I'm all for learning more about the historical roots and overall development of Western culture, but one should keep in mind that the sheer amount of notable works that have been described as "classics" and "Great Books" is absolutely humongous; this list is of course highly selective and will necessarily be missing a lot of interesting stuff. In general, most people will probably want to focus on the narrower subtopics that specifically draw their interest, and perhaps explore the interconnections among works in that area.