The most obvious similarities between the two works are that they both express the adverse circumstances of African Americans in the decades after Emancipation. Paul Laurence Dunbar published "Sympathy" in 1899 while Maya Angelou's I Know Why the Caged Bird Sings (1969) takes place in the 1930s and 1940s during her childhood and early adulthood. Despite the generational gap between these works, the authors' similar experiences of racism and discrimination indicates that little had changed in the time between their comparative experiences. Recall that both of their works concerned the years before the Civil Rights movement.

The title of Maya Angelou's autobiography is taken directly from the line in Paul Laurence Dunbar's poem, so her work was certainly influenced by his writings. Both her autobiography and "Sympathy" contain the metaphor of a caged bird, representing the freedom of white people outside the figurative cage compared to the oppression of African Americans. While the entirety of "Sympathy" is dedicated to this metaphor, its presentation in Maya Angelou's work is comparatively subtle. She builds upon this reference throughout her autobiography. To compare two important excerpts of their two works, beginning with Angelou's statement:

A bird doesn't sing because it has an answer, it sings because it has a song.

Compare this to the following passage in "Sympathy":

But a prayer that he sends from his heart’s deep core,

But a plea, that upward to Heaven he flings