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Herman E. Calloway is first introduced to the reader on a blue flyer Bud carries around in his suitcase: “HERMAN E. CALLOWAY and the Dusky Devastators of the Depression!!!!!!” He is the band’s leader and the person whom Bud thinks must be his father. When Bud meets Calloway at the Log Cabin, Calloway’s testy character is on full display. He rejects any notion that he could be Bud’s father and promises to send Bud back to where he came from. It’s evident he doesn’t get along well with the people around him, and behind his back, the band members are quite open about what a cantankerous grump he is.

Early in the story, Bud had described the one picture he had of his momma when she was a little girl. Momma had told him “that hardheaded man,” Bud’s grandfather, had insisted she wear “that horrible hat.” Bud comes to discover, at the end of the story, that the hardheaded man is actually his grandfather, Herman E. Calloway. Bud’s momma (Angela Janet Caldwell) had had a volatile relationship with Calloway. When Bud tells Calloway that his mother is dead, and that Bud is Calloway’s grandson, Calloway’s tough demeanor unravels. He faces the fact that he had been too harsh on his daughter and pushed her away. Calloway’s apology to Bud indicates that deep down he is a sensitive man who cares deeply for his family.