I've seen some folks saying that the reference to The Great Gatsby in TBOB was just a joke Alex didn't put deeper meaning into—which might be true, IDK the man's motives for choosing Gatsby specifically—and that there's no way the book has any deeper relevance to Bill's character beyond the eye doctor thing—which is totally wrong. Whether or not Alex intended parallels, there ARE parallels. So, for those of you who didn't read or didn't pay attention to The Great Gatsby:
the book's about a guy who started out as an unimportant loser with starry-eyed dreams, who very quickly gained a lot of power/gold and now presents himself as this dapper fancy well-dressed super important guy.
He constantly throws huge parties, he's got a reputation for being THE party host. But it's a sham, he's pouring all these resources into this party to make himself look so cool but he's living at the very edge of his means.
He lies about his history, lies about how he got his money (spoilers: he's a criminal), lies even in how he presents his personality—he's a con artist, he's always wearing a mask.
The reason he's doing all this—putting on the mask, making himself look so great—is because he's trying to reach across this very thin boundary to a better life he can see, JUST out of reach, so close but something he's never quite clever enough and rich enough and persuasive enough to reach. Every night at his parties he stares at his goal, he can LITERALLY SEE it, he just can't reach it himself.
The best he can do is briefly charm and dazzle someone on the other side of this social boundary, but he can never quite persuade that person to help him cross over; in fact no one on the other side of the boundary thinks he has a right to cross it.
He finds somebody—the guy narrating the book about him—who's very lonely, socially awkward, and disillusioned, whom he can easily awe with his stories and persuade to help him reach his goal, come on please, it'll be harmless! (It is not harmless.)
He loses control over the act he's putting on and over the people who only follow him around as long as he's still got the resources to keep them entertained and loyal.
It ends with him getting murdered by a guy he has LITERALLY never met before—by which point everyone has realized that he's a nobody making it all up as he goes along who was just desperately chasing the illusion of a good life and the admiration of everyone around him.
The narrator ends up disillusioned with him and the whole culture around him of grasping and clawing for a glitzy glamorous life at the expense of the regular people who are manipulated, trampled, and discarded in the process.
Now tell me that Gatsby doesn't have any parallels to Bill's character. And this is just based off reading the book a decade ago—there's probably tons of little details I don't even remember. The book may well have been chosen as a coincidence, it did recently hit the public domain. But if so, it's a VERY GOOD coincidence.
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