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Highly recommend David Deutsch “The structure of reality“. From the classics, you can also add Stanislav Lem “Sum of technologies“. From the Russian classics-Carl Gustav Jung, Bertrand Russell.
Among the more modern ones – Noam Chomsky, Douglas Hofstadter. I especially recommend the latter “Godel, Escher, Bach: this endless garland“
Although in fact, you should clarify exactly which direction you are interested in. Because the answer depends a lot on it.
I would not take on such a responsibility by advising someone to read a particular book without knowing what a particular person is interested in.
If this interest is associated with the fashionable flows of philosophical thought in the modern world, then here I would read the books of Immanuel Wallerstein. Although he is not a pure philosopher. He's more of a philosopher-economist. Philosophy has long taken a materialistic position, rejecting the idea of the Creator and accepting instead man with his eternal desire to monetize everything in the world. Therefore, philosophy mainly serves either a liberal ideology, or the opposite of its idea of socialism, communism. Whatever you want, call it that.
Philosophy is no longer a method of understanding the world. For from the point of view of modern “thinkers”, the world is known and this postulate is put in bold.
But to make it clear to you what the picture of the universe is that is not presented by socialists, utopians, or bourgeois apologists for the existing system of values, start reading classical philosophy. And, to be completely honest, I would not read them either, but read all the works of one Swedish scientist, philosopher, visionary of the XVIII century Emmanuel Swedenborg. Start with his work, translated by the Russian writer S. Aksakov, ” On Heaven, on the World of Spirits, and on Hell.” This book was read by A. S. Pushkin and a huge number of our outstanding figures of culture, theology, and philosophy. This is an extremely interesting and useful book that will turn your mind upside down.
Then many philosophical works of famous authors will seem just childish babble, but the Great Book-the Holy Scripture-will become simple and understandable. Then there will be no need to search for the answers of being in philosophical works. Because the picture of the world will open up to you in its entirety.
I would recommend two philosophers:
Alexey Fedorovich Losev, I especially like the Philosophy of the name
Gennady Prokopievich Melnikov-Systemology and Linguistic aspects of Cybernetics
Both have other equally informative and interesting works.
As well as many authors from the Melnikov bibliography.
PS
Unfortunately, at the beginning of the 20th century, bibliography was “not in fashion”, so Losev has only his works.