Jiraiya was the most influential person in Naruto's life. His kind heart and incredible skill made him one of the best ...
Naruto and Sasuke were far from being the strongest ... but his strengths as a sensei. In his base form, Might Guy wouldn't stand a chance against any Sannin, Kage, or Akatsuki member.
There have been plenty of emotional confrontations in the Naruto franchise, with these examples being some of the best.