The grainy quality of this yearbook photo lends a clue as to when it was taken, but the dated haircut and double-windsor necktie may have already served that purpose. Do you recognize that serious stare? This singer has a song about not being the most popular kid in school ... maybe if he would have smiled just a little bit more, things would have been different?

The youngster pictured here would go on to become one of the more patriotic country superstars, and would be named Billboard's most played artist of the 2000s. Have you figured it out yet? Perhaps he'd be more recognizable had he been holding onto a drinking receptacle of a certain color.