Start with Xenophon, which is what they’d start school boys on for Greek translation. Either read his dialogues with Socrates, his “education of Cyrus” (hey, non-western!) or “Anabasis.” The last one is probably the most exciting.
Alternatively, Herodotus is fun, but you won’t read the whole thing. It is good to dip in and out of. Oh, Plutarch’s “Life of Alexander (the great)” is not too long and better than a history, because he focuses on his character and telling personal stories.
Once you get going, Plato is frikkin amazing. But you have to want it— or have a guide or group. I personally like “the Parmenides” because it is mind bending. Or the symposium to hear from a brilliant lady philosopher about the nature of love.
Oh, then if you want something fantastic, read Iamblicus’ “Life of Pythagoras.” It is very well written and will change your concept of the western world.
Hell to the fuck yeah, when you get to Plato, you have to want it. I still haven't made it through the Republic.
Plutarch Parallel Lives has a lot of really good biographies. Pick any. Hell, pick Life of Antony.
Herodotus is fun but junk. Thucydides is tough but meaty. Switching to the Romans, Tacitus Agricola is awesome.
Read Gorgias Encomium of Helen (short), I think he's the only Sophist we have, and you might think Plato was a little tough on him.
Republic is to be avoided for the same reasons. There is great stuff in there, but maaaan. Will check out your recs!
Also, what should I read if I like the poetry of Pope, but I want the poetry to be grittier and truer to the tone of the original, (i.e. I'm fine with changes to the content for the sake of poetics, so long as they don't hide or transfigure the original's emotional content).
BTW, watch Troy with Brad Pitt. It's got its points but it really deemphasizes the gods. It takes liberties but it's fun.
Then read the Odyssey. The Odyssey is a little stranger because it's kind of told backwards.
Then Virgil's Aeneid. Virgil is 'plagiarizing' Homer and steals a minor character Aeneas; so it helps to know the Iliad+Odyssey to get the homage. There is a really good course/podcast on the Aeneid by Susanna Braund from Stanford.
https://podcasts.apple.com/us/podcast/virgils-aeneid/id38423...
There is also the Harvard class, the Ancient Greek Hero, which may help.
https://online-learning.harvard.edu/course/ancient-greek-her...
Thucydides The Peloponnesian War has great parallels and lessons. In the middle of the war, some idiots ( Alcibiades) decide to attack Sicily because it was going to be easy and the war will pay for itself; they get their asses kicked. You can read this as an allegory for Iraq, an expensive pointless distraction led by idiots. There's also the Siege of Melos.
Yale has a good course by Donald Kagan (Project for a New American Century Donald Kagan) that has background for all this.
https://oyc.yale.edu/classics/clcv-205