Missingno and catching Mew is how I got into cybersecurity, lil pseudo-UAF memory corruptions on 8-bit processors making the understanding so much simpler, and with a very graphic and intuitive manipulation and end effect. Pannenkoek has great stuff on floats, int overflows, etc.
If you want to learn how computers really work, study the four hour video about the mathematical edge-cases of how walls are implemented in Super Mario 64.