Legend, I tried to +rep you but it turns out you have been awesome somewhere else recently and it wont let me give you any more
First thing that popped into my head. Anything by this guy: XKCD! Need I say more? Honorable mention. Open BSD is the only OS (that I know of) where they release a song with every new release. Not a video but still... http://www.openbsd.org/lyrics.html
For some reason, the only thing that sprang to mind isn't quite a music video, but still makes me giggle with glee every time I see it. It is really quite NSFW as I think the title will suggest, both the audio and the video, due to much swearing, manys profanity, wow. Geeky nonetheless.