‘Amos ‘n’ Andy” was one of the most, if not the most popular radio shows in America from the late ’20s through the early ’30s. The show starred two white men portraying two black men. Its popularity is attributed with its relatability to white audiences and its multi-ethnic comic appeal. Of course, today we question the appropriateness of blackface and any cultural appropriate and misrepresentation in general. If it were produced today, this show would not have anywhere near as much appeal as it did back in the ’20s and ’30s or the following to attempt a television revival in the ’50s. When two black men were cast in the parts of Amos and Andy for this purpose, the production was met with protest from the black community and did not receive enough backing to continue production. However, this is not the punchline of Billy’s joke.
In terms of Chicago, this description of the characters will give some insight into what makes the joke funnier than Billy not getting his name right…
“The stereotypical portrayals of Amos Jones and Andy H. Brown were balanced by other attributes. Amos was unquestionably dense and naive, but he was also honest, dedicated and hardworking. And Andy, although lazy, conniving and pretentious as minstrelsy’s venal Jim Dandy, was also a good-natured fellow.”
…So Billy is really more of the Andy.
Watkins, Mel. “What Was It About ‘Amos ‘n’ Andy’?” The New York Times. The New York Times, 06 July 1991. Web. 01 Mar. 2017.