Famous friend

While I was in DC I walked around the various Smithsonian buidlings and came across this portrait competition. Some really amazing paintings and photos. The winner was a 2 by 3 foot digital print of a photo taken by Dave Woody of Colorado:



It's a strong portrait and technically a great photograph, but what really gets me is that I'm pretty sure I've met this person. Is that possible? Or is there really something about the lighting, styling, the model, etc. that just fools me into thinking that? And does it work for everyone like that, or does it have something to do with my age, my socio-economic background, my fondness of V-necks, etc.