Yearbook Yourself is a cute, enjoyable site. You upload a photo of yourself, and the site grafts your face into yearbook photos from different years. Some of 'em are pretty funny (and frighteningly accurate). For instance, here’s Me today, and the simulated 1964 yearbook pic. Yikes. I think I remember those glasses and that hairstyle.
(NOTE: The site is apparently supported by various shopping malls, and your yearbook photo will be displayed beside links to fashion suggestions, which are easily ignored by those of us who are allergic to fashion suggestions.)