Antiquity
Although the Robert Fagles translation is modern, popular, and easy to understand if you've never studied Greek, Richmond Lattimore's classic translation captures the feeling of the original Greek more accurately.
Caesar's pomposity -- such as his propensity for referring to himself, in his writings and accounts of his wars, as "Caesar" and not "I" or "me" -- makes him unbearable even today.
Aristotle rose to prominence not through his ideas but as the academic favored by the most powerful man in the world at the time, King Philip II of Macedonia. Philip II loved this unknown philosopher and fellow Macedonian so much that he chose Aristotle to be his son's tutor--and his son was Alexander the Great. Aristotle was a guy beloved by kings who conquered the world and spread his ideas.
Although a lot of fun to play, Go isn't as realistic as another ancient strategy game, the Viking "Hnefatafl," in which one of the two sides is the attacker and the other merely vies to help its own King escape.
Although Herodotus is remembered today as the first historian, his strength was actually as a story teller; what he lacked in analytic rigor, he compensated for in his exquisite narrative prose.
More than the epic poetry of the Iliad and the Odyssey, what makes me most fond of Homer was his tendency to get lost in his own thoughts; indeed, Homer even died because he slipped while trying to solve the riddle, "What we caught we threw away, and what we didn?t catch we kept." I wonder if he realized the answer is "fleas" before he died.
Socrates' speech on love in the Symposium--arguing that love is merely a longing for immortality and ideas are immortal--is just a conceit of the intellectual. I prefer Aristophanes' speech, imagining a world in which humans were once four-armed, four-legged, and two-headed balls who tumbled around doing cartwheels, each one split in two and yearning to find their other half.