Jiraiya hands down, He trained Nagato and Konan, and was pretty much like a father to Naruto, I loved the part when he got him some clothes and said something about a good bird need pretty feathers or something, no other moment in the show period quite tugged at my heart strings when Jiraiya was killed by pein, and Naruto blamed Tsunade, I nearly shed a tear or two, and that's rare for me, only time I ever cry now is at Funerals, but Jiraiya's death almost got me. Jiraiya most definitely