Naruto: Shippuden's final episode aired over six years ago, but the series is still frequently mentioned as one of the most beloved anime franchises of all time. Naruto Uzumaki's journey to become a prolific Hokage has defined a generation of shonen anime, but Naruto's many adventures also feature encounters with a variety of memorable figures.
While many of Naruto's best characters are virtuous, straightforward individuals, there are also many conniving villains that repeatedly threaten the stability of the shinobi world. These crafty antagonists range from up-and-coming ninja to ancient beings, but they're all as deceitful as they are dangerous.
10 Sasuke Uchiha Isn't Afraid To Manipulate Those Close To Him
First Appearance: Naruto, Episode 1
Sasuke Uchiha's role changes drastically throughout the Naruto franchise, but despite his benevolent actions as a member of the Hidden Leaf Village, there's no denying that he's a bona fide villain at important points in the narrative. Sasuke never struggles during his time as an antagonist whenever it comes to the manipulation of other individuals to carry out his wicked deeds.
Sasuke spends most of Naruto and Naruto: Shippuden pursuing revenge against his brother, Itachi. Sasuke repeatedly proves that he'll stop at nothing to accomplish his goal. Although the broody Uchiha Clan member often abandons strategy for a more direct approach, he purposefully manipulates characters like Naruto, Sakura, and Karin — all of whom have strong feelings for him — enough to qualify as one of Naruto's most conniving villains.
9 Kakuzu Has Survived Since The Era Of The First Hokage
First Appearance: Naruto: Shippuden, Episode 71
The Akatsuki is full of mysterious villains, all of whom play major roles in the events of the grander Naruto franchise. However, no member goes more overlooked than Kakuzu. Kakuzu is a powerful shinobi who first rose to prominence during the reign of the First Hokage, which makes him one of the oldest characters to appear in the series.
The fact that Kakuzu is still alive after so many years is a testament to his resourcefulness. That being said, what's even more impressive is that he survives a clash with Hashirama Senju himself. This, coupled with Kakuzu's greedy habits, easily qualifies him as one of the series' most insidious figures.
8 Madara Uchiha Devises The Plan That Led To His Reincarnation
First Appearance: Naruto: Shippuden, Episode 130
When it comes to Naruto villains, none exert a more devastating impact on the series' narrative than Madara Uchiha. The legendary character once stood as a pillar of the Hidden Leaf Village, but his rivalry with Hashirama Senju eventually proves too strong to ignore and causes Madara to turn his back on the village.
Madara gets dealt a devastating defeat by the First Hokage and he decides to play the long game by bringing Obito Uchiha into the fold. This decision ultimately allows Madara to be reincarnated several decades later, at which point he successfully enacts the Infinite Tsukiyomi and becomes the strongest human in Naruto's history. Madara would likely reflect even greater long-term strategic skills and conniving tactics if not for the character's intense pride as an Uchiha.
7 Nagato Leads The Akatsuki From The Shadows
First Appearance: Naruto: Shippuden, Episode 128
Revenge repeatedly proves to be one of Naruto's most powerful motivators. In Nagato's case, this even leads him to form the Akatsuki. Characters like Obito and Madara Uchiha might try and take credit for the villainous group's actions, but Nagato plays a major role in its success.
Nagato successfully conceals his true identity for many years as he faithfully leads the Akatsuki, now as the Six Paths of Pain. This alias helps Nagato take down the legendary Toad Sage, Jiraiya, as well as demolish the Hidden Leaf Village. These destructive acts solidify Madara's status as one of Naruto's craftiest villains.
6 Sasori's Knack For Espionage Rivals Orochimaru's Expertise
First Appearance: Naruto: Shippuden, Episode 2
Sasori's first appearance helps kick off Naruto: Shippuden with a bang. The enigma initially appears to be a short, squatly figure with a long, bladed tail. However, the Akatsuki member quickly reveals that this form is merely a puppet who serves as a protective shield, which leads Sasori to eventually unveil his true form. In an effort to transform himself into the perfect puppet, Sasori reduces his living flesh to a cylindrical core. This allows Sasori to fight most opponents without risking damage to his actual body.
Sasori's grotesque technique is actually a crafty way to minimize risk against shinobi, but it's also a surprisingly helpful tactic to conceal his identity whenever he communicates with his spies. There may technically be more conniving villains than Sasori, but the fact that Orochimaru and Kabuto are wary of his knowledge speaks to his cunning nature.
5 Obito Uchiha Uses Revenge To Fuel Multiple Devastating Plots
First Appearance: Naruto: Shippuden, Episode 32
Obito Uchiha is one of the Hidden Leaf Village's most promising young shinobi before he tragically falls into the clutches of Zetsu and Madara Uchiha. Unfortunately, Obito's time with the elder Uchiha member leave him radicalized and Obito ultimately transforms into an incredibly dangerous figure in his own right.
Obito initiates the Nine-Tailed Fox's attack on the Hidden Leaf Village, sews the seeds for the formation of the Akatsuki, and conspires with Kabuto to reincarnate Madara Uchiha. These feats alone are enough to qualify him as a notably conniving antagonist, but they're made even more impressive by his ability to maintain his goofy "Tobi" persona around a group that are as dangerous as the Akatsuki.
4 Kabuto Yakushi Is The Franchise's Most Successful Spy
First Appearance: Naruto, Episode 23
Kabuto Yakushi would easily be the most conniving villain that appears on-screen in most anime, but Naruto is cut from a different cloth. The talented medical ninja doubles as a ruthlessly effective spy. Throughout the Naruto franchise, Kabuto also works alongside powerful entities like the Hidden Leaf Village, Sasori, and his despicable leader, Orochimaru.
Kabuto's affinity for espionage makes him virtually impossible to trust. Even when Orochimaru seems destined for death, this white-haired subordinate somehow finds a way to save both of their lives. Kabuto's resourcefulness and willingness to betray others would make him the series' most deceitful figure, if not for the rare displays of compassion towards shinobi that occasionally come forward.
3 Zetsu Waits For Hundreds Of Years To Initiate His Plan
First Appearance: Naruto, Episode 134
Zetsu is technically an extension of Kaguya Otsutsuki's essence. However, since they're routinely treated as separate characters, they feel safe to qualify as their own villain. Considering this, Zetsu's actions are more than enough to warrant his status as one of the most dangerous villains in anime history.
After falsifying the Uchiha Clan's records, Zetsu lays a centuries-long trap to free Kaguya through initiating the Infinite Tsukuyomi. Zetsu's immortal nature allows them to play the long con and trick even the likes of Madara Uchiha into doing their bidding. Zetsu's lack of true agency and singular goal limits his capacity for deception. However, Zetsu is incredibly motivated whenever he sets his mind to something and even the most impossible goals become within his reach.
2 Danzo Shimura Nearly Claims The Title Of Hokage Through Deceit And Ambition
First Appearance: Naruto: Shippuden, Episode 32
A character must truly be reprehensible to be considered the most-hated character in a franchise like Naruto that's so dense in villains. In Danzo Shimura's case, this reviled description isn't just apt, but the character has made a name for himself as one of the shonen genre's most despised figures.
Danzo leads the covert group known as Root, which conducts a variety of classified missions for the sake of the Hidden Leaf Village. However, Danzo's skewed perspective leads him to manipulate his position and he enables himself to do things like initiate the Uchiha massacre and steal the coveted position of Hokage. Danzo is the polar opposite of the virtuous Third Hokage and he'd be the most conniving villain in Naruto if not for the vile work or one slimier soul.
1 Orochimaru's Conniving Nature Has Made Him Virtually Unstoppable
First Appearance: Naruto, Episode 27
No villain is more synonymous with the Naruto franchise than Orochimaru. Orochimaru is an infamous shinobi who once played a major role for the Hidden Leaf Village. However, Orochimaru gets caught using his privileges to perform horrendous experiments, Orochimaru gets labeled a wanted criminal and forced into life as a rogue ninja. Orochimaru, under this new rogue shinobi status, enacts plan after plan in an attempt to obtain power, more ninjutsu, and revenge on the Hidden Leaf Village.
Even when characters like Hiruzen Sarutobi, Sasuke Uchiha, and Itachi seemingly have Orochimaru cornered, the serpentine shinobi slithers his way from danger, which all but guarantees that he will live to fight another day. In fact, Orochimaru comes to terms with the Hidden Leaf Village, which grants him the right to continue researching ninjutsu after the events of Naruto: Shippuden. This, coupled with the sheer volume of traps that he lays throughout the franchise, is more than enough evidence to assert that Orochimaru is Naruto's most conniving villain.
