"The Longest Moment" (長き瞬間の中で…, Nagaki Toki no Nakade…) is episode 135 of the Naruto: Shippūden anime.
As Sasuke approaches the Uchiha Hideout, Itachi sits on a chair waiting for him, reminiscing on the last days of his clan. After carrying Sasuke home as he had sprained his ankle, Itachi was told by his father Fugaku to attend an Uchiha clan meeting the next day, which Itachi chose not to attend due to his Anbu priorities. The following day, he was approached by Uchiha clan members of the Konoha Military Police Force, who believed he was responsible for the murder of his best friend, Shisui Uchiha, who had also missed the meeting. Itachi fought the police officers, calling the Uchiha clan arrogant and pathetic, relenting only after hearing Sasuke's voice. Shortly after, as his mother made him dinner, Itachi had slaughtered the entire clan, sparing only Sasuke's life. As Sasuke had demanded why Itachi would do such a thing, Itachi had told him that he has butchered them all simply to test the limit of his power, and wanted Sasuke to grow powerful so that he may be a worthy opponent for him one day. Before he departed, Itachi reveals to Sasuke that the secret behind the Mangekyō Sharingan is to kill your best friend, explaining that he did kill Shisui, and if Sasuke followed in his steps, he would be the third one in the clan to have activated the Mangekyō.
Itachi is awoken from his reverie as Sasuke enters the hideout. Itachi asks what Sasuke sees with his Sharingan, to which Sasuke replies that he sees Itachi dead. The two begin fighting as Sasuke attempts to strike with his Chidori Sharp Spear; Itachi uses his Early Sacrifice technique to jump on Sasuke's shoulder, evading the attack, and spins Sasuke around before slamming him into a wall. As Sasuke hits the wall, he prepares his Chidori and rushes towards Itachi. Just as Itachi expects Sasuke to thrust him with it, Sasuke disperses the lighning chakra through his Chidori Current, and uses the opportunity to leap into the air and impales Itachi with his sword.
As Itachi falls on the ground below, he muses that Sasuke has grown strong and disintegrates into a flock of crows. Sasuke realises that Itachi has been using a genjutsu, but it turns out that the Sasuke that was fighting is also an illusion; the real Sasuke sneaks up from behind Itachi and runs his sword through him. As Itachi coughs up blood, Sasuke demands to know who else from the Uchiha clan survived. When Itachi further questions his demand, Sasuke reminds him that he was told he would be the third to awaken the Mangekyō Sharingan, meaning there was someone else out there other than Itachi who possessed it. Believing that this person aided Itachi take out the police force in the clan's massacre, Sasuke pushes the blade further through Itachi's torso as he demands to know who it is so that he may kill that person as well. Itachi responds that it is none other than Madara Uchiha, the co-founder of Konohagakure; Sasuke recalls the Nine-Tailed Fox telling him that he reminded the tailed beast of Madara from the elder days.
|Role||Seiyū||English Voice Actor|
|Sasuke Uchiha||Noriaki Sugiyama||杉山 紀彰||Sugiyama Noriaki||Yuri Lowenthal|
|Itachi Uchiha||Hideo Ishikawa||石川 英郎||Ishikawa Hideo||Crispin Freeman|
|Fugaku Uchiha||Kenji Hamada||浜田 賢二||Hamada Kenji||Doug Stone|
|Mikoto Uchiha||Emi Sagara||さがら えみ||Sagara Emi||Kari Wahlgren|
|Yashiro Uchiha||Takashi Nagasako||長嶝 高士||Nagasako Takashi||Troy Baker|
|Inabi Uchiha||Yoshimitsu Shimoyama||下山 吉光||Shimoyama Yoshimitsu||Roger Craig Smith|
|Tekka Uchiha||Kimiyoshi Kibe||岐部 公好||Kibe Kimiyoshi|