"They were careless people, Tom and Daisy—they smashed up things and creatures and then retreated back into their money or their vast carelessness, or whatever it was that kept them together, and let other people clean up the mess they had made."
You can't look at modern life without seeing that.
There are exception like The Picture of Dorian Gray although that's very late 19th century--and, of course, Wilde is very accessible.
ADDED: In general, I don't think I read any, but both Fitzgerald and Hemingway seem pretty reasonable for a high school English class. Probably better choices than the like of Catcher in the Rye and A Separate Peace to be honest.
Oh, and forcing anyone to read Melville should be a crime. A very few people I know loved the experience, but I was unable to finish Billy Bud much less Moby Dick.
I vaguely recall not liking Billy Bud in high school although I read Moby Dick as an adult and was mostly glad I worked my way through but it did take an effort.
I don't think I hated Catcher in the Rye at the time. It just didn't make much of an impression one way or the other.
Also Britten's Billy Budd is one of the 2 operas I really love.
1966 BBC version: https://www.youtube.com/watch?v=A1lVBfqQyjs
The rest is history. I'm a voracious reader of "junky" fantasy books.
But Mencken was a real wordsmith -albeit a really, really cynical one.
> and, under it all, the simple sentimentality of a somewhat sclerotic fat woman.
There's more than enough books vying to be classics; do future readers a favor and select one that fulfills BOTH criteria; Well Written and Interesting to Read.
There were some books in high school that I really enjoyed that I'm afraid to reread because maybe they wouldn't stand up for me. I'm thinking about Lost Horizon, The Chrysalids, Brave New World, Canticle for Leibowitz, On the Beach, and Grapes of Wrath.
I did read Brave New World in high school, but it didn't do anything for me until I re-read it a couple years ago.
I liked this one when I read it years ago, but when I tried to re-read it aloud to one of my kids[1] I discovered that most of Hilton's characters' dialog read exactly the same—they have no voice—plus the prose was really clunky to read—uniquely so among the oddball books I read aloud to my young kids, and I read them some a lot older than that, plus a couple contemporary to Hilton's book, so it's not an age-of-the-writing problem. It was so unpleasant to read aloud that I didn't make it past the first chapter. Really soured me on the book.
[1] Hey, when they're young enough, it hardly matters what you're reading to them, may as well be something you want to read, unless you're reading them a picture book.
[EDIT] LOL, actually, now that I think about it, Gatsby was another one I read aloud to one of my kids. No problems with that one.
I just didn't get it. All I see is a bunch of horrible people being stupid and terrible to each other.
I don't doubt that that's a very American thing. I just don't want to read about it, no matter how well it's written.
Inconsistency note: I love doing Shakespeare, even though it's precisely a bunch of stupid people treating each other horribly, but very, very well written.
And I was left wondering whether the two groups of people have had different life experiences. Some have had bitter experience of awful people and it'll never be something to enjoy.
I mentioned a love for Shakespeare in a footnote, something I developed long after high school, despite-not-because-of my high school education. I found my way into it via movies. The same happened with Jane Austen, whom I hated as dumb-people-doing-dumb-things until the right film showed me how it actually was supposed to work.
Conceivably such a thing could exist for Confederacy of Dunces, but I'm not going out of my way to find out.
But to your basic point. I was having a conversation with a college friend about series including Orange is the New Black and others that I don't remember--possibly Breaking Bad. And they just couldn't get into a series where you were supposed to sympathize with people who were basically, well, bad to various degrees. Probably (for whatever reason) some people just don't like anti-heroes in literature or video.
I don't mean to oversimplify; both are complex shows with extraordinary feats of writing and acting. But I felt Better Call Saul was a more interesting take on the anti-hero because it wasn't just horrible people being mean to each other. If nothing else, comparing and contrasting the differences is a good exercise.
It is quite the yarn.
Mencken's critique seems to be that for all the craftsmanship Fitzgerald displays on the page, the story itself is rather thin and contrived. I don't think I'd disagree with that, though it is interesting that we still read (and teach!) this book a hundred years later. It has a hold on the American psyche not just because the writing is superb (some pages are truly astonishing), but because it feels uniquely American. There is still a recognizable reflection even today in the mirror that Fitzgerald holds up in Gatsby.