There is a great "origin story" for "Mathematics: Its content, methods and meaning". Kolmogorov initially read a great deal of mathematics by reading encylopedias like one by Brockhaus and Efron. ( see, e.g. Tikhomirov "The life and work of Andrei Nikolaevich Kolmogorov", 1988 Russ. Math. Surv. 43 1, Page 8) This contributed to his great breadth of knowledge in mathematics.
He later felt that the encylopedia articles were too brief, and must be somewhat more elaborate. He spent a great deal of effort in "The Great Soviet Encyclopedia", and wrote some classic articles like the one on "Probability Theory". Later, with other distinguished mathematicians like Ladyzhenskaya and Sobolev, he formulated the great tri-part volume "Mathematics: Its content, methods and meaning". Great for a budding researcher in mathematics.
A modern successor to this kind of effort is "The Princeton Companion to Mathematics", which is an encylopedia of mathematics for the mathematician.
Another historical anecdote is Kolmogorov's famous visit to India. I have heard Soviet mathematicians who were students at that time, asking excitedly about his visit, like did he have to sit on top of trains? Kolmogorov laughed and said that the trains were quite comfortable. An amusing pic has Kolmogorov in dhoti and kurta, with the Indian statisticians standing around him with pants and shirts: [1]
Getting good books are really difficult these days. Nothing is more enjoyable than having your Sunday coffee while reading a good book.