You don't need to rank strictly and linearly. An objective ordering need not exist. It's enough to see that on shortlists of "great" works, common themes emerge. Is The Great Gatsby better than The Catcher in the Rye? It doesn't matter. They both come with universal acclaim, and that's stiff competition for anything new. Besides, are great works not promoted as being timelessly relevant to the state of the world?
And I loved Catcher in the Rye, but not so much The Great Gatsby. I've found this "shortlist" of classics that have universal acclaim has always been hit or miss for me. The classics I was assigned to read in high school would seem to lurch from riveting to a slog to get thorough. I don't blame the books, it's just what captures my particular interest. Given that, I have never really used "the classics" as a guarantee that I will find the reading fulfilling over other, more obscure, recommendations that I may receive, whether they be old books or new.
I've felt this before. A librarian taught me a trick: chug the book. You were probably trained to really analyze what you're reading, look for symbolism, etc, but you can enjoy a book as almost an emotional-sensory experience instead.
I read both twice, once in high school and again a few years after I graduated (this was over 15 years ago). I loved The Great Gatsby even more (that opening first page is magnificent), and couldn't help but feel like The Catcher in the Rye as being so incredibly naive and juvenile. The latter experience is similar to reading (or watching) Fight Club and thinking Tyler Durden is a hero of sorts and something to aspire to, which is not the ultimate lesson.
Stan Lee made a comic about how he and his co-workers made comics, and in one frame he says something like "How dare it he say it is hackneyed? I stole it from the best classic I could find!" That is, if superhero movies sell today, stories about Hercules and Theseus sold 2500 years ago.
