Face of an Angel, Mind of a Demon

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New rule, Somali pirates have to stop being so darn cute! This is the New York debut of the one surviving member of the apparent boy band that kidnapped that cargo ship, and the new face of evil looks like he's just hoping to see The Lion King! —Bill Maher, Real Time with Bill Maher, April 24, 2009.

Most of the time, evil characters will have a stereotypical "evil" look to them. Not these guys. These villains have the looks that are generally associated with absolute innocence. Of course, don't be surprised if they use that to their advantage.

Not to be confused with Beauty Is Bad or Evil Is Sexy, as looking attractive and looking innocent/virtuous are not necessarily associated with each other. (If anything, they are sometimes contrasted.)

Also not to be confused with the Killer Rabbit, who looks weaker than they are, but not necessarily more innocent. Enfant Terribles are often this. Contrast Face of a Thug

Examples of Face of an Angel, Mind of a Demon include:

Anime and Manga

• Johan Liebert from Monster has a pleasant, almost angelic face. He is evil incarnate.
• El Hazard 2 - while Kalia may look sweet and innocent, don't be fooled. In truth, she's an instrument of revenge, created by the lost tribes and civilizations who felt wronged by the Eye of God. Thus, she exists to wipe out all existence, and we mean ALL OF IT.
• Dietrich Von Lohengrin from Trinity Blood. In-universe, he's described as having the face of an angel but the heart of a devil.
• In Gankutsuou, this is done with Andrea, as is the case in the original The Count of Monte Cristo (see Literature below). While Generic Cuteness is in play, Andrea is still the most Bishonen cast member, and has blond Princess Curls. The only hint of his true nature as a depraved psychopath is the fact that he has rather slitted eyes which reveal themselves as Hellish Pupils when his affable mask drops.
• Glemmy Toto of Mobile Suit Gundam ZZ is a charming 17-year old with a goofy personality and the face of the bishiest pretty boy you ever did meet. He's a clone of Gihren Zabi, the UC version of Adolf Hitler and is the running for the title of "most evil person in the show".
• This is said, nearly word-for-word about the recently-deceased daughter of a couple who buy a rabbit from Count D in Pet Shop of Horrors. It turned out that said daughter had been absolutely adorable, but grew up to be a shoplifter, a drug addict, and generally a horrible person, thanks to her being spoiled throughout childhood. This comes up when the parents spoil the rabbit (who magically looks exactly like their daughter) and it promptly begins to act the same way, manipulating them into feeding it things that lets it rapidly reproduce.
• The minor villain Maurice Cole fits the trope best in Black Butler, and he wrings every drop of advantage of it. The Villain Protagonist Ciel also does a great job of turning on his charm when it benefits him, but the other end of his range extends through cold and mature to Creepy Child, which doesn't fit this trope so well. Other characters, such as Sebastian, may be extremely beautiful but lack the aura of innocence.

Comic Books

• One such character named Angelface (guess what he looks like) appears in a Blueberry story, as part of a plot to kill Lincoln. He ends up getting his face shoved into a locomotive's furnace
• Word of God says that Kroenen from Hellboy literally was a choir boy before he became a self-mutilating psychopathic Nazi ninja zombie.

Film

• The actor chosen to play the Scorpio Killer (pictured above) from Dirty Harry was chosen because he had a "face like a choir boy." Scorpio is a murdering psychopath and a Complete Monster who you will be glad to see the title character take down in the final scene.
• The title character of The Good Son.
• Dolores Umbridge in Harry Potter and the Deathly Hallows. While the book described her as ugly and toad-like, the Dolores in the film is the type you might mistake for a sweet, kind grandmother, not a mistake you'd repeat, as she's a bigot who hates muggles, half-muggles, and any sort of children, and a slavishly loyal sycophant to Voldemort.
• Villain Protagonist Damien from The Omen is literally a demon, his childlike appearance the whole reason he is never suspected of the atrocities he causes. Well, almost never, but the ones who do tend to be killed quickly, either by Damien or clueless adults he tricks into protecting him.

Literature

• Discworld
  • Played (sort of) straight in with Mr. Teatime from Hogfather, since his eyes serve as a Red Right Hand.
  • Played completely straight by Carcer in Night Watch, who could be standing in the middle of a room full of bloody corpses with a knife in his hand and say "What, me?" while looking genuinly hurt by the accusation.
• Ferahgo the Assassin from Salamandastron has baby blue eyes which make him look completely innocent. In case the latter part of his name wasn't enough of a hint, He's not.
• Done by Alexandre Dumas in at least two of his novels.
  • In The Three Musketeers, there's an inversion of the good blonde and bad brunette, as the heroine, Constance, has dark hair, and Milady, the villain, is blonde and angelic looking.
  • In The Count of Monte Cristo, the villain Bendetto AKA Andrea has strawberry blond hair (making him a case of both Blond Guys Are Evil and Evil Redhead), and there's a comment in the text to the effect that he looked like an angel; unfortunately, that angel was Lucifer.
• In the original Battle Royale, Femme Fatale Mitsuko was repeatedly described as an "angelic beauty". She convinced several of her classmates that she was in fact completely innocent and vulnerable. The movie upgraded her to Evil Is Sexy, while the manga turned her into an improbably buxom, demonic Broken Bird.
• Angélica de Alquézar from the Alatriste series. In the first book, narrator Íñigo describes her as being "as perverse and wicked as only Evil in the form of a blonde eleven- or twelve-year-old girl can be." He's head over heels in love with her, even after she gives him a "gift" which helps the Inquisition frame him for heresy.

Live-Action TV

• One of the UnSubs in Criminal Minds was 13-year-old boy who used his innocent look to get closer to people and then kill them.
• The original name given to Angelus from Angel was 'The One with the Angelic Face' which sounds nice, till you find out just how vicious Angelus was.
• CSI "Las Vegas" had Justin Bieber star as a psychotic teenage murderer.
• Fringe does this in the episode where it appears that two men are forcing people to harm themselves or even kill themselves, but it actually turns out to be the boy that is in the car with them. He is assumed to be the victim until it is revealed that he is the one perpetrating these crimes.

Music

• There's the lyrics to the Elvis Presley song "Devil in Disguise".

You look like an angel Walk like an angel Talk like an angel But I got wise You're the devil in disguise

• Johnny Rivers' "Secret Agent Man":

Beware of pretty faces that you find; A pretty face can hide an evil mind.

Theatre

• Older Than Steam: Iago from Othello. This trope's part of the reason why he's able to manipulate everyone so effectively.

Video Games

• Dahlia Hawthorne in Ace Attorney exploits this for all it's worth in every one of her appearances.
• Castor from Last Scenario. That's not how you'd imagine a scheming, megalomaniac Well-Intentioned Extremist.

Western Animation

• Lawyer Goodwill from the old (1933) Looney Tunes short "The Case of The Stuttering Pig". Despite being a bulldog, he seems to be a helpful, compassionate, friendly sort, but in truth, he plans to murder Porky and his siblings so as to inherit their late uncle's property. Downplayed slightly as, to hide his identity, he drinks "Dr. Jekyll Juice" and gives himself a horrific face that matches his soul.

Real Life

• Online scammers will often use images of a cute little anime girl asking for a credit card number, often sweetly saying "pretty please?" DON'T FALL FOR IT!
• Cracked.com presents 5 Adorable Animals That Are Turning To The Dark Side.
• Dr. H. H. Holmes, sometimes known as America's first serial killer, was said to be strikingly handsome and trustworthy looking.
• Ted Bundy was known for his handsome features.
  • Then there's the bank robber Baby Face Nelson
• This is quite common with young women who get accused of serious crimes.
  • An exemplar case here - and as far as we know a subversion as well - is Amanda Knox, who got that reputation during her trial before being acquitted in 2011. There has even been a movie about her.