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Even the toughest ninjas shed a tear —and so did we. Naruto Shippuden , the critically acclaimed sequel to one of the most popular anime series in history, is full of intense action, amazing camaraderie, and tear-jerking transformation. Aside from all the action and adventure, the series brought fans some truly heartbreaking moments that still reduce fans to tears.

Naruto Shippuden is the sequel series to Naruto. Created in the throes of Japan’s postwar malaise, Naruto takes place in a world undergoing a technological revolution, filled with war and conflict, on the verge of complete collapse, and follows our hero, teenage ninja Naruto Uzumaki, as he fights to save his friends, defeat deadly foes, and gain recognition within this strife-torn world. The show touches on loneliness, sacrifice, regret, and the relationship between parents and children. All themes intended to resonate with adults. That personal, intimate quality makes it have an emotional impact even outside the anime fandom.

Here are 10 of the saddest moments in Naruto Shippuden that left our hearts shattered.

1. Naruto meets his father for the first timeNaruto’s childhood was defined by a deep-rooted loneliness, having lost both parents without ever meeting them. When he finally learned that the mysterious Fourth Hokage, Minato Namikaze, was his father all along, it became a “crying ninja” moment for anime fans everywhere.

Minato’s introduction comes at one of Naruto’s lowest points, as he tries to prevent the Nine-Tails from completely overwhelming his body. Their brief, yet intense exchange, was filled with disbelief, affection and love—the type Naruto had never felt before. It was an amazing, beautiful but bittersweet moment.

2. Jiraiya’s death during the fight against painJiraiya wasn’t merely Naruto’s teacher—he was, in many ways, a surrogate grandfather. He filled our hearts with laughter through his childish friendly jokes, he still challenged and taught Naruto about strength.

When Jiraiya finally met his end in battle against his former student, Pain, he didn’t make it an easy death to swallow. His final breath around him, he still found a way to send a secret message Course Required to Save the Hidden Leaf. To see him go beneath the surface, the acceptance that he died alone but full of hope was the hardest moment to watch in one of the series’ hardest moments.

3. Shikamaru loses his mentor, AsumaThere’s a reason why Shikamaru was always so calm, so clever, so cool – he was almost always a step ahead. Yet when his team confronted the murderous Akatsuki pair, Hidan and Kakuzu, it was at a terrible price. Asuma, their sensei, was killed defending them.

Asuma’s last words to Shikamaru were profoundly touching, and his death served as a big turning point in Shikamaru’s life. This painful loss would impart to fans the lesson that even our most beloved, badass characters were not impervious to unimaginable heartache.

4. Itachi’s true story finally exposedFor years, Itachi Uchiha was vilified for the slaughter of his entire clan. When that truth came out, it changed everything.

As it turned out Itachi did it to save his younger brother, Sasuke , from becoming a civil war leader in an inevitable conflict between their clan and the rest of the Hidden Leaf. He absorbed all the criticism, suffered in solitude, and passed away without anyone ever discovering what truly transpired. His last message to Sasuke, “I’ll love you forever,” was a gut punch then and it remains one today.

5. Naruto’s parents sacrifice themselves to save himNaruto had long thought that his parents were killed in a fox raid on their village. When he does finally discover the horrible truth, the tale becomes almost impossibly sad.

In that timeline, his mother Kushina and father Minato sacrificed themselves to save baby Naruto from the Nine-Tailed Fox. They sacrificed all so he could survive. To see their last moments like this and hear their words of encouragement and support for Naruto was pretty damn brutal.

6. Neji Hyuga’s sacrifice in the fourth great ninja warWhile I can’t speak for the writers behind Neji’s development, one thing is for certain. Neji began as a very reserved, hostile character. Through the series, he underwent character development and became a man who would lay everything down on the line for his fellow companions.

As a member of Team 10, during the Fourth Great Ninja War, Neji jumped in front of an enemy attack to save Naruto and Hinata. His character’s unexpected death broke fans’ hearts and served as a painful reminder of how cruel war can be—even in an anime.

7. Shikamaru and Ino hear their fathers’ final wordsDuring a key battle in the war, Shikamaru’s father Shikaku and Ino’s father Inoichi knew they wouldn’t make it. They used their abilities to send one last message to their children before dying in an explosion.

Hearing those final words in real time, while still fighting, made this scene especially heartbreaking. It was a reminder of how much these characters gave for peace.

8. Hinata tries to save Naruto from painHinata had always admired Naruto. During Pain’s attack on the village, she stepped in to protect him—despite knowing she didn’t stand a chance.

She was beaten badly, and Naruto thought she had died. The moment triggered Naruto’s rage and awakened the Nine-Tails. It was a powerful moment of love, bravery, and loss.

9. Shikamaru breaks down over Asuma’s deathAfter losing Asuma, Shikamaru holds in his emotions—until one quiet game of shogi with his father. Overwhelmed by grief, he suddenly flips the board and breaks down.

This emotional release from such a calm and logical character showed fans a very real side of pain and mourning. It wasn’t just sad—it was human.

10. Naruto and Minato say goodbye for the last timeIn the final battles, Naruto fights alongside a reanimated version of his father Minato. They work together briefly, sharing a bond they never got to have in life.

But when the reanimation ends, Minato vanishes. Before he goes, he wishes Naruto a happy birthday—a birthday he had never been there to celebrate. Naruto sends a message back for his mother in the afterlife, closing this short but emotional father-son reunion.

Final thoughts: Naruto Shippuden balanced action with heartbreakNaruto Shippuden gave fans epic battles and unforgettable moments, but it was the emotional depth that made it truly special. These tragic scenes didn’t just make us cry—they helped us understand the pain, growth, and strength of the characters we loved.

Whether you're new to anime or a longtime fan, these moments prove that Naruto Shippuden isn’t just about ninjas—it’s about heart.