If I were setting up a dissident reading list for the Classics, I’d do something like this. I’d break it down by the five W’s: Who, What, When, Where, and Why, with a total difficulty rating and a further breakdown of “what” by “necessary” vs. “nice to have,” and probably a “you probably think this is necessary, but it isn’t” section. Here’s an illustration.
Meditations, by Marcus Aurelius.
Difficulty: Easy. You can beneficially read Meditations even if you know next to nothing. You’ll get more out of it the more you know, of course, but it’s the closest thing ancient philosophy had to a how-to manual.
Who: Marcus Aurelius, Roman Emperor in the mid-late 2nd century AD. The last of the “Five Good Emperors,” Marcus spent much of his time dealing with barbarian incursions and plague. There are some good biographies of the man, but Wiki covers the high points.
What: Because of the above, the Meditations were something like Marcus’s private self-help manual. He’s reminding himself to remain literally Stoic in the face of serious, seemingly unsolvable problems.
When: Late 2nd century AD. Greco-Roman philosophy was well-developed at this point; Stoicism was part of the classical tradition.
Where: In general, the European part of the Roman Empire. Specifically, on campaign against the barbarians – Marcus wrote a lot of the Meditations at the front.
Why: Because this man was the richest, most powerful individual in his world… and hated it. As a Stoic, he believed that virtue was its own — and, indeed, the only — reward, but as Roman Emperor he was forced to do un-virtuous things all day every day. It’s good instruction for how to live with yourself — how to be a man in a world that so often forces you to act like a snake.
Essential Background: Not much beyond the above.
Nice to have: The basics of Stoic doctrine. Specifically, their belief that “living virtuously” and “living according to nature” were basically synonymous, and that they were the only way to true happiness. A little Stoic epistemology, too — as their way of life depends on seeing the true nature of things, their standards for knowledge (what we’d call “justified true belief”) are extremely high. A statement like “pain is indifferent” is clear, and useful, on its own, but knowing the Stoic view of knowledge helps one appreciate just how prevalent the “indifferents” are, and how tough being truly indifferent is. Also nice to know: The wholesale adoption of Marcus by medieval Christians. There’s a very strong Stoic streak in Christianity’s first 1500 years; Marcus is always up there with the very best of the “virtuous pagans.”
None of these are necessary, though — you could lightly edit the Meditations (taking out the “thank you’s” at the start of Book One, explaining a few allusions) — and publish it today as a self-help manual. Also not necessary: Any real background in ancient philosophy. Back then, “philosophy” meant “a way of living,” not “a system for investigating the world.” Since Marcus is convinced of Stoicism’s truth, he doesn’t spend any time engaging the doctrines of other schools.
That’s an easy one. Here’s a hard one:
Leviathan, by Thomas Hobbes.
Who: English Royalist during the Civil Wars (his side lost).
What: A defense of unlimited royal power as the only defense against violent anarchy and civil war.
When: The nastiest phase of the Period of the Wars of Religion, 1517-1648. Specifically, right after the Thirty Years’ War (1618-48).
Where: Early Modern England.
Why: What’s government for, anyway? Are we doomed to keep fighting forever if we can’t figure out the One True Faith? What makes a government legitimate, and what happens if the government loses its legitimacy?
Necessary background: The Wars of Religion. What divine right monarchy is. The basic issues at stake in the Reformation. The background of the Scientific Revolution, as Hobbes’s method doesn’t make sense without it. The political background leading up to the Civil Wars.
Nice to know: Basic Aristotelianism (Hobbes is against it). The context of international law (e.g. Grotius). Contemporary continental thought about legitimacy (Bodin etc.). Machiavelli, both the Prince and the Discourses (the great-grand-daddies of all modern political thought). The course and outcome of the Thirty Years’ War, especially the end stage (Richelieu and raison d’etat). How and why Hobbes came home under the Protectorate.
Unnecessary: The details of contemporary science (as opposed to the method, which is essential knowledge). In other words, you don’t need to know the specifics of Hobbes’s mechanical worldview, since they’re wrong — sight and memory don’t work like he says they do — but you absolutely have to know that he considered himself first and foremost a natural scientist. The military details of the Civil War, or the politics of the Protectorate.
Overall difficulty: Pretty hard. Hobbes is a clear writer; his language is a bit archaic, but you’ll get used to it fairly quickly. As Hobbes is the pivot point for an entire worldview, though, it’s hard to grasp the background material. You’ll need to have a lot of outside information… and, of course, the ideas themselves are quite challenging.
Feel free to add your own in the comments. Let’s start compiling the list!