One of the most typical behaviors of an anime villain is for them to smile wickedly. It serves as a device to allude to their derangement and hint at how they revel in the suffering of others.

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Although this trope encompasses countless evildoers, there are a few antagonists whose wicked grins can send chills down the spines of audience members every time they're flashed. By identifying them, we can better appreciate how a good smile can frame their sinister motives and establish them as credible threats before their plans have ever even been put into motion.

10 Haumea's Smirk Is Wicked & Unhinged (Fire Force)

Haumea posing in Fire Force.

Haumea is one of the most optimistic members of the White-Clad and is responsible for leading them in numerous missions against Tokyo's defenders. She is almost constantly smiling, with her cruel rictus only widening after she has put her enemies under her sway with her ignition ability.

In addition to her typical grin, she is sometimes prone to extending her tongue out for a gesture that is both silly and frightening. As a result, she remains among her organization's most memorable and deadly characters.

9 Shigaraki Rarely Grins, But It's Terrifying When He Does (My Hero Academia)

Tomura Shigaraki In My Hero Academia

Tomura Shigaraki's petulant disposition suggests that he rarely smiles, even in the presence of his master. It's for good reason, though, seeing how the League of Villains was placed in a difficult spot after the defeat and imprisonment of All For One.

When Shigaraki does choose to smile, it's usually on the cusp of a massive victory. The most memorable instance can be seen when he confronted Izuku Midoriya in public, quietly wrapping his fingers around the young hero's throat. At that moment, Deku's life was (literally) in his hands, prompting a rare and pronounced grin.

8 Meruem's Most Crooked Smiles Happened Shortly After His Birth (Hunter X Hunter)

Meruem eating in Hunter x Hunter

Once the King was finally born, he only understood brutality. During his initial raid against the NGL and the conquest of East Gorteau, he feasted upon the corpses of the nation's unprepared defenders.

As he ripped the sinew from their bodies and stained his teeth in their blood, he flashed one of the broadest and most unsettling grins in the entire series. The other Royal Guards watched in awe, associating Meruem's sadism with his personality and redoubling their efforts to serve his every whim.

7 Nnoitra Enjoyed Sneering At His Enemies (Bleach)

Ichigo Fights Nnoitra in Hueco Mundo Bleach

Nnoitra was the fifth member of the Espada and debatably its most dangerous. He enjoyed inflicting misfortune on others, as proven when he conspired with Szayel in order to cast Nelliel into the cold and unforgiving desert.

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The villain's features were usually twisted into a wide and condescending grin, one maintained during his fight with Ichigo Kurosaki. However, he lost his smile when Kenpachi challenged and defeated him, having managed to punch through his resilient Hierro in order to cause grievous injury. Ultimately, Nnoitra would provoke the shinigami into taking his life.

6 Doflamingo Often Tormented His Victims With A Huge & Cruel Smile (One Piece)

Doflamingo in one piece

Doflamingo frequently smiled, and with good reason. He was simultaneously a celestial dragon, a member of the Seven Warlords, and the king of Dressrosa.

The villain particularly enjoyed gloating over the misfortune of his enemies. As he forced King Riku to rob and butcher his own people, his grin could not have been larger. Doflamingo's massive smile is only rivaled by his bitter scowl when one of his plans has been disrupted by Luffy or Law.

5 Orochimaru Loved To Tease His Enemies As He Fought Them (Naruto)

Orochimaru kills Hiruzen in Naruto.

Considering Orochimaru's pallid complexion, rasping voice, and serpentine qualities, his appearance is already sinister enough. However, his smile adds the final piece to a frightful canvas, especially when his tongue extends far outside of his mouth.

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Perhaps the most disturbing part of the fallen Sannin's grin is his ability to shift faces. During his fight against Hiruzen Sarutobi, he assumed a feminine likeness as he scorned his former mentor. Such actions made the Third Hokage realize how willing Orochimaru was to defile shinobi conventions at his leisure.

4 Mad Pierrot Couldn't Stop Smiling (Cowboy Bebop)

cowboy bebop mad pierrot holding his hat

Mad Pierrot was a former test subject who was tortured to the brink of insanity. His mind was broken so utterly that by the time he escaped his cell, it was virtually impossible for him to stop smiling.

With a creepy grin, he hunted Spike Spiegel solely for the fact that the bounty hunter crossed his path and survived. The only thing capable of making Pierrot lose his iconic mania is the shrill cry of a cat, as he associates it with the trauma he faced while his body was being transformed.

3 Marik's Darkest Smiles Were When His Alter Ego Was Present (Yu-Gi-Oh!)

Yami Marik Yugioh smiling

Similar to Yugi, Yami Marik was the evil presence that dwelled within the Millennium Rod. Unlike the Pharaoh, whose actions were mostly a force for good in spite of his occasional spurts of brutality, Marik was actively sinister and even treated his own henchmen as disposable pawns.

Although there aren't many differences between Marik's regular form and his darker self, it is easy to distinguish who is in control by the way his hair is styled and whether or not his features are scrunched in a sinister grin.

2 Cioccolata Gleefully Butchered The Innocent (JoJo's Bizarre Adventure)

Cioccolata golden wind

Cioccolata was handily the most wicked henchman in Diavolo's service. Alongside Secco, he used his "Green Day" Stand in order to massacre dozens of people simultaneously. Their choked cries brought him visible joy, and he hoped to visit a similar fate upon Bucciarati's team.

However, Mista and Giorno were able to defeat him by continually moving upward -- the only way to negate his Stand's effects. As he plummeted to his death, Cioccolata finally lost his twisted sense of humor and cried out in despair.

1 The Major Never Stopped Smiling Even After Being Killed (Hellsing)

The Major observes London's destruction

The Major was the leader of the Millennium organization who only sought to cause as much death as possible. Regardless of how many comrades had been defeated and even when his personal safety was at risk, he never stopped smiling.

After Integra breached his zeppelin and struck him down, she realized how he could keep such a steady disposition the entire time -- he was actually a cyborg. Despite his failure to obliterate London entirely, he knew his actions caused significant enough damage to make the long wait for his attack worth it.

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