There is a great joke in Woody Allen's Zelig where the titular character, after spending a lifetime of high and improbable incident, cannot finish Moby Dick. (Slight, non-important spoiler of the movie ahead. The movie's not about it and it won't spoil your high pleasure in it at all.) He tries many times whenever he has the chance to read it, because it's a classic and you're supposed to read classics, but he can never manage it, and his last act before dying naturally with a great life behind him, is, once again, trying and failing to read Melville's masterwork.
The joke gets at the heart of intelligent, curious people—most of us, if not all—trying to be culturally literate. It exposes our cultural insecurity. Why are we insecure? Because ever since long ago, there has been a set of rules about reading that says "You Must Read This" in order to live in and talk about the world. A sacred pile of books that are the Western Canon, that teachers urge on their students, that are the basis of all literature programs in college, that make up great reading lists and books telling you what you should read. We all know what those classics are; we don't need to list them. If we did, they would be too long for this post, too long for the earth, and would stretch far into space. But, we are told, over and over again, we must read them, and know them, because they will improve our hearts and minds, our lives, and, perhaps more importantly, give us social currency, cachet, so that we can impress people. Birds decide mates by how the other dances. The 21st century educated human decides on a mate if the other has read Pride and Prejudice or Middlemarch or George R.R. Martin.
Today is Bloomsday. (Two good explanations and inside info on the book, here and here.). If you're thinking of finally starting Ulysses and have never read Joyce before, I would advise against it. The novel is a bit difficult, and having a hard time with it might put you off reading what else the author wrote. And if you did that, that would deprive you of stories of great beauty.
I don't think anyone should follow the many admonitions of reading list guides by tackling the great works first, as if checking off an accomplished chore, without having read the authors earlier works. Because these are masterworks for specific reasons, and one reason could be stylistic innovation, something in the world of literature that has never been done and written before, a new break with the old guard, a new way of representing the self and the world. It is not true at all that great literature must do this and must be difficult in order to be great, but great literature can take risks, be daring in what it does, and sometimes those risks are difficult to comprehend. The author does not want you to give up on the book because he made it hard. He wants you to be amazed at the new style of experience he set down. He is placing a big bet that that won't turn you off. So to help, it might be a good idea to have read his earlier stuff first. So that you already know him and can trust him when he takes a sharp right turn towards something very new. And also when that turn is too much for some people but doesn't dissuade them from loving his/her other stuff, because they had read it.
When we read fiction this way, when we read authors systematically and chronologically, they become another character in the books. Just as with the fictional character, it becomes easier to note their qualities, find out their personality and interests, and like or dislike them, as we would a character. By reading all the words they wrote, from when they first started writing them to when they finally stopped, we can track their life, and see what mattered to them, and when, and why it stopped mattering (when they wrote about something else) or if it mattered more (when their masterwork is on a subject they had already written about). It enriches, greatly, the reading experience.
And this goes for all the other arts and media. There are these compendium books, "1000 Movies to See Before You Die" or a "1000 Albums to Listen To..." And they have the same potential reward: if we start at the beginning of a film director's oeuvre, or a band's, and then follow them as they produce art, their masterworks will be all that much masterful, and we'll truly be in the know about their art, so that we can truly impress at parties, and maybe, truly find the better mate.
This is easy to say but hard to do. How do you do it? We love to experience randomly, as it comes, when it airs, what's popular at the moment. Making a plan to do this sounds too much like homework, and we all hated homework. And it sounds longer than it actually is. We think that it would take more time than the reading we do now, but, it won't. Just replace all the books you were planning on reading with all the works of Charles Dickens or Ernest Hemingway. And then do what you would have done anyway, what you love to do, because it's art and you love art and want to be an intelligent, curious person.