Racism can be discussed as a pain of the American society that is reflected in music, art, and literature because of the people’s need for expressing their feelings on racial oppression and discrimination. In this context, jazz as a music style that began to develop in the 1920s became the most racially colored musical movement in the United States. In 1929, Fats Waller and Andy Razaf wrote the song “(What Did I Do to Be So) Black and Blue” like the reflection of their existential pain associated with the problem of racism. The song was performed in the most ironical manner in the Broadway show “Hot Chocolates.” However, the song became a jazz standard after the performance of Louis Armstrong, who paid more attention to focusing on the deep emotions and soreness of the blacks hidden in this song. In this context, it is important to answer the question of why Armstrong’s variant of “(What Did I Do to Be So) Black and Blue” is usually discussed as the declaration of the problem of racism in the United States. The extreme popularity of the song among the black population can be explained with references to the fact that Armstrong changed the original lyrics to accentuate the social meaning of the composition and elaborated the sound; still, the uniqueness of the song performed by Armstrong is in his ability to tell the social and personal story of racism in musical terms. The song was composed by Fats Waller for “Hot Chocolates,” and this song was originally performed by Edith Wilson. It is important to state that the song was composed in order to entertain the public of the show and to make the audience laugh at the fate of blacks. Dutch Schultz, the sponsor of the show, expected to hear the humorous lyrics that could demonstrate the feelings of miserable blacks. That is why Andy Razaf chose to focus on representing the personal feelings of the dark-skinned woman who suffered significantly because of being alone in the world of blacks. The comic words were supported with sorrowful tunes, and the combination of different moods really made the public laugh. However, the song acquired a new meaning when it was interpreted and recorded by Louis Armstrong. It is important to state that Armstrong was one of the most talented trumpeters of the discussed musical era, and his songs attracted the attention of the wide public. As a result, Armstrong’s variant of the song’s words made a significant resonance among the white and African American audiences. The words proposed by Louis Armstrong variant influenced each African American because the musician presented the problem as related to all blacks’ hopes and sufferings. In his lyrics, Razaf concentrated on the comic story of the African American girl who felt loneliness because of being black, and the author directly focused on the problem of intra-racial prejudice because it was the matter for discussing in the white elite circles. Thus, Edith Wilson sang in the show about the personal pain of the black woman who stated, “Browns and yellers, all have fellers, / Gentlemen prefer them light, / Wish I could fade, can’t make the grade, / Nothing but dark days insight”. Nevertheless, Armstrong chose to remove that verse, and he emphasized the general idea of racial discrim