For the User Experience people: Bill Buxton is a genius. Got me sketching. (And redefined "sketching.") 1.5 hr. lecture. Teaser: includes the phrase "Charlton Heston flying through the air." Oh and also please buy Sketching User Experiences. Operators are standing by.
For the type nerds: Erik Speikermann is my idea of what real men are like. The opening jingle made me shoot beer through my nose. 6 minutes. Just watch it. Check out his blog too.
For Architecture Geeks: Stewart Brand is brilliant and insane. Fun SF footage too. Feature length PBS type thingy: Part 1 of 6.
For Anyone Who Uses a Computer: Doug Engelbart is my hero. "Dealing lightning with both hands," indeed: this is the public debut of the freaking mouse, hypertext, screensharing and the networked office. This is where it all went down, in 1968 San Francisco (think about it), to a standing ovation in a auditorium full of geeks who had their minds blown. (Bonus points if you know Stewart Brand's connection.) Long and really boring honestly. Use this like TV Guide, but watch the video on Youtube. If you look close you can see Skype crash.