I have often pored over the list of the 50 worst and 50 best books of the twentieth century by the Intercollegiate Studies Institute. I'm sure that many people could find a favorite book on the worst list, but I maintain that the list is fundamentally sound because it prompted me to find a number of great authors that I would have otherwise neglected, such as Eliot and Toynbee. This also provided me a list of books that I can profitably avoid, which I have generally done so.
I remember when I was first preparing to enroll in college, there were a number of lists of books that literate, educated people ought to have read. I wanted to be one of those, so I tried some of those books. Wow, were those lists terrible! I wasted 2 or 3 years trying to get something out of works that really are not all that good. For example, I read Thoreau and Emerson because they were supposed to be the best American philosophers, exemplars of a homegrown tradition. I tried. I really did. They just aren't that good. Consulting my copy of Human Accomplishment by Charles Murray, I see that Emerson does in fact rank on the list of the most notable philosophers, but with an index score of only 2. The maximum is 100 (who would be Aristotle). Emerson does better in literature, coming in with a score of 11 for literature, and Thoreau 6, but seriously, why waste your time? T. S. Eliot comes in with a score of 32 in literature, and Dante at 62. If you want to get some bang for your buck, you ought to read someone with a justified reputation for being famous.
For the adventurous, you could read someone who does not yet have a reputation, like Charles Sanders Peirce. Edward Oakes S. J. called him the American Aristotle. If you want to read an American philosopher with some heft, Peirce is your man. Peirce's peculiar burst of creativity at the end of his unusual life has made him extremely obscure, but my limited experience with his work has left me very impressed. I would very much like to investigate his work on the third kind of logic, abductive logic, that is very much in line with modern science. Peirce's significant character flaws contributed to his obscurity, but there is much to be learned from him. Now why couldn't the reading lists I got when I was 18 be useful like that?
There are legitimate arguments to be made against canonical works. Perhaps the best is that a canon expands the mind while cramping the imagination. That is not the whole story, but it does have an element of truth in it. However, as T. S. Eliot argued, the greatest innovation is the result of successfully absorbing a great canon.
Looking over the ISI list again 10 years after I first saw it, I can see that I have read quite a number more than I had then. This is a good thing, since my life would be less if there were not a long list of worthy books I have not yet read.
h/t Michael Flynn