"The Mythical Man Month" (1975) - because human nature hasn't changed
"The History of Fortran I, II, and III" (1979) - because this historical piece by the author of the first high level language brings home the core principles of language design [https://archive.org/details/history-of-fortran]
"The Unix Programming Environment" (1984) - because the core basics of the command line haven't changed
"Reflections on Trusting Trust" (1984) - because the basic concepts of software security haven't changed
"The Rise of Worse is Better" (1991) - because many of the tradeoffs to be made when designing systems haven't changed
"The Art of Doing Science and Engineering: Learning to learn" (1996) - because the core principles that drive innovation haven't changed
"xv6" (an x86 version of Lion's Commentary, 1996) - because core OS concepts haven't changed
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