In the annals of Naruto history, the Konoha shinobi and his comrades fought many despicable villains. Whether it be in his early years or the Naruto Shippuden era, there were just so many rogue ninjas found in the bingo books (i.e. the fugitive logs). They also fought quite a few terrorists who formed groups secretly.
That's why villages like the Hidden Leaf needed groups like the ANBU and Root. It didn't help that outside of these criminal elements, nations were in political conflicts and becoming enshrouded in war. With that in mind, here is a list of the nastiest, most irredeemable villains found in the franchise before the Boruto era began.
10 Danzo Shimura Was a Devious Naruto Villain
Danzo Pushed a Nasty Civil War
Danzo was always jealous of the Third Hokage (Sarutobi Hiruzen). It led to him corrupting the Root and soldiers like Sai. Most of all, he was a key factor in attacking Itachi and Shisui, which knocked over dominoes and started the Konoha civil war with the Uchiha clan.
All of these things led to Hiruzen's death, Sasuke going rogue, and Danzo implanting Sharingans in his body to become a weapon of mass destruction. He was a power-hungry tyrant who operated selfishly and had no problem killing innocents in his own village to achieve his goals. That's why fans were glad Sasuke killed him: he cost too many lives and destabilized Konoha for years.
9 The Akatsuki Were Murderous Criminals in Naruto
These Psychopaths Loved Destroying Villages
Now, it's hard to really pick individuals from the Akatsuki. They were all so heinous. Kisame, Deidara, Sasori, etc. loved sowing political discord, starting wars, and watching women and children die along the way. It broke Itachi, because he had to stomach all this when he went undercover.
Unfortunately, other key Konoha-nin would die, too. Hidan killed Hiruzen's son, Asuma, for example. Not even Naruto would vouch for members of this group to be redeemed. Other than Itachi, Naruto knew none of them could atone. They saw murder as a game or a means to an end, so not even diehard fans wanted them to get a second chance.
8 Naruto's Zabuza Was An Arrogant Maniac
Zabuza's Ego Ruined Haku's Life
Zabuza was a villain that Naruto encountered in his first real mission. Kakashi and Naruto fought Zabuza and his sidekick, the young Haku. The latter two would die, but Naruto was left scarred mentally. He hated how war, poverty and politics forced kids like Haku into a life of crime.
However, Zabuza had to take his fair share of the blame. He weaponized Haku and gaslit him into thinking he was his 'father.' It's why, after Zabuza died trying to protect Haku's body from other criminals, it's hard to sympathize with him. He was the one who created this path, only to regret it after realizing he was a monster who taught Haku that killing was a solution. Death became his karma and penance.
7 Tobi Caused Too Much Chaos in Naruto
Tobi Outweighs Obito's Heroics
Now, Tobi is the villainous side of Uchiha Obito. He was the masked man manipulating the Akatsuki's seniors. Little did Tobi know he was a puppet for other villains. This led to the Fourth Great Ninja War and many people being killed. Apart from Asuma, Neji died, along with Shikamaru and Ino's fathers.
If Tobi didn't use the Akatsuki, none of this would have happened. Even though he saw the light, returned to his Obito persona and helped Naruto out, it's hard to truly forgive him. Sure, Obito went into the afterlife, but he took many innocents with him. He should have known better after being trained by Naruto's father, Minato. Rin's death was no excuse to turn evil, as it's not what she would have wanted. Most of all, Tobi led to the death of Naruto's parents and Kurama being stored in the boy. Had Minato lived, peace and unity may well have been brought forth earlier and the Akatsuki stopped before they caused true damage.
6 Naruto's Uchiha Madara Was a Genocide Lover
Madara Slaughtered Many In Two Lifetimes
Madara was the one pulling Obito's strings. He orchestrated so many incidents that led to Obito turning evil, it's hard to keep track of the collateral damage. These mass casualties go back to his time fighting Hashirama Senju (the First Hokage). Madara was the one who kept the Uchiha clan cynical and bloodhthirsty.
When Madara died and was revived for the Fourth Great Ninja War, he once more murdered thousands of soldiers. This was before and after he became the Ten Tails Jinchūriki. He was another villain Naruto knew he had to kill in order to stop the bloodshed.
5 Hatake Sakumo's Supposed Friends Were Maniacs in Naruto
Konoha's Snobbish Pushed Him to Suicide
Sakumo was Kakashi's father and a brilliant ninja. Sadly, he was vilified after he abandoned his mission to save colleagues he considered friends. These very people, along with other Konoha citizens, labeled him as weak, and insulted him.
It pushed Sakumo into a depression. He took his own life. Now, this is a sadistic kind of villainy. Only true scum would lambaste a war hero for doing the right thing. Kakashi went dark after this, but he forgave everyone in time. Still, these people didn't deserve it. The drama proved that Konoha had vile people inside its own four walls to deal with. This was the reason Kakashi would mentor and befriend Naruto. He hated seeing Naruto become an outcast due to the Nine Tails being inside him. He knew how alienation could damage someone.
4 Kabuto Racked Up Too Many Deaths in Naruto
The Mad Scientist Had Way Too Much Red In the Ledger
Kabuto was the scientist who got manipulated by Tobi and Madara to turn against Konoha. He wanted to surpass Orochimaru, which led to him reanimating many zombies, from Madara to Itachi to other Hokages. All so the villains could have puppets.
This led to a lot of deaths. In fact, even before this drama, Kabuto was triggering wars, causing massacres, and using people as experiments. Naruto got him to make a U-turn, but Kabuto's fiendish ways may well be why the Boruto era doesn't focus on him too much. Kabuto is taking care of orphans, but it's ironic, as he led to so many being created in the first place. Rival villages will forgive, but they won't forget.
3 Naruto's Orochimaru Had No Conscience At All
The Snake Ninja Enjoyed Torture
Orochimaru betrayed Konoha, caused many deaths, like Hiruzen (his former teacher), and tried to hurt Sasuke and Itachi along the way. He even joined the Akatsuki. In short, he accumulated a ton of red in his ledger. He'd eventually renege on his ways, and join Naruto's side. However, Shikamaru still won't trust him in the Boruto series, as he rightfully sees no compassion or empathy in him.
Orochimaru killed many kids, so Konoha is monitoring him, as he supposedly works on scientific jobs in his absolution arc. Shikamaru has said, though, this is just a kinder prison. They know Orochimaru cannot undo the dominoes he kicked over, which led to Madara getting a more vulnerable shinobi world to capitalize on and exploit. Naruto might have some sympathy, but no one else thinks the snake ninja is tragic. Especially not after more experiments created Log and the young Mitsuki.
2 Kaguya and The Zetsu Are A Three-In-One Terrorist Punch in Naruto
The Kaguya Army Murdered For Fun
When the Sage of the Six Paths sealed Kaguya away, he had no clue she left contingency plans to resurrect her. This was the Black and White Zetsu: her will and 'children.' They executed her vision, manipulating Madara into assembling the Ten Tails. Thus, they and Kaguya were responsible for the millions that died in all the wars.
When the Zetsu twins brought Kaguya back, she slaughtered a lot more. All so she could try to enact the ultimate genjutsu -- the Infinite Tsukyomi. She wanted to put everyone to sleep and devour their chakra. She had lost faith in humanity, moving from being the benevolent Rabbit Princess to someone bitter. Luckily, Naruto's crew sealed her away and destroyed her minions, knowing she wouldn't stop until the world became a chakra-depleted husk.
1 Jiraiya's Orphans Wreaked Endless Havoc in Naruto
Nagato, Pain & Konan Became Crimson Puppets
Nagato and Konan turned evil after Jiraiya trained them as orphans and left. Once Yahiko died, they turned him into the Pain machines, started the Akatsuki and decided to use terrorism to bring about order and peace. They killed many families along the way. They stand out ahead of the other Akatsuki members, because this trio did think they had a higher calling and something of a more spiritual purpose.
They planned to stop murdering, but after Naruto's army fought them, they lost credence. Killing Jiraiaya didn't help either. It affirmed that they lost their souls along the way. Even after Nagato and Konan tried to make amends, the damage was done. Konoha might have been resurrected, but countless others couldn't return from the grave. In the end, without them, Kaguya's plan wouldn't have come to fruition, so they must be held accountable for their sins. Kaguya was a haughty god who didn't know better; the Akatsuki seniors, though, should have, as they knew about suffering and agony. Jiraiya taught them as much, so history cannot be sanitized. His charges were monsters and wannabe dictators, too.
