“My God, what did I do? Was I the Al Jolson of androgyny?”

Said Julia Sweeney, quoted in "Who Is Julia Sweeney Coming to Terms With? It’s Pat/The 'Saturday Night Live' character has been used as an insult for decades. Sweeney and some of her most prominent critics address the enduring legacy of her role" (NYT).

Wasn't Pat worse than what Al Jolson did? Seems to me Pat was an intentional effort at encouraging the audience to feel revulsion and engage in mockery against a kind of person who is an outsider.

From the Wikipedia article, "Al Jolson":

Jolson often performed in blackface makeup. Performing in blackface makeup was a theatrical convention of many entertainers at the beginning of the 20th century, having its origin in the minstrel show. According to film historian Eric Lott:

"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 gaité de coeur that were the prime components of white ideologies of black manhood."

In the retrospective view of a later era, however, the use of blackface has come to be viewed as implicit racism. Music critic Ted Gioia, commenting on Jolson's use of blackface, wrote:

"Blackface evokes memories of the most unpleasant side of racial relations, and of an age in which white entertainers used the makeup to ridicule black Americans while brazenly borrowing from the rich black musical traditions that were rarely allowed direct expression in mainstream society. This is heavy baggage for Al Jolson.

Historians have described Jolson's blackface and singing style as metaphors for Jewish and black suffering throughout history. Jolson's first film, The Jazz Singer, for instance, is described by historian Michael Alexander as an expression of the liturgical music of Jews with the "imagined music of African Americans," noting that "prayer and jazz become metaphors for Jews and blacks." Playwright Samson Raphaelson, after seeing Jolson perform his stage show Robinson Crusoe, stated that "he had an epiphany: 'My God, this isn't a jazz singer', he said. 'This is a cantor!'" The image of the blackfaced cantor remained in Raphaelson's mind when he conceived of the story which led to The Jazz Singer.

Upon the film's release, the first full-length sound picture, film reviewers saw the symbolism and metaphors portrayed by Jolson in his role as the son of a cantor wanting to become a "jazz singer":

Is there any incongruity in this Jewish boy with his face painted like a Southern Negro singing in the Negro dialect? No, there is not. Indeed, I detected again and again the minor key of Jewish music, the wail of the Chazan, the cry of anguish of a people who had suffered. The son of a line of rabbis well knows how to sing the songs of the most cruelly wronged people in the world's history.

According to Alexander, Eastern European Jews were uniquely qualified to understand the music, noting how Jolson himself made the comparison of Jewish and African-American suffering in a new land in his film Big Boy: In a blackface portrayal of a former slave, he leads a group of recently freed slaves, played by black actors, in verses of the classic slave spiritual "Go Down Moses". One reviewer of the film expressed how Jolson's blackface added significance to his role:

When one hears Jolson's jazz songs, one realizes that jazz is the new prayer of the American masses, and Al Jolson is their cantor. The Negro makeup in which he expresses his misery is the appropriate talis [prayer shawl] for such a communal leader.

Many in the black community welcomed The Jazz Singer and saw it as a vehicle to gain access to the stage. Audiences at Harlem's Lafayette Theater cried during the film, and Harlem's newspaper, Amsterdam News, called it "one of the greatest pictures ever produced." For Jolson, it wrote: "Every colored performer is proud of him."