I’m partial to Descartes, mainly because his writings seem to be a precursor to the thought which inspired The Matrix (probably my favorite movie). His thought experiment in Meditations on First Philosophy is quite interesting to follow and consider, where he rejects his senses due to their imperfections and destroys reality with his skepticism. He eventually comes up with his famous “I think, therefore I am” (which most people don’t understand). It’s quite entertaining to follow him all the way through to the rebuilding of reality based on what he considers to be rational truths.
Still, Descartes can be a little out there, so it’s good to read John Locke beside him. The latter takes a practical approach, suggesting that doubting reality is a waste of time because the only thing we have to go on are our senses and they seem to follow some kind of framework of rules that are always true (for example, apples grow from trees, not out of pavement). Locke is the philosopher for the pragmatic person.
George Berkeley had some funky ideas about how there probably is no reality and we are all just ideas observing other ideas, all by the grace of God. Nietzsche’s “God is dead, and man killed him” idea blew me away the first time I read about it many years ago. Lao-Tzu has some interesting thoughts about inaction being the ultimate manifestation of skill and expertise in a subject (an idea that seems pretty contradictory with the modern Western way of life). And it might be cliche, but I just love Socrates’ general attitude about life: question everything and, when you get the chance, make people look stupid using their own words.