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Man, I dunno, I tend to agree that Rushmore is his best (at the least, it has had the most influence on me), but I think it's a very close thing between it and The Royal Tannenbaums. (But after that there is certainly a large gap to the next best.)

I agree that could be a stretch but Rushmore does not only depict a nerd but one that is creative and iconoclast. Many times we have a bond with a movie for personal reasons that are not shared with the rest. I shared my ranking where there are movies which are classical top and others personal takes. That is the reason to create these (non algorithmic/AI) lists: share and help others to move from the average^average.
No Bottle Rocket?

I think that is the best.

It's certainly the most raw and personal, to its benefit, but it's too unpolished to be as great as the others.

I wish he had remade it like a decade ago, after honing his style and technical talents, and with a right-sized budget. I'd still go see it if he did a remake now, but I doubt it would maintain enough of its spark at this point :)

I’m drawn to rawness. I think the acting performances is what really appeals to me. I don't think a remake could capture those.

Royal Tenanbaums is really polished and well done.

Right, one of the many great things about Rushmore is that it is a mix of these. It's amazingly polished for someone's second movie. Like, that aspect of it shocks me every time I watch it. But it also still has a lot of that raw soul that Bottle Rocket does.
I will watch Rushmore tonight.

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