Jiraiya and obito. For jiraiya because his whole life was pretty much worse for anyone and he never gave up. He couldnt save his teacher, pupils and his best friend. He gave up his life just so he could be 100% sure about pain's secret and when he did die, it was with a smile on his face. For obito because he was alone for most of his life and was pretty much brainwashed into madara's way of thinking because of his grief over rin. Although he has become one of the worse people in ninja history, he is still in my opinion that little boy who had "dirt" his eyes and is scared that he will screw up.