What is the likelihood that the Thousand-years of pain jutsu can score a painful hit against Kages, Sannins and s-rank shinobis? This is assuming it is an actual fight and not an ambush. Here's my take: 1) It will involve distraction, possibly use of clones or genjutsu; 2) It will obviously require close distance, which is difficult considering these are pros; 3) It will require an immediate finishing move, otherwise it will only piss-off the recipient. Yes, this is a legit fight, since Naruto actually used the move when fighting against Gaara (in semi-Ichibi mode, no less), to which Pakkun the ninja dog commented "He's good." Who would be the most difficult to hit with this jutsu? (My bet is on the Raikage, with his lightning armor) So, let's hear some scenarios...