Brian Kernighan (of K&R fame, and much more) interviewing Ken Thompson (initial author of UNIX, though you probably already knew both of these): lots of interesting anecdotes, like getting a chess machine seized by the US government:
https://www.youtube.com/watch?v=EY6q5dv_B-o
Drew DeVault, (sway/sr.ht/much more author) hacking on his Wayland VR desktop inside of his Wayland VR desktop (don't believe the people who say you can't do programming inside of VR yet!):
https://spacepub.space/videos/watch/f60bee0e-31d3-4aca-9e49-...
NB. the second video is on a PeerTube instance. PeerTube is a federated and decentralized YouTube alternative.
Inventing on Principle: https://www.youtube.com/watch?v=8QiPFmIMxFc
Future of Programming: https://www.youtube.com/watch?v=8pTEmbeENF4
https://www.youtube.com/watch?v=hEDCXTpx0R8 OCAP 2017 Keynote Norm Hardy -- Much oral history about KeyKOS and successor systems by Norm Hardy (sadly now deceased), who was one of the main originators of them.
https://www.youtube.com/watch?v=EVm938gMWl0 RustConf 2017 -- Closing Keynote: Safe Systems Software and the Future of Computing by Joe Duffy -- Joe Duffy's retrospective talk on the Midori project at RustConf 2017.
There's a lot of stuff out there, but I thought I would drop these three in particular because they don't have particularly high viewership compared to their historical value as anecdotes.
https://www.youtube.com/watch?v=GtkouFS-GSQ
Inventing on Principle:
https://www.youtube.com/watch?v=8QiPFmIMxFc
REST/GraphQL alternative:
https://www.youtube.com/watch?v=VSKoVsHs_Ko
IMO, everything about this scene is fantastic, starting with the fact that the bits of text are taken from actual court proceedings.
Especially the first part where he explains history of lean during and after WW2.