, or gaite' de coeur that were the prime components of white ideologies of black manhood." [42]:52

Jolson first saw African-American music, such as jazz, blues, and ragtime, played in the back alleys of New Orleans. He enjoyed singing the new jazz-style of music, and it's not surprising that he often performed in blackface, especially songs he made popular, like Swanee, Mammy, and Rock-A-Bye Your Baby With A Dixie Melody. In most of his movie roles, however, including a singing hobo in Hallelujah, I'm a Bum or a jailed convict in Say It With Songs, he chose to act without using blackface. In the 1927 film The Jazz Singer, he performed only a few songs, including My Mammy, in blackface, although there was nothing in the storyline that required a black singer.

Some IMDB reviewers feel that Jolson's use of blackface was partly intended as an act of anti-racism by his groundbreaking solo performances of black music on the American stage. As a Jewish immigrant and America's most famous and highest paid entertainer, he clearly had the incentive and resources to help break down racial attitudes. For instance, the Ku Klux Klan (KKK) during its peak in the early 1920s, included about 15% of the nation's eligible population, 4-5 million men. While D.W. Griffith created the blockbuster movie The Birth of a Nation, which glorified white supremacy and the KKK, Jolson chose to star in The Jazz Singer, which defied racial bigotry by introducing American black music to white audiences worldwide. [43]

While growing up, he had many black friends, including "Bill 'Bojangles' Robinson, who later became a legendary tap dancer." [44] As early as 1911, at the age of 25, he was already noted for fighting discrimination on the Broadway stage and later in his movies:[45]

    * he promoted the play by black playwright Garland Anderson, [46] which became the first production with an all-black cast ever produced on Broadway;
    * he brought an all-black dance team from San Francisco that he tried to feature in his Broadway show;[45]
    * he demanded equal treatment for Cab Calloway with whom he performed a number of duets in his movie The Singing Kid.
    * he was "the only white man allowed into an all Black nightclub in Harlem;" [45]
    * he once read in the newspaper that songwriters Eubie Blake and Noble Sissle, neither of whom he had ever heard of, were refused service at a Connecticut restaurant because of their race. He immediately tracked them down and took them out to dinner "insisting he'd punch anyone in the nose who tried to kick us out!" NY Times

Brian Conley, former star of the acclaimed 1995 British play Jolson, stated during an interview, "I found out Jolson was actually a hero to the black people of America. At his funeral, black actors lined the way, they really appreciated what he’d done for them." [47] Noble Sissle, then president of the Negro Actors' Guild, represented that organization at his funeral.[48]

According to the St. James Encyclopedia of Popular Culture: "Almost single-handedly, Jolson helped to introduce African-American musical innovations like jazz, ragtime, and the blues to white audiences.... [and] paved the way for African-American performers like Louis Armstrong, Duke Ellington, Fats Waller, and Ethel Waters.... to bridge the cultural gap between black and white America." [43] Jazz historian Amiri Baraka wrote, "the entrance of the white man into jazz...did at least bring him much closer to the Negro."[49]:151 He points out that "the acceptance of jazz by whites marks a crucial moment when an aspect of black culture had become an essential part of American culture."[50]

In a recent interview, Clarence 'Frogman' Henry, one of the most popular and respected jazz singers of New Orleans, said, "Jolson? I loved him. I think he did wonders for the blacks and glorified entertainment."