The following videos are related to educational technology in one way or another and worth watching. Many of these are hosted on YouTube and may have to be viewed outside of school.

An Anthropological Introduction to YouTube - hour long presentation of the YouTube phenomenon, very good
Common Craft - explanations of various technologies in plain English
Did You Know? - Karl Fisch's look at the forces changing our world and education

Education Today and Tomorrow - a look at how education is changing
Information R/evolution - explores the changes in the way we find, store, create, critique, and share information
The Machine is Us/ing Us - Web 2.0 technologies
Pay Attention - are you paying attention to the way our world is changing?
Teacher Movie - when I become a teacher...
We Think - explores the potential of the new Internet

100 Best YouTube Videos for Teachers - good list (but getting old, many videos no longer available)