As an African American poet living and writing at the end of the nineteenth century and early twentieth century, the life of the poet himself intersects with the voice of the narrators in these poems.

Dunbar constructed an extended metaphor in the poem "Sympathy," using a caged bird to demonstrate the oppression of African Americans. He understands the feelings of the caged bird because he, too, longs for the freedom he can see beyond the bars of his metaphorical cage; yet he can't quite escape the societal chains which hold him. The cage, then, represents the constructs that prevent the speaker from enjoying the full liberties of being a free American citizen. Note that the caged bird has beaten his wings on the cage until they are bloody, conjuring images of violence inherent in the denial of freedom. Yet despite his injuries, the bird continues beating his wings, longing to escape the cage which confines him. This is the fundamental desire of his soul and the deepest prayer of his heart.

"We Wear the Mask" is somewhat similar. In this poem, themes of oppression are evident, and the speaker again longs for the freedom to exist fully as himself. Yet in this poem, the speaker uses the metaphor of a mask, explaining that he must continually appear content with his situation in order to exist within the constructs of his society. In this poem, his anger and frustration aren't as readily evident to those who confine him; he smiles to cover up his bleeding heart and is thus able to function in a world that would rather ignore his "tears and sighs."

The message of both poems is somewhat similar: those who are oppressed will continually long for freedom, and relying on a resilient spirit provides the ability to continue to persevere toward a more hopeful future.