In the "He Can Smell Fear" photo, he could pass for a guy with an eclectic sense of humor and his gal-pal trying (too hard or not hard enough) to be edgy and sarcastic. Really, in that one, if you didn't know him, he could come off as a store clerk trying to cheer up an angsty Wednesday Adams. Of course, after reading the Wiki, we know better.
Really, I can't tell him apart from the preppies I went to school with. And then you look at that damn Medallion and your brain tries to rationalize that it's not weirder than wearing a KISS shirt as a sort of self-defense mechanism.
Of course, that's not a "family" picture, except in the sense of the extended "family" of CWC insiders.