Clowns as a horror device are relatively new. You can thank Edgar Allen Poe, Ruggero Leoncavallo's Pagliacci opera, and actual clown serial killer John Wayne Gacy for planting the seed and of course, Stephen King's It for nurturing it to get what we have now. You'll be hard pressed to find a person who actually likes clowns. 

Anime, like other modes of popular entertainment, has also created its share of sinister jokers, jesters, and pierrots to give audiences the heebie-jeebies.

1. Buggy (One Piece) 

You're sailing the high seas in search of treasure while building long-lasting friendships with your rough-and-tumble crew when, all of a sudden, you're ambushed by pirates! 

But these pirates aren't the bearded, peg-legged types. No, these circus freaks of every kind answer to a hyper-sensitive clown. 

Buggy's sensitivity is tied to his round, red nose. Yes, his schnoz isn't ornamental, it's the real deal, and he's been known to slaughter whole villages for any perceived slight against his nose. 

 

2. Quetzalcoatl (Beelzebub) 

This demon has little in common with the colorful Mesoamerican deity, opting instead for a mostly black color scheme. He wields some control over lower-ranked demons in Behemoth's 34th Pillar Division, but he's also more interested in tests of wits. 

He'll trap his opponents by setting up "game" challenges with deadly consequences, turning something as innocuous as Sudoku into a life-or-death situation. 

3. Joker (Black Butler: Book of Circus) 

There's room for sympathy with Joker. While he serves as an antagonist for Ciel and Sebastian, he had the unfortunate luck to end up the butler for an insane noble named Kelvin with a fixation on children. 

Kelvin keeps the circus members' younger family members in a faraway workhouse under his control, so he can blackmail them into doing what he wants. 

This proves enough motive for Joker to help facilitate the grisly deaths of numerous other children for Kelvin's enjoyment. Even in his last moments, Joker continues to protect Kelvin despite the human cost. 

4. Hisoka (Hunter x Hunter) 

A sadomasochist through and through, Hisoka only allows his opponents to live if he thinks killing them later will be more satisfying. 

He has little to no regard for the considerations of others and will flip alliances at the drop of a hat. Even more sinister is Hisoka's close tie between violence and sexual satisfaction. 

He isn't discriminate about his opponents' age or sex, even showing off his literally glowing manhood to Gon. Hisoka is a murderous predator in jester make-up and the last clown you'd want to invite to your kid's birthday party. 

5. The Earl of Millennium (D.Gray-man) 

While in his "Clown" form, the Earl is depicted as grinning and happy-go-lucky, with a goblin-like face and top hat. Sure, the teeth are sharp, but it's nearly enough to get you to let your guard down. 

He certainly doesn't look like someone bent on the destruction of humanity. But the Earl's hatred for humans runs deep, and underneath his somewhat eerie veneer is a completely deranged fiend still reeling from battles of his past. 

He prefers to turn humans into akuma and then use mind control so they obey his every wish. 

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6. Donato Porpora (Tokyo Ghoul)  

The Clowns of Tokyo Ghoul are the series' very own ghoul Illuminati, staying in the background despite having a hand in many major events. 

The Clowns are headed by the particularly twisted Donato Porpora, a monster who would give Hannibal Lecter a run for his money. Posing as a Catholic priest, Donato opened his own orphanage where he reviled in torturing and eating the "adopted" children and feeding them to his other wards without their knowledge. 

He's known as "Crown" among his fellow Clowns, a masked organization that continues to evade the CCG and infiltrate other ghoul social groups despite various attempts to eradicate them. 

 

7. Mad Pierrot (Cowboy Bebop)  

Cowboy Bebop is many things. It has episodes dedicated from everything to humor in "Mushroom Samba" and the tragic effects of war in "Jupiter Jazz." But rarely is Cowboy Bebop pure horror like the tale presented in "Pierrot le Fou" ("Requiem for a Clown" in Japanese). 

Like most of the clowns on this week's list, the titular Pierrot does not wear traditional clown makeup, opting instead for an exaggerated grin and an outfit reminiscent of Batman's Penguin. 

Mad Pierrot is terrifying, not just for his ghoulish grin but because of his aptitude with firearms, superhuman reflexes, and a frightening child-like innocence. 

His final confrontation with Spike, where he cries out for his mother amidst a surreal parade of Disney-like characters, will stick with you long after its over. 

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(source:animenewsnetwork)