[rdtsc]

Pretty much anything by David Beazley or Bryan Cantrill

Discovering Python (David Beazley)

http://pyvideo.org/pycon-us-2014/discovering-python.html

David finds himself in a dark vault, stuck for months sifting through deliberately obfuscated pile of old code and manuals. All seems lost, but then he finds Python on a vanilla Windows box.

Fork Yeah! The Rise and Development of Illumos (Bryan Cantrill)

https://www.youtube.com/watch?v=-zRN7XLCRhc

History of Illumos, SunOS, Solaris, the horribleness of Oracle

These are not technical, but they are entertaining.

[ra7]

I'd also add Raymond Hettinger's talks on Python with my favorite one being this famous one:

Beyond PEP 8 - Best practices for beautiful intelligible code

https://www.youtube.com/watch?v=wf-BqAjZb8M

[wyldfire]

I'm glad you brought that dabeaz talk up, I really enjoyed that one myself.