What was Fitzgerald trying to accomplish by repeatedly mentioning the glasses of Doctor T. J. Eckleburg?
The sign was a way to symbolize all the attention the elite class got, and how they were always being watched. In the first time it is described, it is said to rise above the fog and is able to be seen by many in the surrounding area. Later, after the trouble with Myrtle and the car, his sign is again mentioned, only this time it is referred to by Wilson, who seems to hold the idea that it is "God" and is always watching. Specifically, that he is watching Myrtle with her affair, and that he knows and will punish her for it. Wilson takes it too far, but it does go to show that there is a lot to be seen and watched, with the affairs and underhanded business that goes on in the area.
How effective was Fitzgerald's use of character to portray his theme?
Considering it appears that Fitzgerald's theme has to do with looking back at the past, and how the characters he use all seem to be stuck in the past for one reason or another, I would say it was very effective. In effect, Fitzgerald is dwelling on the one girl who turned him down because he was too poor, and this book goes to show that. Gatsby is his stand in, constantly stuck in the past, one that can never be real again. Tom is the typical, or at least at first, stereotype of the jerk jock who is otherwise perfect. However, Fitzgerald throws a twist in that all of the characters are portrayed sympathetically by the end of the book, at least for a moment (for Tom, literally just a moment.) It also goes to show that sticking in the past hurts everyone: Gatsby dead, Tom and Daisy in shambles, with Nick and Jordan no better or worse than they started, if only for the fact that they were both friends with those affected.
What is Fitzgerald's reasoning for making Gatsby what he is (hero, anti-hero, villain)?
Gatsby is, in my opinion, a tragic hero. His downfalls all come back to the fact that he is stuck in the past, and all of the bad things that he does/did can be linked to that fact. He got into somewhat shady business so that he could be more successful and as such gain Daisy's affection again, like they'd been prior to him leaving for the war. This, of course, mirrors Fitzgerald in that Fitzgerald would be sympathetic with him, seeing as how Gatsby is a sort of stand in for himself, in a way. At least, in that he gets turned down by the woman he loves because he doesn't have enough money, and then when he does have money, there's still no way of regaining her affection for real. This makes people feel sorry for him, while all the same it gets across Fitzgerald's point that it's useless to be stuck in the past, and that the only person it hurts is oneself.
How effective was Fitzgerald's use of Gatsby as a stand in for himself?
It was effective in that it showed just how useless it is to be stuck in the past. With Gatsby, the issue was that he couldn't move on, and after he had managed to pull himself up to Daisy's level and she still found herself unable to truly reciprocate in the way that Gatsby remembered it being, he just couldn't imagine that she didn't feel the same way as him. It managed to show the reader just how hopeless Fitzgerald felt that dwelling on the past could be, and Gatsby's death was the cherry on the top of everything, in that it was symbolic. Everything in Gatsby's life had been leading up to his reunion with Daisy, and after she could not be what he wanted, it only shows that Gatsby would die. Even more so, his death was in part caused by his refusal to let go of his attachment to Daisy.
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