6. These Dogs Don't Hunt
Short Version: Mitt Romney "let the dogs out" with some young black guys. Because when you're with young black guys, that's what you do, right?
Less-Short Version: Speaking of cringe-inducing old guy moments, at least one Mitt Romney moment from January 2008 needs very little comment. The candidate in Jacksonville, FL, meeting a friendly group of young African-Americans, jovially speak-singing for no rational reason that anyone can come up with to this day, “Who let the dogs out, who-who-who...” Who indeed, Governor.