My friend David sent me a link to a website called Yearbook Yourself. Basically, you upload a picture of yourself and it shows you what your yearbook picture would look like every few years from the early 50s to 2000 using hot hairdos from the times. It's amazing and a total time-suckage website, so beware.
Here is David's yearbook picture from 1978:
And here are some of mine: