Honestly, the most painful moment for me as a Naruto fan wasn't the "he was the coolest guy" (although that's painfully stupid in its own right). The most painful moment for me was the freaking 5 kage summit arc!!!!!!!!!! That arc was an atrocity regarding both Naruto and Sasuke's characters!
For Naruto, he was acting wimpy the entire arc apologizing or agonizing for his idiot friend (Sasuke). For Sasuke, 90% of the "emo" or "period" moments happened for Sasuke in this arc as well. Basically, whereas Sasuke's normally a collected avenger, he was a psychopathic lunatic.