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A few of Bryan Cantrill's talks have already been mentioned here, but this one about DTrace, from 2007, is a gem: https://www.youtube.com/watch?v=TgmA48fILq8 I especially like the part in the middle where he tells the story of how a an awful GNOME applet was killing a Sun Ray server, and how he tracked down the culprit with DTrace.
https://www.youtube.com/watch?v=idLyobOhtO4
https://www.youtube.com/watch?v=MC1EKLQ2Wmg
2 Matt Godbolt (the man behind GCC explorer) - Emulating a 6502 system in Javascript
Great talk about BBC micro and much more
https://www.youtube.com/watch?v=7WuRq-Wmw5o
3 Matt Adereth - Clojure/typing
History of keyboards and a custom keyboard written in Clojure
https://www.youtube.com/watch?v=uk3A41U0iO4
I like the 3 for their content and how each speaker presented the background and their project/hack/ideas.
Highly recommend
Aside from the typical, I watched Damian Conway "Standing on the shoulders of giants" from YAPC 2016 last week and found it interesting. Always fun to see a modern feature full language collide with history and algorithms. https://www.youtube.com/watch?v=Nq2HkAYbG5o&index=2&list=PLA...