Adding on to this question: a lot of the (really excellent) recommendations here are quite focused on the Western cannon. Are there similar suggestions for reading other schools of thought?
One of my few genuine regrets is not attending St. John's College when I was fairly aggressively courted as a high school applicant. (I may nevertheless attend one day, and be the weird old guy reading the Great Books curriculum with my new friends: several teenagers confounded and dismayed by my presence.)
The reading list for their Masters program in Eastern Classics [https://www.sjc.edu/academic-programs/graduate/masters-easte...] —while not exclusively focused on "philosophy" per se— presents a great deal of material and a framework for approaching the texts that anyone, Johnnie or not, may find valuable.
I would not recommend Wendy Doniger's works for the beginner.
She has more of a interpretive approach (which is not clearly spelled out) rather than a direct translation and hence highly controversial. Her works seriously suffer from The Danger of a Single Story syndrome (https://www.youtube.com/watch?v=D9Ihs241zeg) towards the culture they purport to explain.
I agree wholeheartedly with this caveat. Her works are really great as a non-standard (and admittedly very controversial) perspective, but can be really misleading if they are the first thing you read. I should have included something along these lines in my original recommendation, thanks!
The reading list for their Masters program in Eastern Classics [https://www.sjc.edu/academic-programs/graduate/masters-easte...] —while not exclusively focused on "philosophy" per se— presents a great deal of material and a framework for approaching the texts that anyone, Johnnie or not, may find valuable.