Many people cringe when they look at old yearbook photos. The braces. The hair. The fashion. The smile (or lack thereof). At the same time, yearbook photos are an ideal data set for researchers. The set-up, framing, size, and proportions have largely remained unchanged. This video profiles a UC Berkeley researcher who is mining more than a hundred years of photos to write advanced algorithms that can tell us all sorts of things--beyond regretful haircuts.