The bolded... is so cruel, but it made me LOL. XD XD
Itachi's was very sad because out of the antagonists of the series, he was my absolute favorite. And then we all find out who he really was and that he was actually good, and TEARS WERE SHED!! <3 Then, when he came back again as a Reanimation and left again... GUH. :NO: Minato and Kushina's deaths depressed me because, even while Kushina said that one of them should live to look after Naruto, they both die! Although, the redeeming part of their deaths is that Naruto still had their faith instilled in him. Their love still reached him. So, I ended up crying out of happiness when we found that out.
Now J-Man's death... I cried like a wee baby when he died. I mean, Naruto still had Kakashi and Iruka and Yamato as senseis, but Jiraiya was his master. Jiraiya was his godfather and pretty much the only actual family Naruto had left (yes, I consider godparents to be legitimate parts of a family; Sirius Black, anyone?). I mean, while he learned about Minato and Kushina's death later, Jiraiya's death was the one that impacted him the most. He was depressed, and he moped around, and for a while there, he wasn't the Naruto we all know. Yet, Naruto did was he does best and somehow overcame it.
Okay, maybe that last paragraph was meant for the Naruto FC, but I'm still on-topic here haha!