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Rome
This is very republic heavy, especially the late republic. I don't necessarily think the late republic is more interesting or important than the foundation of the republic, but we do have far more good sources on the late republic & early empire. Any of the Plutarch biographies can be read in a couple of hours, and those that have survived antiquity are all readily available online in good translations. Sallust's The War With Cataline is also readable in one sitting and is tremendous fun. If you do decide to jump in with these ancient sources, you will find you lack a lot of context. I think you just have to roll with it.
Parallel Lives - Plutarch
Some of my favourite stuff ever written. Maybe the most fun and approachable ancient history. A big collection of short biographies of the leading men of ancient Greece and Rome. The author is a diligent, wise and fair minded Greek philosopher writing around the time of Rome's zenith. He tries to draw moral lessons from the lives of these men - examples of virtues to be emulated and vices to be avoided. He condemns Caesar and Alexander for pride and ambition, for example, but cannot prevent himself from enjoying their exploits and excesses. A few centuries ago you would be considered a complete ignoramus if they you were not thoroughly familiar with the lives. Plutarch was of immense importance to the Founders, French revolutionaries etc. You cannot understand Napoleon, Jefferson, Hamilton, Robespierre and co. without having read Plutarch. The lives of the Grachii are a great place to start. if you are unfamiliar with Roman history and prepared to take the plunge, the life of Caesar is a good place to start if you want something that you are (probably) at least a little familiar with. If you are feeling more Greek start with Themistocles, which is the best of the bunch IMO. https://penelope.uchicago.edu/Thayer/e/roman/texts/plutarch/lives/home.html - here are all the surviving lives freely available, courtesy of the university of Chicago. Penguin and Oxford have very good collections on the late Roman republic, and prime Athens.
The Aeneid - Virgil
Imperial Rome needed an epic poem in the vein of the Homeric epics. The Robert Fagles translation is very good. Very much a product of its time and important to Augustus politically, lenses to keep in mind when reading it.
The Metamorphoses - Ovid
More Imperial Roman poetry. Very interesting and peculiar, especially if you haven't read anything comparatively ancient before. It's not a narrative like The Aeneid so you can just dip into some of the poetry and get a feel for it.
The War With Catiline - Sallust
Brilliant near contemporary account of the Catiline conspiracy - an attempt to overthrow the republic by a gang of wretches led by a few brilliant rogues. This episode of Roman history is paid much less attention than it should be, overshadowed by later events. Sallust is super biased, which is something to keep in mind, but its great. Can be read in one sitting.
The Decline and Fall of the Roman Empire - Edward Gibbon
Classic History. As important for its influence on the way we write history as for its inherent value. Gibbon does not hold your hand. It is enormously long so I have only yet read it in abridgement. If you want entertainment start with the parts about Atilla the Hun, if you want to hear Gibbons description of Rome at its height and analysis of the fall in short read the first few chapters.
The Roman Revolution - Ronald Syme
Brilliant but serious and difficult history of the fall of the republic/ rise of the empire. Wouldn't go for it unless you are already familiar. It's more his analysis of events, presuming a certain preexisting familiarity with events in the reader. It was written against the backdrop of the rise of fascism in the 30s and it bears that mark. Augusts/Octavian is the main character. This book really makes you appreciate how much of a genius and bastard he was.
From the Grachii to Nero - Howard Hayes Scullard
If you want to get into Rome, want something modern, and don't know where to start this is the book for you. It also has a lot for those already well acquainted. A standard textbook.
The War with Hannibal - Livy
Greece
Parallel Lives - Plutarch
See my list for Rome above for an explanation. In terms of the Greeks I would start with the life of Themistocles.
The Ancient Athenian Plays
Any of the Athenian tragedies can be read in a few hours. Oedipus Rex by Sophocles is absolute dynamite. Try to do it in one go, without distraction. We all know what is coming, and have done for a very long time, but it's still incredibly compelling. Antigone about Oedipus’ Daughter/half sister is also brilliant, though not as well known. The Oresteia by Aeschylus is a trilogy of tragedies, a weekend of reading and best read consecutively and uninterrupted. All the Athenian tragedies are mental, very interesting and very good reads. They allow you to step into the minds, morality and worldview of a completely alien culture. The classics remain classics because they still resonate with us, but they are also worth reading for how deeply strange they are: they allow us to step into a wholly alien, outrageous but complete civililsation. We get something similar from Homer's depiction of Achilles treatment of Hectors corpse, or Odysseus and the Suitors, but that feels less disconcerting because at that time the Greeks were savage. But Athens is the fount of western civ. It seems so wrong, at first, that they were so different to us. The core value of the tragedies is that by reading them carefully (and you really should try at least one from each of Sophocles, Aeschylus and Euripides) we can begin to actually understand.
The Iliad and The Odyssey - Homer
The argument I would use to convince a sceptic to read these is the magnitude of their impact on everything that came afterwards. These are the ur-texts of western literature; essentially every educated person of the last 2500 odd years was throughly familiar with both, from Alexander sleeping with the Iliad under his pillow to yank hockey players reading the Odyssey at the last winter Olymics. Knowing these epics will bring a lot more life to other works, and not just books. If you walk into a random old building anywhere in Europe there's a good chance you will find references in sculpture or paint to episodes from Homer. Aside from that they are tremendous works in their own right (Duh! They wouldn't have survived for two and a half millennia, painstakingly and lovingly transcribed and transmitted by dozens of generations, scribes with quills twitching by candle light, monks fleeing barbarians with only time to grab a few precious items, and you don't even have the gratitude to read them!) Fagle's translations are the best modern translations in English. I have tried others. One very popular and very recent translation is not worth a moment of your time, it is so far from the spirit of the original. The Iliad comes first chronologically, but I think the Odyssey is more fun and more interesting, so probably a better place to start.
Anabasis - Xenophon
Xenophon was a student of Socrates and contemporary of Plato. This is his account of going to Persia, with the disapproval of his teacher, to fight as a mercenary for a want-to-be emperor. He gives a first hand account of his leadership of his fellow Greek mercenaries, after their leaders had been treacherously massacred, from the far side of Arabia back to the Mediterranean. A kind of ancient heart of darkness/apocalypse now.
Histories - Herodotus
The father of history Literally the first history book in the sense that we understand the term, and what a great first effort. The focus is supposed to be the war to keep the persians out of greece, but he takes forever to get there One example of an anecodte in there thats been borne out... sailors south of the equator
Five Best Self Improvement Books
For the hustlers
The Electric Kool Aid Acid Test
Teaches the value of conformity
Waiting for Godot
Teaches the value of impatience
The Symposium - Plato
Teaches the proper position of romance
The Táin
Teaches the value of friendship
The Myth of Sisyphus
Teaches the imporance of the Grindset
Five Favourite Novels
Anna Karenina - Leo Tolstoy
Don't want to put both this and War and Peace. I know these can seem intimidating given their length and the fact they are "serious" 19th century Russian stuff written by a man with a terrifying beard, but they are just so brilliant. Anna Karenina is more conventionally a novel, war and peace is a big monster sprawling all over the place. But I love both. The good news is Tolstoy tends to write in short chapters and is constantly moving between his different narrative threads, so they are very rarely hard reading. With war and peace you may have to commit to giving it one hundred pages or before it really sucks you in.
Brideshead Revisited - Evelyn Waugh
For me the best novel written by an Englishman since the first world war. Did not know anything about it before I picked it up, so I won't say anything more.
The Sun Also Rises
At some point in my teens, having only read history for a few years, I decided to read a proper novel to see what they were all about. I went into the Easons on shop street and recognised the name Hemingway, so I started here. Hemingway is great, (For Whom the Bell Tolls is also a banger, and he has many great short stories), but this is still my favourite of his. Simultaneously uber macho and uber romantic, stylish, exotic, exciting.
The Brothers Karamazov
Yes I am pretentious. Surely one of the best novels ever written, but I do prefer Tolstoy.
Non-History Non Fiction
pretty self explanatory
The Electric Kool Aid Acid Test & The Right Stuff - Tom Wolfe
Two super journalistic near novels by Wolfe. The first follows a group of Hippies rampaging around the west in the late 60s, just as the wave was breaking. The second is about American test pilots competing for positions on the first space flights. They are both exciting, fun, serious works. Wolfe's style is masterful and completely unique and he is worth reading for those reasons alone, but his eye for character and superb, absurd situations are equally fantastic. I think the Right Stuff is better, but go with whichever topic is more interesting to you.
The Making of the Atomic Bomb - Richard Rhodes
A Time of Gifts - Patrick Leigh Fermor
A History of Western Philosophy - Bertrand Russell
Civilisation - Kenneth Clarke
Might be one of the only cases where the TV series is better than the book. When the BBC was moving to colour in the 60s Mr Clarke was given a very long leash to make a series about western culture from the dark ages to the then present. If you're the type to watch youtube while eating, watch this. There is nothing else like it.
Plays
Romeo and Juliet
Bit of a niche one this one... We forget how good he is because we're constantly told he is the goat, and he is, but he did earn the reputation. This is my favourite of his, I haven't seen it in person yet, but even as a read it is beyond description great.
Macbeth
Another obscure one
Short Works
Fear and Loathing in Las Vegas - Hunter S. Thompson
Goated - read the original rolling stone piece.
Meditations on Moloch - Scott Alexander
Night - Elie Wiesel
Memoir by a survivor of Auschwitz. Brilliant writer, very short, read in one go for maximum gut punch.
20th Century History
A gnarly century fr
The War that Ended Peace - Margaret MacMillan
Brilliant book, read it while deciding what to study in college, so maybe I shouldn't be reading it (damn you MacMillan). About the outbreak of WWI, very much focused on the why and how the war started. Carefully lays the diplomatic chess board,
A People's Tragedy: The Russian Revolution, 1891–1924 - Orlando Figes
A masterpiece history of the Russian Revolution. The term "important" is greatly overused, this work deserves it.