In The White Boy Shuffle, Mrs. Kaufman's decision to move the family from sunny Santa Monica to the hellish Hillside always struck me as odd, but I couldn't quite pin down why. She gives a reasonable enough explanation; the kids are being raised very similarly to Janie in Their Eyes Were Watching God, in which we can see problems arising from African-Americans being raised outside of their culture. Logan says at one point that Janie's refusal to work is a sign of how she was spoiled, and needed to bring herself down from her high chair. Ostensibly, this is what Mrs. Kaufman fears in Gunnar and the girls; she wants them to experience the full meaning of being black in America, and that means moving to the ghetto. But, still it strikes a strange chord, like something wasn't right in moving from the nice neighbourhood to the run-down one. But, I pushed it to the back of my head, thinking that this was merely a show of my naivete, in that everybody should always aspire to be like me and live the way I do.
It was some time later that it finally dawned on me why precisely the move seemed so precisely bizarre. The truth is, Beatty is inverting the somewhat common trope of "the one who made it out," where generally speaking a character leaves a place that others don't particularly want to live in but don't leave for family or lack of money. That is, the character moves out of the ghetto into some nicer place (a more lucrative job, college, suburbia, whatever). Will in The Fresh Prince of Bel-Air is a good example of this; his mom sends him to live with his rich uncle and aunt in a nice California neighbourhood after he gets in a fight with some gangsters in Philadelphia. Another example would be the Freemans in The Boondocks, who move from Chicago to Woodcrest, the epitome of white suburbia. Even Bigger Thomas does this to a degree in Native Son: although he neither moves out of the south side of Chicago nor leave it at all, he still takes a job in affluent Hyde Park as a chauffeur rather than something "on the wrong side of the tracks," presumably like his old job as a commercial driver.
So, why specifically is Gunnar going against the grain here? What is Beatty trying to say by thrusting Gunnar the opposite direction of how this is "supposed to go"? In a sense, it almost seems like he's condemning those who leave the ghetto for bigger and better places. Gunnar is the model of success within his new home; despite a rough start, he eventually makes friends with Scoby, becomes a great poet, and discovers his basketball ability. He wouldn't have done any of these things in Santa Monica; in fact, nothing about his younger years there contribute positively to these occurrences. He earns the respect of Scoby by loudly throwing away the traditionally "right" thing to do (deliver his monologue perfectly) and by embracing his new home (interspersing his new speech with phrases indigenous to Hillside). He begins to think about poetry right after this, and largely as a consequence of this -- his invented monologue is very much a vision of what's to come in his poems. Moreover, the informational background that Gunnar has for his poems isn't something he learned in any school; he's shown to be very auto-didactic, reading old classics in his tent in the department store. And his basketball ability seems to be raw talent; he'd never even played before Hillside, only learning the rules. Back in Santa Monica, he didn't really have anything comparable to his successes in Hillside; he had friends, but they weren't like Scoby. None of them were black, and Gunnar at some points keeps his interests in people like the Tuskegee airmen hidden because it wouldn't seem as cool as the fact that Hitler was missing a testicle. His actions amounted to mere hooliganry in Santa Monica, while Hillside at least had seriously positive moments. Beatty later more conclusively points out how unwelcome black people seem to be in the nicer neighbourhoods with the Harvard recruiter, who claims Hillside and its residents (not realizing Gunnar lives there) to be irredeemable in its awfulness. The white crowds boo Scoby and Gunnar during their games playing for Boston University, while "all of Harlem" comes to see them and cheer them on against Columbia. It certainly fits with the theme of the novel, that these were times so difficult and heavy for African-Americans that they were better off killing themselves than going on trying to live. This strengthening of the idea in the novel that black people who leave their assigned place are doomed to suffer the consequences certainly bodes badly for general race relations. And, the inversion of a common trope brings the reader's attention to this issue subconsciously, such that you hardly notice its very real effect.
Gunnar's "downward mobility" (the opposite of the Jeffersons' "movin on up" and so many other examples you cite) has a connection to Janie's story on another level, too. Even when she lives in Eatonville with Joe, she isn't quite part of the community--the sense that she's "spoiled" (against her will) persists. Moving into the realm of migratory agricultural labor with Tea Cake, and proving to herself, him, and the others on the muck that she doesn't think she's "above" them, becomes an important part of her development of identity. Likewise, Gunnar has to "prove himself" to the Hillside community--and Scoby is his "guide" in a way that's sort of similar to Tea Cake. When Scoby warns him to "stay black" as he boards the bus for El Campesino, it's analogous in some ways to the challenge Mrs. Turner poses when she tries to flatter Janie for her "white" features.
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